Case 3:21-cv-00911-VLB Document 36 Filed 06/30/23 Page 1 of 56
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`UNITED STATES DISTRICT COURT
`DISTRICT OF CONNECTICUT
`
`In re
`Curtis James Jackson III,
` Debtor
`
`Curtis James Jackson III,
`Appellant
` v.
`Reed Smith LLP, and
`Peter Raymond,
`Appellees
`
`
`
`:
`
`:
`District Court No.: 3:21-cv-00911(VLB)
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`:
`Bankruptcy Court No.: 15-21233(AMN)
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`:
`Adv. Pro. No.: 17-02005 (AMN)
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`:
` June 30, 2023
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`:
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`
`
`MEMORANDUM OF DECISION
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`This appeal arises from an adversary proceeding connected to appellant
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`Curtis James Jackson, III’s Chapter 11 bankruptcy petition. After Jackson—better
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`known as the rapper, 50 Cent—filed for bankruptcy in 2015, appellees Reed Smith,
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`LLP and one of its former partners, Peter Raymond filed a proof of claim,
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`contending that Jackson owed them $609,235.41 in attorneys’ fees and costs.
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`Jackson lodged five counterclaims against Reed Smith and Raymond for legal
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`malpractice and breach of fiduciary duty. (AP ECF 1 (Obj. & Countercl.).)1
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`The counterclaims’ underlying facts concern Appellees’ representation of
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`Jackson in a lawsuit filed by Lastonia Leviston, a woman depicted in a sexually
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`explicit video (“Video”). She alleged Jackson’s publication of the Video without
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`her consent violated New York state law and constituted intentional infliction of
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`emotional distress (“IIED”). Jackson terminated Appellees a few months before
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`1 Citations to filings in adversary proceeding no. 17-02005 are noted by “AP ECF.”
`1
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`Case 3:21-cv-00911-VLB Document 36 Filed 06/30/23 Page 2 of 56
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`trial. With replacement counsel, the jury returned a $7,000,000 verdict in favor of
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`Leviston.
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`Appellees moved to dismiss Jackson’s operative counterclaims. The
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`bankruptcy court dismissed nearly all counterclaims except a portion of Count 2:
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`whether Appellees committed legal malpractice by failing to conduct and preserve
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`discovery of three witnesses, which, if conducted, would have mitigated or
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`absolved Jackson’s damages. (AP ECF 62 (Dec. Mot. Dismiss) at 23.) After
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`discovery concluded, Appellees moved for summary judgment on the remaining
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`counterclaim. The bankruptcy court granted summary judgment in favor of
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`Appellees. (AP ECF 395 (Dec. Mot. Summ. J.) at 58.)2 This appeal followed.
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`I.
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`BACKGROUND
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`The Court presumes familiarity with the facts and evidence but includes this
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`Background for the reader’s benefit. Because this appeal involves the bankruptcy
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`court’s decisions on the motion to dismiss and motion for summary judgment, the
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`Court will first cite to the pleadings and transition in section I.C to discussing
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`evidence relevant to the appeal.
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`A. The Parties and their Attorney-Client Relationship
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`Appellant Curtis James Jackson, III, also known as 50 Cent, is a well-known
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`rap music performer, entertainer, and entrepreneur. (AP ECF 22 (Am. Obj. &
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`Countercl.) ¶ 6.) On February 2, 2004, Jackson entered into a retainer agreement
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`2 In addition to Jackson’s counterclaims, the parties litigated his objections to the proof of
`claim. The bankruptcy court denied the motion to dismiss on three grounds: “ (1) an
`alleged violation of 22 NYCRR 1215.1; (2) an alleged conflict of interest; and (3)
`excessiveness pursuant to Bankruptcy Code § 502(b)(4).” (Id. at 57.) Appellees only
`moved for summary judgment on the third issue, and the bankruptcy court denied the
`motion. (See id.) These objections are not part of the appeal.
`2
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`Case 3:21-cv-00911-VLB Document 36 Filed 06/30/23 Page 3 of 56
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`with Appellees Reed Smith LLP and one of its partners, Peter Raymond (together,
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`“Appellees”), to represent him on certain legal matters (“Retainer”).3 (Id. ¶ 42.)
