Who was Bobby Bonilla’s agent Dennis Gilbert? All about the mastermind behind Bobby Bonilla Day

Every July 1, baseball fans take joy in Bobby Bonilla Day, a holiday spawned from one of the oddest contracts in sports history.

Former MLB player Bobby Bonilla may not have played a professional game since 2001, but he’s still making $1.19 million per year from the New York Mets until 2035. Central to this now iconic deal is his agent, Dennis Gilbert, the genius behind the framework that allowed it to happen.

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According to Fox News, a former minor league baseball player, Gilbert moved into the insurance industry before becoming a co-founder of the Beverly Hills Sports Council, a major agency that represented a lengthy roster of prominent baseball stars, such as Barry Bonds, George Brett, Jose Canseco, and Bonilla.

Gilbert entered the sports agency business after assisting his best friend, George Brett, with a contract negotiation with the Kansas City Royals.

The Bonilla deal of 2000 occurred when the New York Mets sought to receive $5.9 million in buyout money from Bobby Bonilla. Instead of taking the money up front, Gilbert worked out a deferred payment scheme in which Bobby Bonilla got annual payments of almost $1.2 million, with 8% interest, over 25 years starting from 2011 (CNN News).

The Mets during that time believed that they would reap far more in investment returns and therefore agreed to Gilbert’s proposal.

A look into Dennis Gilbert's other clients and legacy amidst Bobby Bonilla's increased payout

Thanks to the pay structure of rookie contracts in Major League Baseball, many of the league’s best young players start their careers much lower on the pay scale than Bonilla’s $1.19 million.

According to a report provided by LWOSports, Chicago Cubs outfielder Pete Crow-Armstrong will supposedly make $771,000 this year. The Washington Nationals' James Wood will receive around $764,600, and Riley Greene is also said to be making $812,400. By the end of the contract in 2035, Bonilla will have made almost $30 million when compared to the $5.9 million buyout.

In a 2021 interview on the Flippin' Bats Podcast, Gilbert stated that his inspiration to make these types of deals came from former players in retirement who were financially struggling. He hoped to provide financial stability over the long term for his clients, something that traditional contracts did not always guarantee.

"You know, I had a lot of friends that were coming out of the game of baseball, and they were running out of money. I was trying to think of what I could do and was thinking of some ideas of how to go about it, and this is what I came up with. This isn’t the only deal I did like this." Gilbert said during the podcast.

Bobby Bonilla was not Gilbert’s only client with a payment deferral agreement. Pitcher Bret Saberhagen also signed a comparable, although less lucrative, deal with the Mets.

In addition to being a sports agent, Gilbert has continued to be in touch with the baseball world. He is now a special assistant to the owner of the Chicago White Sox, Jerry Reinsdorf, still providing guidance on player contracts and team matters.

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