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By Jordan Sigler
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Near a mountain in Kyoto, Japan, Andrew Kessler was enjoying a vacation in Japan in the summer of 2024 while trying to nail down the final details of a contract extension for Green Bay Packers quarterback Jordan Love.
Following a phone call that would make Love at that time tied as the highest-paid player in NFL history on a four-year deal worth $220 million (with a record-setting $75 million signing bonus). Jeffrey Kessler remembers his son running up the mountain to give his family news of the completed deal.
Family and sports are interchangeable for the Kessler family, and Andrew and Jeffrey have had some notable exchanges during their own remarkable careers.
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Jeffrey is one of the most well-known attorneys in sports and is a partner and co-executive chairman of Winston & Strawn. Andrew is an NFL player agent at Athletes First, which Forbes named as the No. 1 most valuable football agency in 2025.
Jeffrey has represented the NFL Players Association since 1989. His work with the NFLPA created an interesting dynamic for the league in 2006 when Andrew, working under Tom Condon, came up with the idea for a "poison pill" contract that would allow future Hall of Fame offensive guard Steve Hutchinson, then under the transition tag, to sign a contract with the Minnesota Vikings.
Andrew put a clause in the contract, viewed as a principal term (meaning that it had to be matched), that if Hutchinson were to play two or more regular season games in the state of Washington, the entire seven-year contract would be guaranteed. Since Minnesota plays outside of the Seahawks division, the Vikings would never have to worry about that clause going into effect.
Seattle couldn't agree to match the deal with the Vikings, but they challenged the contract, arguing that the clause should not qualify as a principal term.
Based on Andrew's reading of the Collective Bargaining Agreement at the time (the CBA has since changed to exclude the "poison pill" in exchange for other benefits for players), he believed the clause should qualify as a principal term. Jeffrey defended the case after working with Andrew, and they won.
"I was working with Andrew, talking about the strategy and learning about what they did and defending the player and making the arguments," Jeffrey said. "So we were very much sort of on the team together. As I said, Andrew was coming up with clever ideas to create new player benefits, which I could then go out and defend for the unit."
Those talks on sports and legal matters can breach into family life. Andrew and Jeffrey try to keep their family abreast in what's going on in their careers. Like with Andrew during the Japan vacation, work can spill over into more intimate parts of their lives.
In 2011, Andrew's son, Jordan, was born a month early. Jeffrey, representing the National Basketball Players Association amid a lockout, rushed to meet his grandson.
"I was actually holding him at one point as a newborn baby, talking on a phone call to the NBA to settle the 2011 NBA lockout," Jeffrey said. "So Jordan Kessler was a baby party to the settlement of that lockout because I couldn't be there in person."
Andrew has helped to recruit some of Jeffrey's biggest wins against the NFL and NCAA. In 2011, Jeffrey needed an incoming rookie to challenge the lockout in Brady et al. v. the National Football League et al. Jeffrey needed a player who would be a first-round pick, because Day 2 or Day 3 prospects would be worried that they could fall in the draft if they joined the suit.
Von Miller, then a star linebacker out of Texas A&M, represented by Athletes First, was the perfect candidate for the job.
"When my dad said, 'This is who we need. We need someone like so good that there could be like no backlash.' I told him, I said, 'Dad, I just watched on the field like the single most athletic pass rusher I've ever seen in my life,'" Andrew said of Miller.
"He was doing a drill against an offensive tackle who was a first-round pick in the same draft and a really good NFL player. He was a first-round pick in the draft and became a really good player. And he was making that tackle look like a high school player... It was nuts because they weren't in pads. They were on air."
Miller didn't face backlash from league owners for joining the suit. The Denver Broncos selected him with the No. 2 pick, with some general managers appreciating Miller's confidence and bravery to join the suit.
Carolina Panthers running back Chuba Hubbard, one of Andrew's clients at Athletes First, was a named plaintiff in the case Hubbard v. NCAA, which helped to collect and affect the damages that were established in NCAA v. Alston.
Another client of Andrew's at Athletes First, Buffalo Bills defensive tackle DeWayne Carter, was a named plaintiff in Carter v. NCAA, which was filed to expand the scope of House v. NCAA (which allowed for schools to pay athletes directly). The Carter and the House cases were merged for a $2.8 billion settlement.
