Kessler v. Yates: Antitrust Rivals Reshaping Business of Sports

At the intersection of sports and law, Jeffrey Kessler is considered the GOAT.

The Michael Jordan of antitrust agitators, perhaps, or the Tom Brady: Kessler has represented both.

A longtime partner with Winston & Strawn LLP, Kessler, 71, has battled a handful of top lawyers throughout his career. But in recent years a consistent counterweight in defending the sports establishment has emerged in Chris Yates, a partner at Latham & Watkins LLP.

They’re facing off in federal court over a dispute against NASCAR, which is being sued over monopolization claims by Jordan’s 23XI Racing team, and another team, Front Row Motorsports Inc., both of which are represented by Kessler. A trial is set for December.

The two were part of a deal announced in July where top US swimmers—represented by Kessler—settled claims challenging World Aquatics—represented by Yates—over its control of international swimming competitions.

“I know some of the tactics and strategies he likes to employ; I’m sure he knows some of the tactics and strategies I’ve employed,” Kessler said of Yates. “It makes it more of a game of three-dimensional chess for both of us.”

Kessler’s sports client list is legion: He handled cases that opened the door for National Football League free agency, equal pay for the US women’s soccer team, and college athletes receiving name, image, and likeness payments.  He also represented Brady, then the New England Patriots quarterback, in the “Deflategate” case against the NFL.

Yates, 58, has defended sports clients including Ultimate Fighting Championship, sports retailer Fanatics, and, in numerous suits, US Soccer. Earlier this year, a jury cleared the organization of claims brought by a former soccer league, North American Soccer League, represented by Kessler.

“We’re both competitive,” Yates said of his relationship with Kessler. “And we both want to deliver great results for our clients.”

Antitrust Crosshairs

Sports and antitrust have a long history in this country, including the Supreme Court decision in 1922 that exempted Major League Baseball from the Sherman Antitrust Act.

In NCAA v. Alston—where Kessler argued for the plaintiffs—the Supreme Court in 2021 found the compensation rules for college athletes amounted to a violation of antitrust law, opening the door to NIL payments.

The decision was like a “dam breaking” for collegiate athletics, said Stephen Ross, a law professor at Penn State and co-director for the school’s Center for the Study of Sports in Society.

In June, Kessler and Yates helped secure the landmark $2.8 billion settlement among the NCAA, athletic conferences, and student-athletes that for the first time allows colleges to pay athletes directly.

Ross expects antitrust cases to continue to redefine the sports landscape. 

“The key to antitrust suits is market power,” Ross said. “Once a league becomes successful and has some ardent followers, they have market power.”

‘Build Up An Expertise’

In 1977, when Kessler began as an associate in Weil Gotshal & Manges LLP’s antitrust department, “no one would have said to anybody in law school, ‘Do you want to be a sports lawyer?” Kessler said. “The business was much, much, much smaller.”

He built his practice over time, representing plaintiffs including former New York Jets running back Freeman McNeil, who sued the NFL, saying it restrained players from moving to other teams. That claim led to the first NFL free agency in 1993.

Yates was part of the Latham team that in 2004 successfully defended Oracle Corp.  at trial in the Justice Department’s suit seeking to block the company’s acquisition of rival PeopleSoft Inc. He was flying all over the country, deposing key third-party witnesses, and watching great trial lawyers in action.

“That was a really formative experience,” Yates said. “I’d worked on lots of antitrust cases before then, but it was just so intense, so fast.” 

Yates had a traditional antitrust practice representing Bay Area tech companies. He then had an opportunity to represent US Soccer in an antitrust suit where a judge eventually granted the soccer organization’s motion for summary judgment.

“US Soccer began coming back to me and then other sports clients just started coming to me over the years,” Yates said. “You sort of build up an expertise and a reputation and then you find yourself in more and more different cases.”

Defining Markets

Kessler is quick to challenge alleged conspiracies as unreasonable restraints on trade. Yates goes after antitrust plaintiffs’ market definition, which is designed to demonstrate that a defendant wields power.

That was an important defense in cases like the one NASL brought against US Soccer, which won on that threshold issue.

“What we see are plaintiffs trying to really narrowly define markets,” Yates said. 

Yates said many class actions are being used today to effectuate change that historically would be achieved through “individual litigation or individual conversations between an athlete and a sports organization.”