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`This Retainer is the only fee agreement between the parties. (AP ECF 22 ¶ 24.)
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`Appellees represented Jackson until they were terminated on March 27, 2015. (Id.
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`¶ 108.)
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`The Retainer contemplated the scope of representation and discharge. The
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`first sentence indicates, “We are pleased that you desire to have us represent you
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`in connection with certain of your activities in the entertainment business and with
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`respect to third party claims and lawsuits that have been filed against you.” (AP
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`ECF 22-8 at 1.) Either party could terminate the agreement “at any time by written
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`notice, subject to [Jackson’s] obligation to pay [Appellees’] fees as described
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`below and subject on [Appellees’] part to applicable rules of professional conduct.”
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`(Id.)
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`The Retainer also explained Appellees’ co-counsel relationship with
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`Jackson’s attorney, Theodor K. Sedlmayr of Sedlmayr & Associates. (Id. at 3.)
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`Namely, “Reed Smith LLP has agreed to compensate Mr. Sedlmayr for his services
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`as liaison to Reed Smith” for his services connected to Reed Smith’s billings. (Id.
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`at 3–4.)
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`B. The Leviston Action
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`On February 24, 2010, Lastonia Leviston filed a complaint against Jackson
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`in New York state court, alleging he unlawfully posted a “sexually explicit
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`3 Jackson incorporated the Retainer to his Amended Counterclaims as Exhibit H. (See AP
`ECF 22-8 (Am. Obj. & Countercl. Ex. H, Retainer).)
`3
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`Case 3:21-cv-00911-VLB Document 36 Filed 06/30/23 Page 4 of 56
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`videotape” depicting Leviston “without her knowledge or consent.”4 (AP ECF 22-
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`4 (Am. Obj. & Countercl. Ex. D, Leviston Compl.) ¶ 1.) According to the Complaint,
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`Leviston and Maurice Murray were in a romantic relationship and videotaped
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`themselves “engaging in sexually explicit activities” on June 30, 2008. (Id. ¶¶ 4–
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`6.) She intended the Video to be private and thereafter explicitly asked Murray to
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`destroy it. (Id.) However, around March 1, 2009, Murray gave or sold the Video to
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`Jackson without Leviston’s knowledge or consent. (Id. ¶ 7.) Jackson then edited
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`the Video; narrated and appeared in the edited version; published it; and then
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`publicly described Leviston as a “call girl,” “Brooke,” and the mother of a child
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`with his rival, William A. Robert II, also known as Rick Ross (“Rick Ross”). (Id. ¶¶
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`7–13.) Leviston asserted three counts— (1) violation of sections 50–51 of the New
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`York Civil Rights Law, (2) IIED, and (3) defamation—and sought compensatory,
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`special and punitive damages. (Id. ¶ 1.)
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`Jackson alleges that Appellees did not obtain certain discovery key to his
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`defense. First, Appellees did not subpoena documents from NING Interactive Inc.,
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`the internet provider that hosted the website owned by Rick Ross where the Video
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`was allegedly first published (“Internet Provider”). (Id. ¶ 16.) Second, Appellees
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`did not interview or depose Rick Ross, Murray or the Internet Provider (collectively,
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`“Three Uncalled Witnesses”). (Id. ¶¶ 17, 61.) Instead, on February 22, 2012,
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`Appellees entered into a binding stipulation agreement with Leviston’s counsel in
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`which they agreed not to call any witness to testify who had not previously been
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`4 Jackson incorporated the Leviston Complaint to his Amended Counterclaims as Exhibit
`D. (Id.)
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`4
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`disclosed and deposed.5 (Id. at ¶¶ 17, 63; AP ECF 22-6 (Am. Obj. & Countercl. Ex.
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`F, Stip.) ¶¶ 8–10.) Because Appellees never identified any of the Three Uncalled
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`Witnesses, he was not permitted to call them to testify. (Id. ¶ 68.) Jackson alleges
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`that these witnesses were “material, relevant, and critical” to his defense
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`concerning liability and damages. (See id. ¶¶ 85,93, 101.)
