The Oakley v. MSG War Continues

Feb 21, 2025

By Jeff Birren, Senior Writer

Charles Oakley and James Dolan are classic “don’t invite ‘ems.” Oakley once played for the New York Knicks. The Dolan family owns Madison Square Garden (“MSG”), and Dolan is its CEO. MSG owns the Knicks and Rangers, and Dolan is the CEO/operator of both teams. On February 8, 2017, Oakley intended to see a Knicks game at MSG, but it was not to be. Instead, he was ejected and arrested. NBA Commissioner Adam Silver called the situation “beyond disheartening” (NBA Communications, Official Release (2-17-2017). Oakley later sued Dolan and MSG for the manner in which he was treated. Recently, both sides sought protective orders. Dolan fought to be absolved from sitting through a deposition as befitting an “apex witness.” The Court gave each side something and sent the parties back to discovery. Oakley v. MSG Networks, Inc., S.D. N.Y., Case No. 17-cv-6903 (RJS) (11-21-2024).

Some Background

Dolan’s father, Charles Dolan, was the prime force behind Cablevision. Along the way, Cablevision acquired numerous assets, including MSG. The Dolan family later sold Cablevision while retaining MSG. Born to wealth, James Dolan has been described as having “a volcanic temper and a born-on-third-base makeup, and as a hapless owner.” Early on it was “his alcoholism and his abuse of cocaine and pot that forced him into treatment at the Hazelden clinic” (“James Dolan, Unplugged,” Ian O’Connor, ESPN (12-17-18).

            Oakley played in the NBA from 1985 through 2004, including with the Knicks from 1988 to 1998. He was known for his rebounding and defensive prowess. His behavior at the Knicks-Clippers game on February 8, 2017, certainly attracted attention. He was approached by security guards and informed that his presence was no longer an option. Oakley objected and seemingly placed his hands on one of the guards. He was escorted out of MSG and arrested. Criminal charges were filed, and Oakley entered into a plea deal. He was not happy.

Oakley filed a lawsuit on September 12, 2017 against Dolan and MSG. Oakley is represented by Wigdor, LLP., and Petrillo Klein & Boxer, LLP. Douglas Widor is represented by the Law Offices of Steven Ross. (Surely there is a story there.) Meanwhile, Dolan doubled up. In his “individual capacity” Dolan is represented by Walden Macht Haran & Williams; Gibson, Dunn & Crutcher; and King & Spaulding. In his “professional capacity” Dolan added Ropes & Gray. The same cast represent MSG Networks, Inc, MSG Garden Company, and MSG Sports & Entertainment, LLC.

Limited Case History

When the District Court ruled on the dueling discovery motions, it stated: “[t]he Court assumes the parties’ familiarity with the factual background and procedural history of this case as summarized in the September 10 Order. (See Doc. No. 181 at 2-3).” The following summarizes that Order. After Oakley sued both Dolan and MSG, the defendants filed a motion to dismiss the claims. The District Court granted the motion on February 19, 2019, (Doc. No. 68). The Second Circuit affirmed the Court’s ruling with respect to all but Oakley’s assault and battery claims. Oakley v. Dolan, 833 F. App’x 896, 902 (2d Cir. 2020); Oakley v. Dolan, 980 F.3d 279, 284 (2d Cir. 2020).

            Back in the District Court, the parties resumed their wranglings. Oakley sought to file a second amended complaint in an effort to add new claims. (Doc. 106). The defendants moved for summary judgment. (Doc. 102). The Court granted the motion in favor of the defendants and denied Oakley’s motion as futile. (Doc 212). The Second Circuit “vacated the Court’s grant of summary judgment and remanded the case for, among other things, reconsideration of Oakley’s motion to amend.” See Oakley v. Dolan, No. 21-2939, 2023 WL 3263618, at *3 (2d Cir. May 5, 2023).

            The District Court granted Oakley’s motion to file an amended complaint against MSG that “alleged new facts” in support of the claims against the MSG defendants, but denied the motion insofar as it sought to add Dolan as a defendant, since “an amendment adding a new defendant without substituting a previous, improperly named defendant does not relate back under” Rule 15(c)(1)(C), making new claims against Dolan time-barred. (Doc. No. 158.) MSG answered the amended Complaint on May 2, 2024 (Doc 166).

