Scott Boras may have the most impressive client list of any agent in baseball today, but it wasn’t long ago that he shared that title with Dennis Gilbert. From the early 80s until his retirement in 1999, Gilbert was in charge of negotiations for some of the biggest names in the game, from George Brett to Jose Canseco to Barry Bonds. He built a reputation for getting top dollar for his players and churned out record-smashing deals for his top clients. Ultimately, however, Gilbert sold his powerful Beverly Hills Sports Council at a young age, then got back into the game a couple years later as a special assistant to White Sox chairman Jerry Reinsdorf.
Throughout his career, there’s been one constant for Gilbert: the life insurance business. When a friend of his who worked as a baseball agent passed away unexpectedly, Gilbert took over for some of his clients and quickly built his business from there. Still, he never left the insurance industry and juggled both by surrounding himself with the right people in both worlds. It was an impressive feat, given the amount of attention and hours that being a baseball agent requires.
In 1993, Tom Verducci of Sports Illustrated wrote a tremendous piece comparing Boras and Gilbert when they were both at the top of the business. The consensus from around the game was that the two men achieved their success quite differently. “One guy’s a salesman, and the other’s a warrior,” Reinsdorf told Verducci. “Dennis is smooth. While he’s taking your money, he makes you very happy.”
It may be a cliche, but Gilbert is one of a kind. He still greets people with warmth and a few card tricks, and he tends to make lasting impressions. There was no one in his field in the 1980s or ’90s who had a comparable demeanor, and there’s no one now either, nearly 15 years after he transitioned out of the business.
“I don’t have a ton of interaction with agents on a daily basis, but I don’t think any of them do. My approach was unique and I built some strong relationships during that time,” Gilbert tells MLBTR.
Gilbert had a strong rapport with executives around the league, but he had more than one client who rubbed folks the wrong way. Canseco was viewed as a brash and arrogant; Bonds’ rep was as a standoffish individual who didn’t care for the media. Of course, the stain of steroids didn’t help either player’s image. To hear Gilbert tell it, most people didn’t have a full idea of what either man was about and chose only to zero in on the more odious aspects of their personalities.
“The part of Jose that I know about was when he had money he gave his money to his father, mother, sister, brother and a lot of friends around him and he just took care of a lot of people. He had a very big heart and I think that’s a part that people never saw,” Gilbert says. “Barry did a lot of things under the radar also. Going to children’s hospitals, signing dozens of bats every year and handing them out and doing a lot of things that people weren’t cognizant of. They both had soft sides to them.”
Gilbert’s relationships with certain people in baseball continued even after he sold off the BHSC. He was Mike Piazza’s agent during much of his Dodgers prime, and even though Gilbert was no longer representing the catcher towards the end of his stay there, he was “in the room” around the time when Piazza was traded to the Marlins. Once again, in Gilbert’s mind, public perception didn’t quite match reality. As most Dodgers fans understand it, the new FOX ownership group was reluctant to pay the All-Star catcher fair market value on his next contract, necessitating the trade to Florida. On the contrary, Gilbert says that Rupert Murdoch’s baseball arm did everything it could to make things work.
Today, he’s on call for “anything that Jerry Reinsdorf needs” in his role with the White Sox and says that he’s optimistic that the club will have a quick turnaround after a down 2013. He’s considered team ownership, with exploratory talks to purchase the Rangers and, most recently, the Dodgers. One might think that he’s wistful for his days as one of the very top agents in the game, but that’s not exactly the case. Gilbert says that he enjoyed negotiating the contracts and “the baseball part” but isn’t wild about some of the outside stuff the job also calls for. His future could take him in a number of directions, but it’s safe to say that he won’t be sitting opposite of Reinsdorf at the negotiating table again.