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`On March 27, 2015, Jackson terminated Appellees. (See id. ¶ 108.) According
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`to Jackson, Appellees “represented that they would cooperate with and provide all
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`the material, documentation, and information to Jackson’s new counsel, Bickel &
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`Brewer, but failed and refused to cooperate with new trial counsel, which was to
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`the detriment and prejudice of Jackson and caused him to be subject to an
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`unfavorable jury verdict.” (Id. ¶ 20.) Replacement counsel sought to reopen
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`discovery to depose the key witnesses, but the court denied the request. (See id.
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`¶ 103.) Trial commenced, concluded, and the jury awarded actual and punitive
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`damages in the sum of $7,000,000. (Id. ¶ 21.)
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`C. Chapter 11 Bankruptcy Proceedings
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`On July 13, 2015, Jackson filed a voluntary petition for relief under Chapter
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`11 of the United States Bankruptcy Code. (Id. ¶ 1.) Reed Smith filed its Proof of
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`Claim on November 3, 2015, claiming Jackson owes the firm $609,235.41. (See AP
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`ECF 22-1 (Am. Obj. & Countercl. Ex. A, Proof of Claim).) Jackson lodged objections
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`on October 18, 2016. (AP ECF 22 ¶ 2.)
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`5 Jackson incorporated the Stipulation to his Amended Counterclaims as Exhibit F. (Id.)
`5
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`1. The Pleadings
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`On January 27, 2017, Jackson initiated an adversary proceeding against
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`Appellees, (see AP ECF 1 ¶¶ 2, 30–32). Appellees moved to dismiss Jackson’s
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`Counterclaims on April 17, 2017. (See AP ECF 16 (Mot. Dismiss).) On May 22,
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`2017, Jackson timely filed Amended Counterclaims, which constitute the operative
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`pleading in this case. 6 (See AP ECF 22.)
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`There are five Amended Counterclaims with the following titles: (1) “first
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`cause of action for malpractice, breaching a fiduciary duty in having an unwaivable
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`conflict of interest and failing to exercise due diligence in representing Jackson;”
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`(2) “second cause of action for breaching a fiduciary duty and malpractice in failing
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`to conduct reasonably competent pre-trial investigation and discovery of key
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`material witnesses and engaging in other conduct prejudicial to Jackson’s
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`defense;” (3) “third cause of action for breach of fiduciary duty and malpractice by
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`charging excessive legal fees;” (4) “fourth cause of action for breach of fiduciary
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`duty and malpractice for pursuing litigation on a matter for which [Appellees]
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`believed Jackson did not have a viable defense for and failing to engage in
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`meaningful settlement negotiations to seek expedited resolution of the matter;”
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`and (5) “fifth cause of action for breach of fiduciary duty and malpractice in failing
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`to develop a reasonably competent defense to Leviston’s claims against Jackson
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`made pursuant to New York Civil Rights Law Sections 50 & 51 and Intentional
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`Infliction of Emotional Distress.” (Id. at Causes of Action.) In summary, each count
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`6 Rule 15 of the Federal Rules of Civil Procedure govern Jackson’s amended pleading. See
`Fed. R. Bankr. P. 7015. While normally Rule 15 only gives the plaintiff 21 days to respond
`to a motion to dismiss, the parties agreed to a response deadline of May 22, 2017. See Fed.
`R. Civ. P. 15(a)(1)(B). (See also AP ECF 19 (Order re Stip.).)
`6
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`asserts a legal malpractice claim and a breach of fiduciary duty claim for a specific
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`set of facts.
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`Appellees filed its second Motion to Dismiss the adversary proceeding on
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`June 19, 2017. (See AP ECF 27 (Mot. Dismiss).) The bankruptcy judge held a
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`hearing on May 23, 2018 and ordered supplemental briefing. (See AP ECF 48 (Audio
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`File).) The motion was fully briefed by June 28, 2018. (See AP ECF 59 (2d Supp.
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`Br.).)
