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While free agency and trades have changed the landscape of professional sports, some athletes manage to spend their entire careers with the same franchise. One of those players was John Elway; the quarterback was drafted by the Baltimore Colts, but only suited up for the Denver Broncos. Today, he still works for the team as the general manager and president of football operations.

Elway’s attachment to the Denver Broncos, however, could have been even greater. He once missed out on an opportunity to buy a stake in the team and make himself $500 million richer in the process.

John Elway’s playing career with the Denver Broncos

In 1983, the Baltimore Colts selected John Elway with the first overall pick of the NFL draft. The quarterback had no intention of heading east, however, setting the stage for a trade with the Denver Broncos. That move would change the course of NFL history.

Although Elway had some growing pains in Denver, he eventually blossomed into a star under center. Within the first seven years of his career, the quarterback had already appeared in three Super Bowls; while the Broncos dropped all of those games, with Elway playing especially poorly against the San Franciso 49ers, he wouldn’t quit.

It took some time, but Elway eventually made it to the top of the mountain. The Broncos won Super Bowl XXXII at the conclusion of the 1997 season; the next year, they would repeat the feat. On the back of those wins, Elway rode off into the sunset. During his 16 seasons in the Mile High City, he went 148-82-1 while throwing for 51475 yards and 300 touchdowns.

Missing out on a $500 million chance to buy the Denver Broncos

During his playing career, John Elway earned over $45 million. He once passed up on a deal, however, that could have made him more than $400 million richer.

In September 1998, Broncos owner Pat Bowlen approached the quarterback with a proposition. According to Darren Rovell, Elway could “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 quarterback passed on the deal, later saying that he “did not see a place for himself as an executive of the team.” While he did go on to lead the Broncos to a Super Bowl that season, cashing out could have made him incredibly wealthy.

According to Forbes’ 2019 franchise valuations, the Broncos are worth $2.65 billion. If Elway had acquired 20 percent of the club, that stake would shake out to $530 million; even if he hadn’t accepted the second part of the offer and only purchased 10 percent, his $15 million investment would have turned into $265 million.

Things still worked out OK for John Elway, though

While missing out on a chance to buy a stake in the Denver Broncos turned out to be a pretty big blunder, things still worked out for John Elway. Despite some poor investments, he’s still in strong financial shape.

During his playing career, the quarterback started buying car dealerships; he eventually sold them to Autonation for $82.5 million in cash and stock but has since gotten back into the auto business. On the sporting front, Elway co-owned an arena football team before rejoining the Broncos. These days, he’s the team’s general manager and president of football operations.

The former quarterback reportedly makes $3 million per season and has a net worth of $145 million. Things could have been much different, however, if he took that one deal in 1998.