3) Bad NY Mets contract: Bobby Bonilla's deferments in his contract made the team a punchline
Bobby Bonilla returned to the Mets in 1999 for a secound stint in orange and blue as part of the Florida Marlins firesale following their 1997 World Series win. But he grossly underperformed that season and the Mets released him before the 2000 season, and the Mets didn't want to pay him. It didn't help that he was found playing cards with Rickey Henderson during Game 6 of the 1999 NLCS against the Braves when facing elimination after both were removed from the game.
So the Mets decided to defer the $5.9 million salary he was owed in 2000 into annual payments with an 8 percent interest such that he would be paid $1.19 million annually (or nearly $30 million overall) for 25 years. Because the Wilpons were banking on Bernie Madoff's firm to return large profits to their ownership, they decided to delay the start of those payments from 2000 to 2011.
However, In 2008, it was revealed that Madoff ran a Ponzi scheme and duped the Mets, setting off a firestorm in the organization and it crippled the Wilpons financially, and the Mets couldn't spend money on free agents the way they used to, forcing them into a rebuild and hiring Sandy Alderson to lead that rebuild.
The Mets will pay Bonilla annually on July 1 every year until 2035, and Mets fans will be subject to national media jokes on that day until then.