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`On March 1, 2019, the bankruptcy court issued its decision on the motion to
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`dismiss. (AP ECF 62 (Dec. on Mot. Dismiss).) At the outset, the bankruptcy court
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`dismissed all breach of fiduciary duty claims that arose from Appellees’
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`representation of Jackson during the Leviston case, concluding that they were
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`duplicative because they were based on the same facts and alleged the same
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`damages. (Id. at 16–17.) The only breach of fiduciary claim the bankruptcy court
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`did not dismiss as duplicative was part of Count 2—Appellees’ failure to cooperate
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`with replacement counsel—on the grounds the alleged breach arose after Jackson
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`terminated Appellees. (Id. at 17.) The bankruptcy court nonetheless dismissed the
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`Count 2 breach of fiduciary duty claim for failure to allege causation between the
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`alleged breach and damages. (Id. at 26.)
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`As for the legal malpractice claims, the Court dismissed nearly all of them
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`for failure to state a claim except one narrow issue: as to Count 2, whether
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`Appellees’ failure to conduct discovery and preserve the testimony of three
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`witnesses “may have mitigated the amount of damages” awarded against Jackson
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`in the Leviston case. (See AP ECF 62 at 24.)
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`7
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`2. Relevant Evidence
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`The following evidence relates to the summary judgment issues on appeal.
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`i. Appellees’ Litigation Strategy
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`On January 24, 2011, Raymond e-mailed Sedlmayr and CC’d Nikki Martin,
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`Vice President of CJJ Enterprises, LLC’s (Jackson’s company), and Evan Farber,
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`an associate at Reed Smith. Raymond summarized information Jackson and
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`Martin told him, which was that Rick Ross acquired the Video and posted it on his
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`own site, that Jackson streamed the Video but did not post it, and that “no
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`advertising was sold through use of the video.” (AP ECF 335-32 (Summ. J. Opp’n
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`Ex. 31, Email 1/24/11).) Raymond added, “If we can prove that Rick Ross was the
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`uploader of the video onto the Internet, I think this will take a good deal of sting out
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`of the claims against 50.” (Id.)
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`The record contains a draft subpoena. The first is directed to Rick Ross,
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`dated “April __ 2011.” (AP ECF 335-34 (Summ. J. Opp’n Ex. 33, Draft Subpoena
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`Ross).) The draft includes a Schedule A listing all documents Rick Ross would be
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`required to bring to the deposition. (See id.) The second is directed to Murray,
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`dated “October __, 2011,” and similarly requests documents. (AP ECF 335-46
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`(Summ. J. Opp’n Ex. 45, Draft Subpoena Murray).)
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`On February 22, 2012, the parties entered into a discovery stipulation that
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`the trial court adopted (“2012 Stipulation”). Paragraph 12 states:
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`Defendant shall inform Plaintiff by May 1, 2012 if he intends to call any
`witnesses at trial other than those Plaintiff has already deposed or will
`depose pursuant to this Order. Defendant shall produce all
`documents related to such witnesses’ testimony on or before May 1,
`2012. Plaintiff shall complete all depositions of any such witnesses
`on or before June 15, 2012.
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`8
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`(AP ECF 22-6 ¶ 10.) Farber testified that he informed Martin about the plan to enter
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`into the 2012 Stipulation. (ECF 24-10 (Appeal Br. App. 10, A-2291–2571) at A-2369.)
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`Jackson confirmed he was not part of discussions about witnesses. (Id. at A-2356.)
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`Fast forward through the close of discovery to trial preparation. On
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`December 31, 2014, Craig Weiner emailed Farber, CC’ing Steve Savva, about the
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`2012 Stipulation. (AP ECF 335-50 (Summ. J. Opp’n Ex. 49, Email 12/31/14).) Weiner
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`stated: “Also please send me the stipulation regarding witnesses at trial as well as
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`any contemporaneous correspondence with the client and/or the other side. I need
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`to explain this surprise developement [sic] with the client. I must say I wish this
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`was brought to our attention when we first spoke with Peter as if we can’t call the
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`witness it means we may have spent a lot of time and money for naught. Is there
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`anything else I need to be aware of?” (Id.)
