Berry was born in Owensboro, Kentucky. He attended the University of North Carolina at Charlotte, where he was a catcher on the baseball team. After graduating with a Bachelor of Science in Business Administration, Berry signed with the Boston Red Sox, and spent one season as a catcher in their minor league system. Following his playing career, Berry was a Graduate Assistant Baseball Coach at Oklahoma City University, from 1995 to 1998. While at OCU, he earned his Juris Doctor from the University's School of Law, graduating cum laude in May 1998. Berry is a member of the Oklahoma Bar Association and a certified agent with the Major League Baseball Players Association.
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."
Since the end of the 2011 season, Berry has negotiated more than a half-billion dollars' worth of contracts, including record-setting deals for Buster Posey (nine years, $167 million with the San Francisco Giants, the longest contract ever for a catcher and richest ever for a player with fewer than four years' service time); Ian Desmond (the largest free-agent deal for a position player in Colorado Rockies history) and Matt Cain (six years, $127.5 million deal with the Giants, which set a record guarantee for a right-handed pitcher).
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 Wil Myers with the Kansas City Royals ($2 million, a third-round record), A.J. Cole with the Washington Nationals ($2 million, a fourth-round record) and Dillon Maples of the Chicago Cubs ($2.5 million, a record for anyone picked after the third round).
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 [at the plate] 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 (baseball) 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 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.