The “parties commenced discovery on the only remaining claims in the case: Oakley’s assault and battery claims against the MSG defendants.” The September 10, 2024 Order was based on Dolan’s insistence that Oakley “has failed to meet his burden to show that Mr. Dolan has unique knowledge that other witnesses are incapable of conveying.” The Court told Dolan that he “misunderstand[s] which party bears the burden here. It is the defendants who must show that Dolan ‘has nothing to contribute’ to this litigation.” (Order, at 5, (emphasis in the original)). The Court spent a page and a half explaining why this was not true. “At the most basic level, Dolan was an eyewitness to the removal of Oakley and can provide personal observations as to Oakley’s behavior that evening and the force used to remove him.” Therefore, MSG’s efforts to shield Dolan were denied.

November 20, 2024, Discovery Ruling

The Court was confronted with four discovery disputes. MSG filed a motion for reconsideration, asking the Court to change its mind and relieve Dolan of the obligation from being deposed. Alternatively, Dolan desired an order that the scope of the deposition be limited, and that if he had to be deposed, it should occur “after the depositions of all other MSG employees have been concluded.” Oakley moved to maintain the redactions on exhibits “that MSG submitted.” MSG and the non-party NBA moved to maintain redactions in exhibits submitted by Oakley.

Motion For Reconsideration

            The “standard” for granting reconsideration “is strict, and reconsideration will generally be denied unless the moving party can point to controlling decision or data that the court overlooked.” A “motion for reconsideration ‘is not a vehicle for relitigating old issues presenting the case under new theories, securing a rehearing on the merits, or otherwise taking a second bite at the apple. Analytical Survs., Inc. v. Tonga Partners, L.P. 684 F.3d 36, 52 (2nd Cir. 2012).’”  The earlier referenced motion insisted that Dolan was not a necessary witness to the reasonableness of force used against Oakley. MSG again sought to protect Dolan as an “apex witness, and that “newly discovered evidence suggests that the deposition is intended to harass Dolan.” However, the Court found that none of this “met the ‘strict’ standard” for reconsideration.

  1. Relevance

Dolan’s counsel presented “no new legal authority and instead selectively quoted from” a prior Order, but, as pointed out, the same paragraph “explained that Oakley’s allegation concerning Dolan’s hand gestures” could support Oakley’s inference that Dolan “instructed or encouraged the use …of excessive force.” There was no inconsistency between the two orders, and the prior order “was based on the untimeliness of Oakley’s request,” not on relevance grounds. The Court never held, or even suggested, that Dolan did not have relevant knowledge and could not be deposed.

            The Court gave Dolan’s army of attorneys a lesson in civil procedure. “After all, it is a fundamental principle that ‘[e]vidence is relevant if (a) it has any tendencyto make a fact more or less probable that it would be without the evidence, and (b) the fact is of consequence in determining the action. Fed. R. Evid. 401). It is-well-established that the ‘basic standard of relevance … is a liberal one,’ Daubert v. Merrell Dow Pharms., Inc., 509 U. S. 579, 587, 223 S. Ct. 2786.” It “imposes a low bar… in a discovery dispute.” Dolan’s lawyers knew the law long before filing the motion.

            Oakley was “entitled to depose Dolan regarding the instructions he gave to MSG security guards on the evening of the incident” There are multiple ways to interpret the events that transpired. Which side was the aggressor? Which party used greater force than necessary? If “Dolan instructed the security guards to use force against Oakley regardless of Oakley’s behavior” that would “undermine the allegation that Oakley instigated the altercation.” Finally, if Dolan did so instruct the security guards, that possibly could lead to punitive damages. The Court did not rule that it had made an error in allowing Dolan to be deposed.

  1. “Apex-Witness Doctrine”

Dolan is the apex of the MSG world, but that does not excuse him from complying with elementary civil procedure. His array of lawyers “provides no controlling decisions that the Court overlooked.” Instead, its argument “mischaracterizes the Court’s prior ruling, which was not based on Dolan’s ‘generalized knowledge of the incident in question,’ as MSG claims.” Dolan was present that night. He saw the incident and was “alleged to have witnessed Oakley’s belligerent behavior.” The cited case had no application as Dolan “had a courtside seat to the action” and “is alleged to have been a participant in the conduct at issue.” This concept “is plainly inapplicable here.” 