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`Later that day, Farber emailed Raymond summarizing a call he had with
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`Weiner, Savva, and the private investigator who had tracked down Murray in
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`prison. (See AP ECF 335-48 (Summ. J. Opp’n Ex. 47, Email 1/1/15).) He informed
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`Raymond that he “warned them about our stipulation against calling new
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`witnesses” after they expressed interest in finding witnesses who could testify
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`about Leviston’s past. (Id.) Farber reflected: “This was news to them (though I told
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`them we had previously told that to 50 and Nikki) and they asked that I forward the
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`stipulation to them.” (Id.)
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`On January 4, 2015, Farber emailed the case team about discovery in their e-
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`folder. (See AP ECF 335-36 (Summ. J. Opp’n Ex. 35, Email 1/4/15).) He referenced
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`9
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`an e-mail with a link to a video in which Rick Ross “takes credit for ‘This Is
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`Sabrina’s Sin’ being his website.” (Id.)
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`On January 12, 2015, Martin e-mailed Raymond and Farber about “the
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`investigator’s conversation with Murray and his brother.” (AP ECF 335–44 (Summ.
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`J. Opp’n Ex. 43, Email 1/12/15).) She asked counsel whether they could “ask for
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`more time” and whether “the calls need to be subpoenaed.” (Id.) Martin added, “I
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`have to say 50 was pretty disappointed to hear that all the while we were told
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`Murray could not be found, Steve found him with a google search. I really hope we
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`can come up with the most positive outcome possible in this matter.” (Id.)
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`A few weeks later, Sarah Levitan, a Reed Smith associate, e-mailed Raymond
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`her suggestions for his opening statement. (AP ECF 335-37 (Summ. J. Opp’n Ex.
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`36, Email 1/20/15).) She reflected: “My only other thought would be to further
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`emphasize the role both Murray and Ross played and their general poor character.
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`This may help jurors who aren’t as comfortable blaming Ms. Leviston for the
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`release of the tape blame someone else rather than 50.” (Id.)
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`On March 12, 2015, Farber e-mailed the case team about “a few thought
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`questions … for which I haven’t been able to come up with great responses.” (AP
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`ECF 335-33 (Summ. J. Opp’n Ex. 32, Email 3/12/15).) He references belated
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`production from the plaintiff, stating: “They say that we’re not prejudiced by the
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`belated production, and if we are, they’ll work with us on reasonable discovery to
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`ameliorate the prejudice. How do we respond to that? And if the Judge asks, what
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`discovery do we think we need? A dep of Rick Ross, to be sure, but what else?”
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`10
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`(Id.) Raymond responds, “A Ross depo would be great now and would solve all
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`the problems.” (Id.) He added, “But don’t know if we can get Ross.” (Id.)
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`By the end of the month, Jackson terminated Appellees. (ECF 24.2 (Appeal
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`Br. App. 2, A-243-480) at 306–07.)
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`ii. Replacement Counsel
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`On May 1, 2015, replacement counsel—Stephanie Gase, Paul Miletic, and
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`Steven Losquadro of Bickel & Brewer—Reed Smith, and Leviston’s counsel
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`appeared before Judge Wooten due to replacement counsel’s motions to postpone
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`trial and to bring a third-party claim against Rick Ross. (See id. A-302–07.) With
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`respect to the first motion, Attorney Gase explained that Bickel & Brewer was
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`retained on March 27, requested the case file from Reed Smith “[s]hortly
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`thereafter,” received the initial documents on April 3, sent “a list of everything
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`[they] thought was missing” on April 8, did not receive additional documents until
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`April 21, and determined they were “still missing a substantial number of files from
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`Reed Smith.” (Id. at A-306–07) Attorney Gase explained, “I’ve yet to be able to fully
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`prepare without getting those files.” (Id. at A-307.)
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`As for the second motion, Attorney Gase explained that Bickel & Brewer
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`wanted to seek discovery from Rick Ross, (id.) and add Ross as a “third party for
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`contribution.”7 After Judge Wooten explained that the case was filed in 2010, been
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`through “tons of discovery,” summary judgment motions, the note of issue stage,
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`and then reflected a “third party action against Rick Ross … could have been
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`concluded years ago,” Attorney Gase responded the third party claim against Ross
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`7 Page 7 of the transcript is missing from the record.
