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Bobby Bonilla Day: The story behind the best baseball contract ever

The most interesting holiday of America’s favorite pastime comes just three days before the country celebrates its independence.

On July 1 of every year from 2011 to 2035, the New York Mets have and will write a $1.19 million check to former player Bobby Bonilla — even though he hasn’t suited up for the team in the 21st century.

“We got a guaranteed 8% interest rate,” Dennis Gilbert, the sports agent who negotiated the contract for Bonilla, told Yahoo Finance (video above). “Made it work and gave him income all the way through age 65.”

Bobby Bonilla's contract with the Mets after the 1999 season created "Bobby Bonilla Day" (July 1). (Photo: Yahoo Finance)

The Bronx native will be paid in roughly $29.75 million over the course of the contract — and it all sprang from a $5.9 million salary owed to Bonilla for the 2000 season.

“No one really knew about it until it came news,” Bonilla told Yahoo Finance. “It was pretty funny that all of a sudden now it became this thing. Every time I look at Dennis, I say: ‘Thank you.’”

1999 was ‘probably the most difficult year’ for Bonilla

Roberto Martin Antonio Bonilla last stepped on the field wearing the Mets’ dark blue and orange colors in the last game of the 1999 regular season when he grounded out to Pittsburgh Pirates’ first baseman Kevin Young as a pinch hitter in the bottom of the ninth inning.

Following their expulsion from the postseason, the kings from Queens immediately went into restructuring the roster, starting with Bobby Bonilla. After all, in the 1999 season, the outfielder played 60 games and hit .160.

“Yeah, '99, which is probably the toughest year play. The one year I went back with the Mets, probably the most difficult year,” Bonilla said.

New York Mets right fielder Bobby Bonilla drops a fly ball for an error in the first inning against the Colorado Rockies in New York, April 8, 1993. Bonilla and the Mets recovered to win 6-1. (AP Photo/Ron Frehm)

In his 16 years in the league with eight teams, Bobby Bo collected three-time Silver Slugger awards, six MLB All-Star selections, and a World Series ring with the 1997 Florida Marlins.

The Mets traded for Bonilla before the 1999 season from the Los Angeles Dodgers for relief pitcher Mel Rojas. The trade meant taking on the final two years of a $23.3 million contract that would have the boys from Flushing paying $5.9 million a year.

New York Mets Bobby Bonilla hits a grand slam against the San Francisco Giants in the second inning, June 1, 1992 at New York's Shea Stadium. (AP Photo/Osamu Honda)

Bonilla made waves in 1999 — but mostly for his struggles on and off the field. He struggled to get on base and he fought with the press and Mets management, including namesake and manager at the time Bobby Valentine.

His most infamous moment during the season came in the sixth game of the NLCS match against the Braves when he was spotted playing cards in the clubhouse with future Hall of Famer and teammate Rickey Henderson.

New York Mets outfielders Bobby Bonilla, left, and Rickey Henderson joke around at spring training Tuesday, Feb. 23, 1999 in Port St. Lucie, Fla. Bonilla played in 1998 for the Florida Marlins and Los Angeles Dodgers. Henderson was with the Oakland A's. (AP Photo/Mark Lennihan)

How the famous contract came to be

The Mets had enough, and so they met up with Bonilla’s agent and agreed on a deal that would go down in the Hall of Fame of retirement plans.

“The general manager of the Mets needed to free up some money to sign some free agents or to sign a free agent. He needed to have the money now to pay the free agent,” said Gilbert, CEO of the Gilbert Group and a special assistant to the Chicago White Sox.

Gilbert, who played alongside Dock Ellis in high school and dreamed of becoming the owner of the Dodgers, was known around the baseball world as someone who would give both sides of the aisle a fair deal. And the deal became to defer the $5.9 million the Mets owed Bonilla in 2000 in lieu of paying Bonilla in installments from 2011 to 2035.

Dennis Gilbert sitting in his The Gilbert Group insurance office in Beverly Hills, California. (Photo: Yahoo Finance)

And by releasing Bobby Bo and signing the deal, the Mets freed up $6 million to sign free agent Mike Hampton, who went on to become the 2000 NLCS MVP. And when Hampton left after the Metropolitans lost to the New York Yankees in the World Series, the team was awarded the draft pick that would become team legend and former captain David Wright.

The Bernie Madoff connection to Bobby Bonilla’s contract

This sort of deal occasionally occurs in professional baseball.

“Remember, it's not what you make or what you have. It's what you keep,” said Gilbert. “Deferred compensation helps you keep your money.”

The Atlanta Braves paid Bruce Sutter’s $45 million over 30 years, and the Boston Red Sox are paying Manny Ramirez — who last played for the team in 2008 – about $30 million total from 2011 to 2026. Gilbert — who has represented players such as Barry Bonds, Jose Canseco, Mike Piazza, and Henderson — worked out deferment deals for other players such as Bonilla’s former teammate Bret Saberhagen.

That said, Bonilla’s circumstances are special enough that journalists began referring to July 1 as “Bobby Bonilla Day.”

Part of what made Bonilla’s situation unique was that Mets owner Fred Wilpon was heavily invested in the massive Ponzi scheme run by his pal Bernie Madoff that promised a guaranteed 10-15% return each year.

Bernard L. Madoff leaves US Federal Court after a hearing regarding his bail on January 14, 2009 in New York. (Photo: TIMOTHY A. CLARY/AFP/Getty Images)

Federal authorities arrested Madoff on December 11, 2008, and he was convicted of various kinds of fraud, money laundering, false statements, perjury, and more. Wilpon lost an estimated $700 million in the scam.

Another wrinkle is that the Mets are actually paying two separate deferment contracts to Bonilla. The New York native signed a five-year, $29 million contract — MLB history’s largest at the time — starting in 1992 before being traded to the Baltimore Orioles in 1995.

Gilbert claims that the contract would push the deferment payout to around $50 million, though the details of the deferment deals are not clear. In any case, not bad for a slugger who made career earnings of $46.45 million for his playing time.

“I will tell you,” Gilbert said as we spoke to Bonilla over the phone, “you’re the first person he’s talked to [about this] in a lot of years.”

Video and reportage by Yahoo Finance Producer Ignazio Monda.

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