11 Pro Athletes Who Pivoted To An Unexpected Career After Retiring

Some professional athletes make enough money during their career to never have to work a day for the rest of their lives after calling it quits, and many others keep busy by getting a job in the media, as a coach, or in a front office. However, there are plenty of others who’ve turned their attention to a wildly different pastime.

It’s easy to say you’d opt to rest on your laurels if you were a pro athlete who made the kind of money that ensures you’ll never have to worry about your finances again, but there aren’t many people who find satisfaction in an aimless existence where you simply float through life for decades on end.

There are a ton of former athletes who probably didn’t need to get another job after they left their sport behind only to decide to pursue another career, and more than a few of them opted to embark down a path most people probably wouldn’t have seen coming.

Here are some of the most interesting examples.

Jake Plummer: Mushroom Farmer

Career Earnings: ~$59 million

Jake Plummer was about as close to the definition of average that you can get during a 10-year NFL career where the quarterback spent six seasons with the Cardinals and another four with the Broncos (he posted a 69-67 record as a starter).

Plummer became a vocal advocate for medical marijuana after he retired in 2007, and he’s gone all-in when it comes to throwing his support behind natural therapies since then.

The QB who was nicknamed “The Snake” eventually co-founded Umbo, a company that makes mushroom-based supplements, alongside former UFC fighter Rashad Evans.

That venture inspired him to gain a deeper understanding of the fungi, and he’s expanded his knowledge with the help of the mushroom farm he owns in Colorado.

Drew Bledsoe: Winemaker

Career Earnings: $80 million

Drew Bledsoe may be best remembered as the guy who got replaced by Tom Brady right before the Patriots entered Dynasty Mode, but that’s a bit of a disservice to a man who had enough talent to spend 14 seasons in the NFL as a quarterback.

The Washington native used some of his earnings to buy property in Walla Walla before opening the Bledsoe Family Winery that produces vino under two different labels: Doubleback and Bledsoe-McDaniels.

Bryant Reeves: Cattle Farmer

Career Earnings: $55 million

Bryant Reeves was an Absolute Unit, as the seven-footer who weighed upwards of 300 pounds played basketball at Oklahoma State before spending six seasons as a member of the Grizzlies.

The Oklahoma native lived up to his “Big Country” nickname in more ways than one—including his decision to buy a 300-acre ranch where he built his dream home near the banks of the Arkansas River.

Reeves turned the property into a cattle ranch where he resides with his family while taking care of the animals that serve as their primary source of income now that he’d put basketball behind him.

Jared Allen: Curler

Career Earnings: $98 million

Jared Allen spent 12 years in the NFL as a defensive end for the Chiefs, Vikings, Bears, and Panthers and was a sack machine who left football behind in 2016.

However, it didn’t take him very long to find a new passion in the form of…curling, the sport that’s really only thrust into the spotlight every four years at the Winter Olympics.

Allen initially teamed up with a few other guys who played in the NFL in the hopes of qualifying for a spot in the Olympics. He hasn’t checked that box, but in 2024, he partnered with a couple of Canadian curlers to purchase the rights to the Grand Slam of Curling.

Mookie Wilson: Truck Driver

Career Earnings: N/A

Mookie Wilson played in the MLB for 12 seasons and is probably best remembered as the guy who hit the ball that skipped through Bill Buckner’s legs during the 1986 World Series.

He stayed involved with baseball by working as a coach after he retired, but in 1999, he started to pursue a new gig in the offseason with the help of a tractor-trailer truck he bought to start making deliveries around the United States.

Wilson didn’t need the extra cash but decided to start hauling stuff because he enjoyed the journeys the job took him on, saying the money was really just a bonus.

Randy Johnson: Photographer

Career Earnings: $175 million

Randy Johnson was a force to be reckoned with on the mound during a Hall of Fame career where the 6’10” man who was deservedly known as “The Big Unit” racked up over 300 wins and 4,875 strikeouts (putting him behind only Nolan Ryan for the most of all time) during his 22 MLB seasons.

Johnson was no stranger to having cameras pointed on him when he was pitching, and he got to get a taste of what it’s like to the be the person on the other side of the lens when he started his own photography company—one with a logo that features a dead bird as a nod to the most infamous moment of his career.

Ken Griffey Jr.: Also A Photographer

Career Earnings: $172 million

Randy Johnson emerged as one of the best pitchers in the MLB around the same time Ken Griffey Jr. cemented himself as one of its most electric sluggers, and the latter also spent a grand total of 22 seasons in the league en route to being inducted into the Hall of Fame.

That’s not the only thing they have in common, as “The Kid” also took up photography in retirement—a development that first came to the attention of many people in 2025 when he gained the credential required to be one of the few people who are permitted to snap pictures at The Masters.

 

Mark Hamilton: Doctor

Career earnings: $3 million

Mark Hamilton never came close to becoming a household name during his brief time in the MLB, as he only appeared in 47 games during the two seasons when he was a member of the Cardinals at the start of the 2010s (he did get a World Series ring for his contributions in 2011).

Hamilton called it quits after being cut by the Triple-A affiliate for the Braves in 2014, but he already had a backup plan in mind: medical school.

The infielder managed to get his degree at Hofstra’s Zucker School of Medicine. He initially planned to be an orthopedic surgeon but decided to switch to interventional radiology and currently practices on Long Island.

Junior Bridgeman: Restaurant And Soda Mogul

Career Earnings: $3 million

Junior Bridgeman spent 12 seasons in the NBA (10 with the Bucks and two more with the Clippers) and had a solid career despite coming off the bench for the bulk of it.

He was still playing when he got the chance to invest in a Wendy’s franchise in Chicago in 1984, and when he retired three years later, he opened one of his own in Brooklyn.

That marked the start of an empire where Bridgeman would come to operate more than 160 Wendy’s locations and close to 120 Chili’s outposts that he eventually leveraged to buy a bottling plant that distributed Coca-Cola.

It was widely believed he was worth well over $1 billion before he passed away in 2025.

Roger Staubach: Real Estate Mogul

Career Earnings: $500,000

Roger Staubach spent 11 seasons playing quarterback for the Cowboys and led the team to two Super Bowl victories during a tenure where they played in The Big Game on five occasions (he was also named the MVP of Super Bowl VI).

The QB started planning for life after football while he was still playing in the NFL, as he knew he’d have to find another job to support himself and his family once he hung up his cleats due to the underwhelming nature of the salaries that were handed out during the era he played.

Staubach started studying real estate management in the offseason before retiring and ended up doing very well for himself while running The Staubach Company, which sold for over $600 million in 2008.

Byron White: Supreme Court Justice

Career Earnings: ~$50,000

This one is a bit of a throwback, and “unexpected” probably isn’t the right word to use here based on his background.

With that said, I’m not sure how I can’t include a man who initially made a name for himself as a football player before ending up behind the bench in the Supreme Court.

White excelled at football and academics at the University of Colorado, as he was an All-American halfback and Rhodes scholar who postponed his term at Oxford so he could play in the NFL.

The man who was dubbed “Whizzer” led the league in rushing during his rookie season with the team that would eventually become the Steelers in 1938, but he stepped away from football the following year so he could pursue a law degree at Yale.

He ended up playing for the Lions for two more seasons before joining the Navy in WWII. He never returned to football, but he did embark on a law career that peaked when John F. Kennedy appointed him to the Supreme Court in 1962—a post he held for over 30 years before retiring in 1993.