`11
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`“is something that could have been at the beginning of this litigation and was not
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`done.” (Id. at A-308.) Judge Wooten denied Attorney Gase’s request, expressing
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`concern for preserving judicial economy and avoiding prejudice to Leviston. (See
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`id. at A-309–10.)
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`Judge Wooten permitted Leviston’s counsel to be heard on the issue of
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`adjournment. Jackson’s counsel described the process of replacing counsel from
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`the plaintiff’s vantage point. In summary, plaintiff’s counsel expressed concern
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`that Jackson’s replacement of counsel only two months before trial may have been
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`a “disingenuous” effort to prevent the trial from going forward. Jackson’s counsel
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`made several arguments. First, replacement counsel entered an appearance
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`before receiving the file even though the trial date was set to begin in less than 60
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`days, and counsel believed no lawyer would accept a case shortly before trial
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`without having the file. (See id. at A-312, 315–16.) Second, replacement counsel
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`delayed bringing their trial issues before the court “up to 27 days from the time
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`they were aware of a problem” despite being retained less than 60 days before trial
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`was set to begin. (Id. at A-312, 315–16, 319–20.) Third, plaintiff’s counsel believed
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`Jackson may have an “ulterior motive” for discharging an attorney “who has
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`represented them successfully for 14 years, and in this case aggressively and
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`thoroughly and extremely competently” solely because of “high fees,” when
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`replacement counsel “has to start from ground zero and read the entire file” and
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`Attorney Raymond offered to help get replacement counsel prepared. (Id. at A-312–
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`13, 320–21.) Fourth, replacement counsel reason for requiring an adjournment
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`shifted,
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`including replacement counsel’s daughter’s graduation, Jackson’s
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`12
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`schedule, and the missing documents. (See id. at A-318–19.) Fifth, the outstanding
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`documents appeared to be attorney work product, which counsel described as “the
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`last thing I need … especially if Mr. Raymond has been fired… no disrespect….”
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`(Id. at A-319.)
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`The court next addressed the missing files and Reed Smith’s exercise of a
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`retainer lien. Attorney Gase stated that Jackson was “unhappy with [Raymond]
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`from the size of the bills” but did not say the termination was “for cause.” (Id. at
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`A-325–26, 339.) Judge Wooten summarized Jackson’s position on the retainer lien
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`issue as not a challenge to the validity of the retainer lien, but as a request to find
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`an exception “under the grounds of exigent circumstances.” (Id. at A-329–30.)
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`With respect to the documents that were turned over, Attorney Raymond
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`stated:
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`I have given them almost all the files. In fact, I have given him
`everything that we had when we started preparing for trial last
`December. They have all the pleadings, all the depositions, all the
`expert reports, all the documents produced by either side. Lots of
`correspondence. All sorts of research. They have all of that. The only
`thing that we haven’t given them, maybe a few miscellaneous things
`that fell through the cracks. The only thing is our actual trial
`preparation work product. Our proposed voir dire. Our outlines for
`witness testimony and things like that in the state that they were at the
`time that we were dismissed. So that’s all. Everything else they have
`to get ready for trial.
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`(See id. at A-331–32.) He also stated, “[A]ll that we’re asking the Court to do is to
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`direct them to post a bond in the amount of our fees. We will turn the files over to
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`them.” (Id. at A-332.) Attorney Raymond then requested a referral to binding
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`arbitration or a special master to have a third party resolve whether the fees were
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`reasonable. (See id.) After much discussion, the parties agreed, and the court
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`ordered an appeal bond in an amount under seal and a referral to a special referee.
`13
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`(See id. at A-335–37.) When prompted for comments, new counsel did not offer
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`any or otherwise object. (See id. at A-340.)
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`Ultimately, Judge Wooten denied both motions. With respect to replacement
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`counsel’s request for an adjournment, Judge Wooten described the painstaking
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`process by which a trial date was chosen, including to accommodate Jackson’s
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`busy schedule in 2015. (See id. at A-342–43.) Judge Wooten added:
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`“Notwithstanding that, the defendant chose to change counsel. That was his
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`choice. And I pointed out that it’s his choice because he did not discharge his
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`current counsel for any particular reason or for cause but for a financial
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`convenience. That is not reason enough for us to change the trial date.” Id. For
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`replacement counsel’s request to add a third-party action, the court denied the
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`motion on the grounds that it could be pursued separately, including after trial.
