Fat Joe is a multi-million dollar success story, but he once missed out on a seven-figure payday due to his “tough guy” image.

The Bronx rapper recently sat down with Forbes and told a story about the time the CFO (chief financial officer) of a marketing agency tried to approach him with an offer to promote a beer company.

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The executive had a $2 million check in his pocket with Fat Joe’s name on it, but unfortunately for the Terror Squad leader, his sizeable entourage prevented it from reaching him.

“I was a real tough guy, Joe the Don, and I got the Terror Squad,” he began. “And so this man, I met him many years later. He was CFO of a marketing company out of Chicago. He passed away.

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“But he saw me in Miami. My wife is with me, we’re having mojitos. He said, ‘Man, let me tell you a story. I had a $2 million check for you from a beer company who said, ‘Get Fat Joe.’ This was when ‘What’s Luv?’ was number one.

“He said, ‘I came to the Bronx, I came to a club where you was at. You had about 40 guys around you and I saw you with my own eyes. I had a $2 million check in my pocket.’ He said he walked past the first 10, then grabbed him. ‘The Don don’t wanna speak to nobody.'”

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Joe continued: “This is a guy in a suit looking like you. He walked around another five. ‘The Don ain’t speaking.’

“He looked at me and said, ‘Wow, I have a $2 million check and I can’t even get to this kid. I can’t put this check in his pocket. As much as the company is telling me, ‘You better close that deal.” So that’s the stuff that you block — your blessings.”

Watch the conversation at the 19:13 mark below.

HHDX YouTube Video Player - Play ButtonYoutube Video - Fat Joe Recalls Missing Out On $2M Check Due To 'Tough Guy' Persona

This wasn’t the only time that Fat Joe missed out on a large sum of money at the height of his rap career. In his 2022 memoir The Book of Jose, he explained how his beef with 50 Cent cost him a $20 million deal with Air Jordan.

Joe blamed the collapse of the deal on the events that occurred at the 2005 MTV Video Music Awards, where he and 50 exchanged shots on stage. The two rappers and their respective crews also got into an altercation inside the venue before police intervened.

Fat Joe Recalls Being Robbed Of Millions By His Best Friend: 'He Feared For His Safety'
Fat Joe Recalls Being Robbed Of Millions By His Best Friend: 'He Feared For His Safety'

“I was supposed to be the first artist ever to collaborate with Jordan Brand,” he wrote. “I’ve always rocked the most Jordans, always had the 172 flyest, most exclusive Jordans out of any celeb. No one can compete with my sneaker collection.

“Me and Michael Jordan are actual friends. I met with him six times going over designs for the Fat Joe Jordan. Some of those meetings were literally just me and him, brainstorming, bouncing ideas off each other. But after the VMAs, Mike deaded the deal.”

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He continued: “‘You know I love you, Big Joe, but you’re too hot right now,’ he told me on a phone call. ‘I wanted to do it, but I’m not into all that rap beef. With all this controversy, we can’t do the sneaker anymore.’

“That was it. I lost about $20 million by not getting that deal. I lost out on other endorsements too. Promoters definitely didn’t book me and 50 Cent on the same shows. Everybody had to keep us separated. But as fate would have it, after the VMAs, we didn’t see each other again in person for almost a decade.”