Yates often argues against class certification because plaintiffs sometimes try to “shoehorn” issues that aren’t common across all athletes, he said.

For Kessler, it’s long been about pushing back against powerful sports organizations’ effect on athletes.

“When I first started out, the athletes didn’t have many resources,” Kessler said. Today, many athletes are very well compensated, “but we are still fighting for economic justice and fairness.”

Jordan v. Ewing?

The complexity of antitrust law makes specialization important, said Christine Bartholomew, professor at University at Buffalo School of Law who focuses on antitrust law.

“You see a lot of the same players,” Bartholomew said. “You really do need people who understand the economic consequences, the particularized rules. There’s a lot of money at stake.”

The sports antitrust world is “a small one,” said Rakesh Kilaru, partner with Wilkinson Stekloff LLP, who represents the NCAA and worked in tandem with both men in support of the sports organization’s $2.8 billion antitrust deal with athlete-plaintiffs that gained final approval in June.

“Folks who have shown that they handle those cases at a high level, like Chris and Jeffrey, are going to be in demand,” Kilaru said.

They’re mutually complimentary. Kessler said he’d rather litigate against a tough competitor like Yates, “than against someone who doesn’t know what they are doing.”

Yates says: “Going up against a really terrific lawyer like Jeffrey is in some ways easier because you kind of cut to the chase on a lot of things.”

But their competition has been compared to Michael Jordan’s basketball court clashes with fellow Hall of Famer Patrick Ewing.

Jordan himself made that comparison, Kessler said during an interview with Bloomberg Law in the lawyer’s Manhattan offices. (Jordan was unavailable for comment through a spokeswoman.)

Jordan and Ewing “have such tremendous respect for each other, and they would frequently end up playing in the playoffs against each other and would try to anticipate each other’s moves,” Kessler said of Jordan’s time with the Chicago Bulls, and Ewing’s with the New York Knicks. 

“But they’re also competitors, so it’s not like they are best of friends outside of that,” Kessler recounts. “You also have to keep a certain amount of distance in terms of that because you are competing so fiercely against each other.”

Legal Origins

Kessler grew up in Brooklyn, the first person in his immediate family to go to college.

Yates was born in Africa to an American mother who served in the Peace Corps in Nigeria, and an English father, a civil engineer who helped supervise the building of dams and other infrastructure projects.

Both attended Columbia Law School but didn’t overlap.

Yates joined Latham in 2003 and served as co-chair of the firm’s antitrust practice from 2010 to 2020.

Kessler left Weil in 2003 to become litigation co-chair at Dewey Ballantine, which merged with LeBoeuf, Lamb, Greene & MacRae. He joined Winston & Strawn in 2012, after the merged firm, Dewey & LeBoeuf, announced it was going to cease operations, and he brought with him more than 60 attorneys and their support staff.

Yates says his goal before a jury is to take “a really complicated area of the law and put it in a way that is digestible and understandable for lay people.” 

At the US Soccer trial earlier this year, he told the jury the NASL “never put in the work” to meet standards for a top-tier designation.

Yates brings a “combination of intellect and thoughtfulness and good judgment,” said Brad Ruskin, co-chair of the sports law group at Proskauer Rose LLP and lead attorney for Major League Soccer, which also was sued by the NASL as part of the same case. “He is very good at keeping calm even at the tensest moments.”

For Kessler, preparing can mean hours simulating arguments in moot court, a strategy he used in the Alston case.

During the US Soccer trial, Kessler “had notes, but he only looked at them as a reference point,” recalls Clifford H. Pearson, partner with Pearson Warshaw LLP, which also represented NASL in the case.

“I think win, lose, or draw, it really was an amazing performance,” Pearson said. “It was Perry Mason-ish, if there is such a word.”

Team Sports

Kessler and Yates both note that high-level law involves a lot of people.

“I view this as not just me; it’s the team,” Yates said. “Litigation and trials are team sports.”

Says Kessler: “The only reason I can handle so many different cases at once is because I’ve got these incredible teams at every level.” 

The men say they don’t keep score. But they have a trial—the NASCAR case—coming up in short order, and possibly more in the future.

Many antitrust cases end up in compromise, and having lawyers familiar with antitrust settlement negotiations is an advantage for all involved, Ross said.

“You need to respect the people that you go up against,” Yates agrees. “Because they may be working on the same side as you in a month, in a year, in two years.”