  1. Harassment Concerns.

MSG insisted that there was “newly discovered evidence” to substantiate the notion that Oakley sought to depose “Dolan simply to harass him.” Two of the offered exhibits were publicly available newspaper articles that predated the discovery dispute. Because these articles “could have been found by due diligence prior to the Court’s ruling, the Court may not consider them on a motion for reconsideration. Space Hunters, Inc. v. United States, 500 F. App’x 76, 81 (2nd Cir. 2012).”

            The next several exhibits were emails sent to Oakley that encouraged him to go after Dolan. MSG failed to offer any “evidence to suggest that Oakley responded to or endorsed these messages. Nor do the messages, which all date from months before the present discovery dispute, indicate that Oakley’s intent in deposing Dolan was solely to harass him.” Lastly, MSG pointed to statements of one of Oakley’s counsel gave to the New York Post that he looked forward to deposing Dolan. The Court stated one of these statements “was an accurate characterization of the September 10 Order” and the other “merely reflects” a “belief that deposing Dolan will be beneficial to Oakley’s case.” This material, according to the Court, “does not resemble the circumstances” that led to protective orders to prevent harassment. As a result, the Court denied the motion for reconsideration.

Motion for Protective Order

MSG also filed a motion for protective order as an “alternative” argument, made “for the first time.” It sought to limit the topics that could be addressed at Dolan’s deposition, appoint a special master to oversee the deposition, and have Dolan be deposed only after all of the other MSG employees were deposed. Dolan “carries the burden of proof to show that good cause exists” for such an order. Fed. R. Civ. Pro. 26(c) requires “a particular and specific demonstration of fact, as distinguished from stereotyped and conclusory statements.” This requirement was missing. The Court expected Oakley’s counsel to “comply with their ethical obligations,” and Dolan was free to return to court if the deposition violates “permitted conduct.” (Fed. R. Civ. P. 30(d)(3)(A)).

            The sequence of depositions “is at the discretion of the trial judge.” Courts “have routinely ordered that CEOs and corporate officers be deposed after other employees.” The depositions of MSG personnel will “narrow the scope” of Dolan’s deposition. The Court was “unmoved” by the request to appoint a special master, “which the Court regards as an unwarranted extravagance to which the parties are not entitled.” The Court expected counsel to behave consistent with the rules, and “will have little patience for lawyers who use the discovery process as a sport for purposes unrelated to the development of evidence.”

To Seal or Not to Seal

Both parties, and the NBA, filed motions to seal records previously submitted to the Court. Judge Richard Sullivan quoted the Second Circuit: “[t]he common law right of public access to judicial documents is firmly rooted in our nation’s history. Lugosch v. Pyramid Co. of Onondaga, 435 F.3d 110, 110 (2nd Cir. 2006.)” There is a “presumption of access” to judicial documents, but that begs the question of what is a “judicial document.” It is a “document that has been placed before the court by the parties” and is both “relevant to the performance of judicial duties” and “useful in the judicial process. Mirliss v. Greer, 952 F.3d 51, 59 (2nd Cir. 2020.)” Once that is established, the court must determine the weight of the presumption, and balance the factors that disfavor disclosure, such as the “privacy interests of those resisting disclosure.”

MSG filed eight exhibits in its motion for reconsideration. Three contain redacted material. Oakley moved to maintain those redactions, including telephone numbers and irrelevant messages, according to Oakley. The Court viewed the unredacted exhibits and agreed “that the redactions obscure personal identifiable information as well as brief references to a private” matter that had “no bearing on any material issues in dispute in this case.” The records were “judicial documents,” but Oakley’s “privacy interests” as well of those he corresponded with “via text” outweighed the usual presumption for open access. The Court granted Oakley’s motion to maintain the redactions.

In opposing MSG’s reconsideration motion to preclude Dolan’s deposition, Oakley submitted a letter that included quotations from two NBA security guards. They indicated that Dolan ordered Oakley to be removed from MSG. Oakley originally filed a sealed version of the document but then sought to file an unredacted version. Both MSG and the NBA opposed public access to Oakley’s letter that was based on the NBA reports.