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`(See id. at A-343.)
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`iii. Discovery of Three Uncalled Witnesses
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`It is undisputed that neither Appellees nor replacement counsel ever
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`obtained discovery from the Three Uncalled Witnesses during the Leviston case.
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`During the bankruptcy action, the parties obtained discovery from Rick Ross and
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`the Internet Provider. Based on the record, it does not appear Murray was deposed
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`or provided documents.
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`Rick Ross signed an affidavit on April 13, 2020 and Jackson deposed him
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`nine days later. (See ECF 24-6 (Appeal Br. App. 6, A-1247-1504) at A-1387–95 (Rick
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`Ross Depo. Excerpt); ECF 24-7 (Appeal Br. App. 7, A-1505–1774) at 1587–1629 (Rick
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`Ross Dep. Excerpt); AP ECF 302-17 (Mot. Summ. J. Ex. 17, Ross Aff.).) Rick Ross
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`Case 3:21-cv-00911-VLB Document 36 Filed 06/30/23 Page 15 of 56
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`stated that he became aware of the Video in 2009 during a radio interview with “Big
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`Tigger.” (AP ECF 302-17 ¶ 9.) In his deposition, he claimed that he did not address
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`the Video directly but instead “redirect[ed] the conversation” to promote his latest
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`album, Deeper Than Rap, “by suggesting that I would post the video on
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`‘DeeperThanRap.com’, a website I created to advertise my new release.” (Id.; ECF
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`24-6 at A-1606.) He denied posting or authorizing anyone to post the Video on any
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`website. (See id. ¶ 10.) He also denied ever possessing the Video. (See id.) When
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`asked if he ever owned or controlled “ThisisSabrinasSin.Ning.com,” Rick Ross did
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`not recall. (ECF 24-7 at A-1592, 1596–99 (Rick Ross Depo Excerpt); AP ECF 302-17
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`¶ 16.) With respect to Jackson’s claims against Reed Smith, Rick Ross stated he
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`would have refused to be interviewed by Jackson’s lawyers and, if subpoenaed,
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`would have testified that he never possessed or posted the Video. (AP ECF 302-17
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`¶¶ 13–14.)
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`Jackson served a subpoena duces tecum on the Internet Provider in 2019,
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`requesting information from January 1 through April 30 of 2019. (AP ECF 335-43
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`(Mot. Summ. J. Opp’n Ex. 43, NING Ltr.).) The Internet Provider informed Jackson
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`that the company had a policy of permanently deleting information when there is
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`an outstanding balance lasting more than 60 days. (See id.) The only information
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`the Internet Provider retained was ThisisSabrinasSin.Ning.com’s creation date of
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`February 26, 2009 and deletion date of April 4, 2012. (See id.) The Internet Provider
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`also stated that it had never been served with a subpoena.
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`While Jackson never deposed or obtained documents from Murray, he
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`testified about their conversation concerning the Video. Jackson testified that
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`Case 3:21-cv-00911-VLB Document 36 Filed 06/30/23 Page 16 of 56
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`Murray approached him about disseminating the Video and stated he hoped to get
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`a book deal. (AP ECF 335-3 (Summ. J. Opp’n Ex. 2, Jackson Dep.) at 10:23–11:25.)
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`With respect to Murray communicating Leviston’s purported consent, Jackson
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`testified, “And [Murray] was like, Nah, she don’t care. Like, let’s just put it out there
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`anyway and see if possibly we could do a book or something else after that comes
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`from it.” (Id. at 11:21-25.)
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`iv. Jackson’s Standard of Care Expert
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`Jackson retained Attorney Jonathan D. Lupkin as his expert on the attorney
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`standard of care. Attorney Lupkin is a practicing attorney with 26 years of
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`experience, including litigating legal malpractice, professional liability, and IIED
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`claims. (AP ECF 335-29 (Summ. J. Opp’n Ex. 28, Lupkin Report) at 1.) Attorney
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`Lupkin stated four appendices were attached to the report: Appendix A, a list of
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`pending litigation with which he is involved; Appendix B, a list of his presentations
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`and seminars; Appendix C, a list of documents on which he relied in forming his
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`opinions; and Appendix D, a Statement of Assumed Facts that he was provided.
