For most NFL players, payday is the best part of the week. They even begin spending right away. But for former San Francisco 49ers quarterback Steve Young, it was a different story. Getting a paycheck while being on the sideline felt like an insult to his pride. To make things even, he decided not to use the paychecks he got while sitting on the sidelines. But little did he know that he’d have to give the checks away. 

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“When I wasn’t playing, the one thing I didn’t want to do was sit around,” Young recalled during his appearance on In Depth with Graham Bensinger. “I’d rather go to law school and sit and watch. This is the immaturity and stupidity of me. I was like, ‘I’m not gonna cash my check. I’m just going to let it sit in the drawer, because I’m not playing. So, it doesn’t matter.

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“I was renting a little room from Harris Barton, my teammate, and I went back to law school when the offseason and Carmen policy called me and general manager of the team, and said, ‘Hey look, you’re screwing up the taxes. Where’s the checks, man? It’s April. We gotta file.’ I forgot I left them in the drawer in Harris’ house.”

Young dialed up Barton’s number and asked him to go to his room and check his drawer for the checks. Needless to say, finding 16 massive checks surprised Barton. Bensinger even pointed out that those checks must amount to somewhere around $4 million. 

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“I said, ‘Do me a favor, man. Would you gather them and send them to me?’” Young recalled. “Back then, couldn’t take a picture of it or anything. So, he sent them to me. I finally gave in because of the audit for the 49ers. Reluctantly gave in.”

Before he ever took over the reins in the Bay Area to win two league MVPs and Super Bowl XXIX, Young spent four frustrating seasons (1987–1990) stuck in the shadow of another 49ers legend, Joe Montana. But instead of sulking, he went on to earn a law degree from Brigham Young University’s J. Reuben Clark Law School in Provo, Utah. 

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Looking back, the fact that Young nearly triggered an IRS headache for Carmen Policy and the 49ers is even more ironic given his post-football career. After hanging up his cleats in 1999, Young co-founded HGGC. It’s a Palo Alto private equity firm that manages billions of dollars in capital commitments. 

Nevertheless, his relentless work ethic paid off in 1994. Young earned his Juris Doctor degree from BYU and led the Niners to a Super Bowl win. He spent 15 years in the league and threw 2,667 completions for 33,124 yards and scored 232 passing touchdowns. He also won two league MVP awards and three Super Bowls, including one as the starting quarterback in Super Bowl XXIX. The former quarterback definitely found a way to bounce back. 

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