            This was “clearly a judicial document… Therefore, the presumption of public access applies, and the burden falls on MSG and the NBA to overcome that presumption.” MSG argued that Oakley was using the material “as a vehicle to disparage MSG, the NBA, and Mr. Dolan, including in the tabloid press.” The Court noted that Oakley included two quotes to “refute MSG’s repeated assertions that Dolan did not order Oakley’s removal.” Supposedly, Dolan was merely “one of thousands of eyewitnesses to the events” and should therefore not suffer the indignity of being deposed, although he had the unchallenged power to have Oakley removed. The two lines were relevant to determine resolution of MSG’s motion for reconsideration. They “are therefore material to ‘the exercise of Article III judicial power’ and of value to those monitoring the federal courts. Mirliss, 952, F.3d at 59.”

            MSG and the NBA tried another approach. Releasing these reports “may make witnesses ‘reluctant to supply statements to the NBA during investigations.’” The Court “is not persuaded that publicly filing the two sentences … which simply relay the preliminary fact findings of the NBA will chill” future NBA investigations. However, the Court redacted the names of the two individuals involved in making that report. They were not affiliated with any party, were not accused of any wrongdoing, and did not ask to be involved in the litigation. Their privacy interests outweighed the presumption of public access “at this stage of the litigation.”

            In the end, Dolan had to submit to a deposition, but only after his employees were deposed. Oakley’s personal records remained sealed. Oakley’s letter quoting the NBA’s preliminary findings that contradicted Dolan were to become part of the public record, though the names of the NBA’s investigator were to remain sealed for the timing being. Everybody wins something, everybody losses something, and lawyers profit.

But It Ain’t Over

The pretrial skirmishes continued. This is merely one of 24 Orders in this case from November 1, 2024, through February 10, 2025. Oakley sought to depose former head of MSG security, Frank Benedetto. Benedetto was fired the day after the game. Benedetto resisted, sought to limit the scope of the deposition, and opposed producing documents unrelated to the game in question. The Court ordered Benedetto to appear for a deposition, but limited the questioning to the specific game, and, because Benedetto had produced documents related to the game, nothing else would require production. (Order, 1-15-2025). Oakley then filed a motion for clarification or reconsideration. It was denied. (Order, 1-27-2025). MSG’s reasons for terminating Benedetto were off-limits.

That same day, MSG sought to change the location of Dolan’s deposition in a highly redacted letter. Counsel asserted it would be “irresponsible from a security standpoint to expose this prominent CEO to an unfamiliar” location as Dolan “is a prominent figure.” If the deposition had to go forward, Dolan’s security squad should first sweep the room and then be present during the entire deposition. Counsel also went back to the well to complain about possible irrelevant questions, supposedly because Oakley had just produced articles concerning public comments Dolan made about other people. MSG’s counsel opined that it had been “eminently reasonable.” It requested that Dolan’s deposition take place at MSG’s office and threatened that if Oakley’s counsel strayed from the allowed topics, it would “promptly ‘move to terminate the deposition.’” Oakley opposed this attempt to disrupt this last effort to disrupt the deposition.

The Court rejected the request the same day at the bottom of the letter. “The law in this district is clear: [T]he party noticing the deposition usually has the right to choose the location. Viera v. United States, No. 18-cv-9270 (KHP), 2019 WL 6683556, at *2 (S.D.N.Y. Dec. 6, 2019) (internal quotation marks omitted).” No good cause was shown to alter the location or procedures. (Order, 1-27-2025).

The deposition apparently went forward, presumably without dire incident, because Oakley sought to reopen the deposition. That was denied. (Order, 2-7-2025).

Editorial

Oakley was an excellent NBA player, including his years with the Knicks. Whatever he did that night, the public now knows that the NBA’s preliminary report indicated that Dolan ordered Oakley to be removed from MSG. MSG counsel knows the law. Consequently, the near hysteria concerning the deposition must come from elsewhere. Dolan retains his “apex” birthright, but for all of the legal resources he committed to avoiding being deposed, the Federal Rules of Civil Procedure thwarted his desire. It is a tale for tabloids. Dollars do not mean sense, but money may buy motions.

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