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`These appendices were not filed on the docket.
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`a. Defense Strategy
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`Attorney Lupkin described Appellees’ defense strategy as containing four
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`principals. First, “to defeat Ms. Leviston’s claim for violations of §§ 50 and 51 of
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`the New York Civil Rights Law, Reed Smith intended to argue that Mr. Jackson’s
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`use of Ms. Leviston’s likeness was not for commercial purposes—an essential
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`element of a claim under those statutes”—because BooBooTV did not provide
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`Jackson advertising revenue. (AP ECF 302-43 at 14.) Second, “to defeat Ms.
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`Case 3:21-cv-00911-VLB Document 36 Filed 06/30/23 Page 17 of 56
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`Leviston's IIED claim and/or mitigate any award of damages, Reed Smith intended
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`to argue that Mr. Jackson acted without a culpable state of mind.” (Id.) Namely,
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`Reed Smith would have Jackson testify that Murray told him Leviston consented
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`to publishing the Video. (See id.) Third, “to mitigate Ms. Leviston’s compensatory
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`damages, Reed Smith intended to argue that she did not suffer substantial
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`emotional trauma from the posting of the Video because she worked in the “sex
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`trade” and was thus comfortable with-and would perhaps benefit from—that kind
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`of exposure.” (Id. at 14–15.) Fourth, “to deflect blame from Mr. Jackson in the
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`hopes of reducing punitive damages, Reed Smith intended to argue that the impact
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`on Ms. Leviston of Mr. Jackson’s publishing of the Video was mitigated by Mr.
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`Ross’s earlier publication of the Video.” (Id. at 15.) Reed Smith would elicit this
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`testimony through Jackson and two of his employees who were involved in
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`creating the Video and BooBooTV. (See id.)
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`b. Standard of Care
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`Attorney Lupkin stated New York Rule of Professional Conduct 1.3(a) sets
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`the applicable standard of care—to “act with reasonable diligence and promptness
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`in representing a client.” He stated that “failure to investigate may fall below the
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`standards of ordinary and reasonable skill.” (AP ECF 302-43 at 16 (citing cases).)
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`c. Opinions
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`Attorney Lupkin concluded Appellees’ failure to adequately pursue evidence
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`from the Three Uncalled Witnesses fell below the standard of care. With respect to
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`Ross and the Internet Provider, Attorney Lupkin stated he believed these witnesses
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`would have had evidence relevant to Ross’ control over the SabrinaSin website.
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`Case 3:21-cv-00911-VLB Document 36 Filed 06/30/23 Page 18 of 56
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`(AP ECF 302-43 at 22, 26.) As for Murray, Attorney Lupkin opined that “relying
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`solely on the self-serving testimony of a party witness is suboptimal” and that
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`Murray’s testimony would have lent credibility to Jackson. (Id. at 29.) He also
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`expressed concern that Jackson’s testimony would have been inadmissible
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`hearsay and concluded, “nothing prevented Reed Smith from asking Mr. Murray
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`what he would say before deciding whether to elicit his testimony.” (Id. at 30.) In
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`drawing these opinions, Attorney Lupkin discussed deposition testimony from
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`Attorney Raymond, Attorney Farber, Singh, and Villemeur; subpoenas Reed Smith
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`drafted but did not send; e-mail correspondence between Reed Smith attorneys;
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`reflections from mock jurors who participated in a jury consultant’s 2015 mock
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`trial; and he cited additional evidence. (See id., generally.)
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`3. Summary Judgment
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`Appellees moved for summary judgment on April 30, 2020. (AP ECF 300
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`(Mot. Summ. J.).) In relevant part, they argued they were not negligent as a matter
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`of law for two reasons. First, according to the common law “attorney judgment
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`rule,” they did not breach their duty of care because they chose a reasonable trial
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`strategy, even though it was a strategy that Jackson did not prefer. (Id. at 19–23.)
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`Second, assuming Appellees breached their duty, the record does not establish
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`their breach proximately ca