SI Vault
Big Deals
Tom Verducci
June 14, 1993
For agents Scott Boras and Dennis Gilbert, baseball is a bonanza
Decrease font Decrease font
Enlarge font Enlarge font
June 14, 1993

Big Deals

For agents Scott Boras and Dennis Gilbert, baseball is a bonanza

View CoverRead All Articles View This Issue

Diamond Gems

Three times within a 30-month period Dennis Gilbert (above) negotiated the richest contract in baseball, as calculated on an average annual value basis. The $29 million deal with the Mets that he put together for Bobby Bonilla (inset) galvanized Gilbert's reputation as a smooth negotiator. Here is a recent chronology of baseball's highest-paid players.





June 27, 1990




Feb. 8, 1991




Dec. 2, 1991




March 2, 1992




Dec. 8, 1992




It is three weeks before the Amateur baseball draft, and the two preeminent player agents in the game can be found on the road, taking their typically divergent avenues to success. Scott Boras prefers the back roads. He is tracking a hot prospect in Baton Rouge, or maybe Sarasota, Fla., or Starkville, Miss., or some other college town or high school hamlet. All the while he is adding to the 900,000 miles in his frequent-flyer accounts and to the stable of gifted youth who entrust their careers to him.

Dennis Gilbert does not care about the draft. Gilbert's road is Hollywood Boulevard, and tonight the traffic is light. Behind the leathery wheel of his white Mercedes 500 SEL he has the look of a man who knows that the boulevard and the night and—oh, why not?—this whole town of make-believe belong to him. After all, hadn't Nicky and Charlie over at Nicky Blair's on Sunset welcomed him with hugs and offered him his usual table, the one near the painting by Tony Curtis?

Yes, it had been a good day, starting with the top page of his yellow legal pad on which he had written TO DO AND CALL in pencil above a long list of items. Barry Bonds had called earlier from a plane to request that a limo meet him at the airport. It was quickly arranged. Bobby Bonilla had called about a matter that needed checking, so one of Gilbert's associates at Beverly Hills Sports Council promised to get to it pronto and leave a message on Bobby Bo's 800 number. Tomorrow would bring a breakfast meeting with a high-ranking network TV executive.

But now the car phone and the car fax are silent, the Gucci watch on his wrist (pssst! it's a knockoff) says it is 11 p.m., and the marinara stain on his Canali suit does not appear to be setting (thanks to a dousing of mineral water). Gilbert is cruising the boulevard with no destination in mind. It is a rare moment of repose for a man known as Go Go, a man who has not taken a vacation in more than 10 years.

"I love this place," he says. Then he points toward a hillside where there is "a nice little restaurant" called Spago. Does he have a table there too? "No," he says, "but I have an understanding with them. I can get one when I need one."

If you're Dennis Gilbert, why bother with the amateur draft? He leaves that to others, people like the indefatigable Boras, who is the most despised agent of them all around baseball front offices. "When you find out that Boras is representing one of your players," says one National League executive, "it's, 'Oh, no!' " Such is Boras's notoriety that he sometimes resorts to scouting amateur players incognito or under an assumed name.

Says Gilbert, "Why should we compete in that arena when we're getting people and doing very well just by testimonials, people saying, 'These guys really take care of me.' We get 100 percent of our clients from referrals. I know the rap on us: 'Too big. Too Hollywood.' We have the best players in the game. We're not right for everyone, and we know that."

Boras and Gilbert are the agents of change in a financial marketplace they continually help redefine. Boras is a former medical litigation attorney who is loathed for his combative style. He represents many of the best young players in the game, including Jim Abbott, Steve Avery, Carlos Baerga, Kevin Brown, Greg Maddux and some of the top minor league talent. Gilbert made his mark by selling insurance to Hollywood stars, but his expanded services now attract the marquee names in baseball too. Bonds, Bonilla, Jose Canseco, George Brett, Bret Saberhagen and Danny Tartabull are among his 60 or so clients. Gilbert is the kind of guy people describe as "well connected."

"One guy's a salesman, and the other's a warrior," says Chicago White Sox owner Jerry Reinsdorf. "Dennis is smooth. While he's taking your money, he makes you very happy. Boras presents problems because of his approach. One of the biggest differences between the two is that Boras wants to get the last bottom dollar out of you. Gilbert wants that last dollar too, but not at the expense of hurting a relationship between the player and club. I believe Boras doesn't care about relationships. Boras has done more than anyone to raise the price of amateur talent, and Gilbert has a knack of attracting the important stars. So they're both very important players on the baseball scene."

Gilbert, 45, was a minor league outfielder in the Boston Red Sox, New York Met and Kansas City Royal systems between 1968 and '71. At age 23, realizing he ought to seek another career, he started selling life insurance in Los Angeles, much of it door to door. Seven years later he established his own agency, and by the time he was 35 he was driving a Rolls-Royce with GO GO 19 plates (19 was his number in the minors) and making a name as "the insurance salesman to the stars," with Michael Landon, Rod Stewart and Sally Field among his clients. On his way to meetings with Lorne Greene, he would hum the Bonanza theme song.

Continue Story
1 2 3 4