Chicago Bears rookie quarterback Miller Moss, a client of Andrew's, volunteered to be a class representative for the injunctive relief settlement for House v. NCAA.
Players named in the above cases signed up mostly for unselfish reasons to help future college players earn benefits.
"Named plaintiffs, going back to Von Miller, Chuba, DeWayne Carter, Miller (Moss), like there's really nothing in it for them aside from helping the group," Andrew said. "Like there's not like a lot of extra benefits or things like that... These are pretty selfless acts, which guys are doing to help the whole body of players.
"Because they're going to get basically the same benefits from it either way. And again, the guys in college, these are really to help future college players because they're long gone from college. And yes, there's a settlement fund, but like what they get out of that fund is going to be similar either way."
Named class representatives receive small bonuses called "service awards" of approximately $10,000, but that's a tiny fraction of what those athletes will make on their first contract in the NFL.
Jeffrey was inspired to enter law because of his affinity for player activists. It was only fortuitous that he started his career interning and then working for Weil, Gotshal & Manges, which had the NBPA as a client. (He joined when the firm was settling a case Robertson v. National Basketball Association.) Jeffrey's work at the firm set him down a path of representing player unions and athletes.
"My social philosophy, in that even though I didn't plan it, because when I grew up in the '60s, one of the reasons I got interested in being a lawyer was because of player activists like Muhammad Ali and Bill Russell and the Olympic athletes who did their Black Power fists," Jeffrey said.
"Those were all things that sort of got me interested in the legal system, and so when this all came together, almost by accident... (It) is very natural for me to gravitate towards the players because I really thought that they were economically exploited, which they were, and so it became a good use of antitrust laws to try to help them."
Andrew took a different path from trial law, choosing to become a sports agent. When he realized being an athlete wasn't in his future, Andrew knew he wanted to work in sports. He was inspired by Jeffrey to work on the athlete's side of the bargaining table after witnessing his father and Jeffrey's partner, Jim Quinn, work on McNeil v. The NFL in 1992, which brought free agency to the league.
"I got to spend a good amount of time both at the beginning and then somewhat near the end of the trial there with him, watching him do witnesses, watching his longtime partner Jim Quinn cross-examine people," Andrew said. "Got to spend a ton of time with Gene Upshaw, obviously the head of the (NFL)PA at the time, and other players who were witnesses and named plaintiffs.
"That was kind of the first time I got to really hang out and be around players. I was only turning 12 years old, but I took it really seriously. I was really interested. I paid close attention."
Like Jeffrey, Andrew started working on the basketball side of things before venturing into football, interning at the NBPA during the summers of 1998 and 1999. Jeffrey introduced Andrew to NBA agent Marc Fleisher. Andrew knocked it out of the park in an interview, and he began interning for Fleisher, his first chance to work in the agent world.
The world Andrew was starting his career in was much different than the one Jeffrey saw in the 1960s, where athletes were being economically exploited. Free agency and player unions helped athletes earn better compensation.
Andrew feels rewarded by the possibility of helping hard-working athletes change the socioeconomic dynamic of their families and future families. Many of his clients are coming to the NFL with little money to begin with.
"I have some friends who are super successful in commercial real estate or corporate finance, and that really is working with, okay, how can we grow this company from being worth 800 million to 2 billion," Andrew said.
"That's a different thing than, hey, this is someone who grew up very, very, very modestly, and the first thing they're doing when they're signing their first pro contract is they're paying off their parents' debt on their house or something, right? That's a different deal. My favorite part of my job is the players and the families that I get to work with and represent."
Andrew and Jeffrey help each other out with problems that arise in their respective careers. Sometimes Jeffrey needs help with the practicalities of contract negotiations for his NFLPA work, helping to make sure rules in the CBA are worth their salt. Andrew can take advantage of Jeffrey's legal network to help with a client who needs a criminal defense attorney or tax specialist.
The two aren't working on any pending cases together at the moment. But with the NFL season about to heat up, the docket could soon change, and the force of the Kessler family would be felt again.
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