John Elway is a successful man. On the field, he’s earned two Super Bowl rings and a golden jacket. Up in the box, he’s constructed a champion and perennial winner. Outside of football, he built one of the most successful car dealership chains in America.

When John Elway sees an opportunity to succeed, he doesn’t often miss.

Except that one time …

Had Elway acquired 20 percent of the Denver Broncos back in 1999, not only would he have earned nearly $450 million in the span of 18 years, but he’d likely have a real chance at becoming the Broncos’ next majority owner.

Of course, the Broncos are expected to remain within the Bowlen family for the foreseeable future, but had Elway been a part-owner for the last decade and a half, who knows how things may have changed.

Luckily, he still has a pretty good gig going for him.