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Sports Grid – Fresh out of BYU, Young bypassed the NFL to sign with the new United States Football League, which you most likely know. The deal? About $40 million over five years from the Los Angeles Express: the largest sports contract in history to that point. According to this, it would be equal to $90 million today, with inflation. Why that much with a fledgling football league? Because LA Express owner J. William Oldenburg was nuts. He wanted Young in the worst way, thinking that his all-out, rambling style of play would help establish his team, and the league, and position it to take on the NFL. But not only that: Oldenburg also had an arch-rival. Donald Trump was owner of the New Jersey Generals, and had splurged on NFL-quality talent such as quarterback Brian Sipe, defensive back Gary Barbaro and linebacker Jim LeClair. He even tried to lure Don Shula from the Dolphins to coach the team, but the story goes that Shula wanted a condo at Trump Tower as part of the deal, and The Donald declined. Oldenburg, desperate to prevent Trump from upstaging him, would get Young at any cost. The Cincinnati Bengals, who held the No. 1 pick in the NFL Draft, could have offered Young only the NFL rookie maximum of $500,000 per year over four seasons, not guaranteed, with a $1 million signing bonus. So it was kind of a foregone conclusion where Young would end up.

But it would be the weirdest contract in sports history. From CelebrityNetworth:

In order to make this contract work with the fledgling team, Steve agreed to a rather unorthodox deal. After his bonus, Steve would earn just $200,000 in year one, $280,000 in year two, $330,000 in year four and $400,000 in year five. The remaining $30 million would be deferred over 37 years starting when Steve turned 28 and ending when he was 65 in the year 2027. The contract was backloaded, which meant that the payments would escalate to $1 million per year in 2014, then $2.4 million and eventually topping out at $3.173 million in the contract’s final years. Furthermore, Steve signed a $100,000 a year endorsement deal with a Utah-based bank called State Savings Loan Association, which also happened to be owned by J. William Oldenburg.

Just to be safe, Steve’s agent [Leigh Steinberg] insisted that the contract be insured just like any other annuity that you would purchase from a bank. That meant Steve’s deferred $30 million was covered “in case the team or the league folds”. This final deal point would prove very wise.

Yep. Oldenburg went bankrupt in ’84, and the Express was shut down following the 1985 season. Just prior to that, Young bought out of his league obligation (although the annuity stayed intact), and went on to the NFL with the Buccaneers, and then the Niners. The USFL itself quit operations in 1987. The last USFL champion? The Baltimore Stars. Forever may they reign. The insurance company stuck with the bill, according to Sports Illustrated, is San Francisco-based Investment Mortgage International (IMI).

Move over Bobby Bo! You’ve got company. Fascinating story thats right up there with the John Spano buying the Islanders with absolutely no money. How does someone who’s broke in a fledgling league offer that kind of contract? More importantly, how the fuck does it get insured??? Thats gotta be the worst insurance agency on the planet. I don’t know much about he LA Express or the USFL but I’m pretty sure it had to be blatantly obvious the league was gonna fold in like 15 minutes. Certainly not stable enough to be out there guaranteeing 37 year annuities over 25 years later. But fuck em! Good for you Steve Young. Gonna collect anywhere between 1 and 3 million bucks a year from now until 2067. Perhaps the savviest financial decision in the history of sports.

Make sure you take The Donald out to dinner sometime in the next 37 years, Steve