Berry is a Co-Head of CAA Sports' Baseball division. Forbes ranked Berry as one of the world's most powerful sports agents and said of CAA, "For every tiny step the competition takes, CAA seems to make a giant leap." In his two decades as an agent Berry has negotiated a number of landmark contracts, including record-setting deals for Jacob deGrom ; Buster Posey ; Wil Myers, ; Ian Desmond and Matt Cain. Berry also has a record as a fierce advocate for players, writing a memo in 2018 that outlined strategies for players to empower themselves in the labor battle. Berry told ESPN.com, "As advocates, our job is to fight for and protect player rights, and when necessary, try and help create solutions -- not pointing fingers of blame and hoping things get better. And I wholeheartedly believe there are viable solutions to the core labor issues facing the game that can be remedied to the benefit of players, clubs and fans." CAA advised four of the top 20 picks in the 2019 draft and two of the top five picks in the 2017 draft. In 2017, Berry advised Vanderbilt pitcher Kyle Wright, who received a $7 million signing bonus from the Atlanta Braves — $1,292,700 above the slot value, a first-round record in the current draft system. CAA also advised Hunter Greene, who signed with the Cincinnati Reds for $7,230,000, setting a record in the current system. In the 2018 draft, Berry advisee Jordyn Adams, who had a football scholarship to North Carolina, went 17th overall to the Los Angeles Angels. That was $627,100 above slot, most of any high school first-rounder in that draft. Former major-league General Manager Jim Bowden, writing for ESPN.com, described Berry as "an attorney who has a direct and no-nonsense negotiating style and vehemently fights for his clients. He is hard-nosed, at times stubborn and prefers to stay in the box in terms of negotiations." In 2008, Berry negotiated the largest signing bonus in baseball draft history, Posey's $6.2 million deal with San Francisco. Berry has negotiated other precedent-setting draft deals: for Myers with the Kansas City Royals, A.J. Cole with the Washington Nationals and Dillon Maples of the Chicago Cubs. Berry has been involved with multiple rule changes in baseball. Following Posey's season-ending injury in May 2011, Berry lobbied Major League Baseball and the players' union to limit home-plate collisions, telling ESPN.com, "You leave players way too vulnerable.... I don't know if this ends up leading to a rule change, but it should. The guy is too exposed.... I'm going to call Major League Baseball and put this on the radar. Because it's just wrong." Eventually MLB added Rule 7.13 to protect catchers. In 2014, word leaked that shortstop prospect Trea Turner was the player to be named in a trade between the San Diego Padres and Nationals but could not actually be traded, by rule, for six more months. Berry told foxsports.com, "Given the circumstances and the undoubtedly negative impact on Trea Turner, for the teams involved and Major League Baseball to endorse and approve this trade is not only unethical, but also goes against the very spirit of the Minor League Uniform Player Contract that players sign when they first enter professional baseball." In May 2015, MLB revised its rules and allowed players to be traded in the fall after they were drafted. In June 2015, Berry successfully appealed an eight-game suspension of client Will Smith of the Milwaukee Brewers for having a foreign substance on his arm, getting the suspension reduced. Smith credited Berry for the victory, saying, "My agent did his homework and cracked down on it. I felt comfortable leaving the meeting very well-represented." Berry has also helped enable trades for his clients to preferred destinations. Shortly after he told ESPN.com in December 2009 that Roy Halladay would not approve any trade after he reported to spring training, the Toronto Blue Jays dealt Halladay to the Philadelphia Phillies, who signed Halladay to a $60 million extension. In 2019, Berry said client J.T. Realmuto would not sign a long-term deal with the Miami Marlins, and by February, the Marlins traded Realmuto to the Phillies.
Personal
Berry and his wife Sarah have three children, two sons and a daughter. Berry is a frequent speaker at colleges, law schools and other events. In 2016, Berry appeared on the Dick Vitale Telethon to benefit pediatric cancer research for the V Foundation.
