Life after baseball isn’t always sunshine, golf courses, and honorary first pitches. For some of the game’s biggest names, the transition out of the spotlight was rockier than a 40-foot curveball in Colorado.
Whether it was failed business ventures, personal setbacks, or bad luck, these former MLB stars discovered that the real world doesn’t care much about your career batting average. Here are legends whose post-retirement lives came with a big ol’ slice of humble pie.
14. Jose Canseco
He went from MVP to reality show punchline faster than one of his home runs left the yard. After baseball, Canseco dabbled in everything from boxing to writing tell-alls, with more Ls than Ws.
13. Dwight Gooden
Gooden’s post-career life has been filled with personal battles, legal run-ins, and rehab stints. Despite a legendary start to his career, retirement has been anything but smooth.
12. Pete Rose
Baseball’s all-time hits leader is still banned from the game and spends his time doing autograph signings in Vegas. It’s not quite Cooperstown, but at least the casinos have air conditioning.
11. Denny McLain
The last pitcher to win 30 games in a season ended up serving time in prison after his playing days. Not exactly the kind of “second act” they write movies about.
10. Curt Schilling
Schilling went from postseason hero to political firestarter and business bust. His video game company’s collapse and social media controversies made headlines for all the wrong reasons.
9. Darryl Strawberry
Strawberry’s story has been a roller coaster of redemption and relapse. He’s now found purpose in ministry, but the road there was paved with some serious off-field struggles.
8. Roger Clemens
The Rocket’s retirement has been defined more by courtrooms than clubhouse nostalgia. His repeated battles over PED allegations left his legacy more complicated than celebrated.
7. Lenny Dykstra
Dykstra’s post-baseball life included bankruptcy, jail time, and wild headlines that sounded more like tabloid fiction. His playing career might’ve been gritty, but his retirement has been grimy.
6. Sammy Sosa
Sosa’s transformation post-retirement has been more baffling than endearing. From changing his appearance to a bizarre exile from Cubs history, it’s been a confusing chapter for the former slugger.
5. Barry Bonds
Despite being among the most dominant hitters, Bonds has struggled to find a meaningful role in the game post-retirement. The Hall of Fame door remains shut, and public sentiment hasn’t softened.
4. Mark McGwire
McGwire eventually returned to baseball as a coach, but the steroid era still casts a long shadow. His once-heroic image has taken more hits than a batting practice screen.
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3. Manny Ramirez
Manny, being Manny, has now become Manny bouncing around the world in search of one more paycheck. Retirement didn’t slow him down—it just made things much worse.
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2. Alex Rodriguez
He’s reinvented himself as a media mogul, but let’s not forget the PED scandal, the suspension, and a public image overhaul that took a whole marketing team to fix. A-Rod may be rich, but it was a bumpy road getting there.
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1. Rick Ankiel
Ankiel’s story is both humbling and inspiring. He went from phenom pitcher to completely unraveling on the mound, only to reinvent himself as an outfielder—proof that life after a fall can still have a second chapter, even if it’s not the one you planned.
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