John Elway's lived a pretty charmed life. Star athlete at Stanford became one of the greatest NFL quarterbacks of all time who won back-to-back championships, rode off into the sunset, and eventually became the architect of the Broncos that has appeared in two of the last three Super Bowls. And throughout his 16-year career, Elway made some pretty decent money and tried to smartly invest it in various businesses, with varying degrees of success. 

But Elway's got to still be kicking himself for not saying yes to a sweetheart deal Broncos owner Pat Bowlen offered him in 1999 that would have made him worth nearly as much as Jay Z

ESPN's Darren Rovell has a fascinating examination of the deal Elway improbably said no to that would have in today's dollars made him worth at least $388 million.

The deal: Denver Broncos owner Pat Bowlen would give Elway the right to buy 10 percent of the Broncos for $15 million. Bowlen would also give him the option to buy another 10 percent of the franchise by forgoing the deferred salary Bowlen owed him on the condition Elway would become a special assistant to Bowlen, which would eventually lead to a COO job. That total deferred salary? About $21 million.

The deal was even sweeter than that. It had provisions that allowed Elway to sell his shares of the team if he wasn't satisfied after a few years for at least $5 million more than the original purchase price and he would have "right of first refusal to buy any other stake in the team if the Bowlen family sold to an outsider. NFL teams don't come up for sale often."

Sixteen and a half years later, as the Broncos are back in the Super Bowl, Elway is a paid employee of the team with no stake in the franchise. The 20 percent stake he passed on, based on a Forbes 2015 valuation of the team at $1.94 billion, is now worth $388 million, which would have been a 646 percent return on the 1998 investment, adjusted for inflation, had he made it.

According to Rovell, Elway's business acumen doesn't quite compare with his legendary quarterbacking skills. While there are examples of Elway hitting it big in business, like how he sold his car dealership for $82.5 million in 1997, Rovell outlined multiple times Elway lost big bucks. 

Elway squandered other money in more bad investments. Instances include:

  • In January 1998, Elway, with his coach Mike Shanahan, invested in a laundromat franchise called Laundromax. The company said it hoped to do for laundry centers what Blockbuster did for video rentals. Like Blockbuster, it failed to live up to the future.

  • In 1998, Elway invested in a Hispanic media company called Quepasa. He bought 133,333 shares for $500,000. By June 2000, after the stock had fallen from $27 to $1, he sold 33,000 shares at a $62,000 loss, according to SEC filings.

  • In August 1999, Elway invested a "seven-figure amount" in, an online sports e-commerce site, and became its co-chairman. A little more than a year later, it went bust.

The only appropriate reaction: ¯​\_(ツ)_/¯

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