Wrestling fans are a cynical bunch. Honestly, we’ve seen it all. But there is still something about that neon-colored briefcase that makes a grown adult scream like a kid. It’s the "contract." The golden ticket. For over twenty years, the list of Money in the Bank winners has served as a crystal ball for who WWE thinks is actually going to be the next "guy" or "girl." Or, occasionally, it’s just a tool to ruin someone's night for the sake of a Twitter trend.
Look at the 2025 results. Seth Rollins. Again.
At Money in the Bank 2025, Rollins became only the second man in history to win the match twice, joining CM Punk in that very exclusive club. He beat out LA Knight, Penta, and Solo Sikoa in a match that literally featured a "Fireball Ladder." This wasn't just a win; it was a statement. But the history of this match is littered with people who grabbed the briefcase and then... basically vanished.
The Heist, The Heartbreak, and The Weird Ones
When we talk about Money in the Bank winners, everyone immediately jumps to Seth Rollins at WrestleMania 31. The "Heist of the Century." You remember it. The sun setting over Levi’s Stadium, Roman Reigns and Brock Lesnar beating the absolute hell out of each other, and then that music hits.
It changed everything.
Before that, the rules were simple: you wait until the champion is half-dead after a match, run down, and pin them. Rollins decided to turn a singles match into a Triple Threat while it was happening. It was genius. It was also a massive risk that the company took on a guy they weren't 100% sure about yet.
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Then you have the 2024 winners. Tiffany Stratton and Drew McIntyre. Tiffany is basically carrying that briefcase like a high-fashion accessory, and it works. It’s iconic. But Drew? His 2024 win was a tragedy. He cashed in the same night, got screwed by CM Punk (obviously), and lost. He became part of a smaller, much sadder list: the failed cash-ins.
Why Some Winners Fail (And Others Fly)
It’s not always about the talent. Sometimes, the writers just get bored.
- Baron Corbin (2017): He lost his cash-in because of a distraction from John Cena. Honestly, it felt like a punishment.
- Damien Sandow (2013): He cashed in on a one-armed John Cena and still lost. That’s a career-killer.
- Austin Theory (2022): This was the weirdest one. He cashed in for the United States Championship. Not a World Title. And he still lost. Sorta felt like they just wanted the briefcase off him.
Compare that to Edge. The original. The "Ultimate Opportunist." Back in 2006, nobody knew how this was supposed to work. Edge waited for John Cena to survive an Elimination Chamber match. Cena was a bloody mess. Edge walked in, two spears later, and the blueprint for the next two decades was born.
The Two-Time Club: Punk and Rollins
Winning once is luck. Winning twice is a legacy.
CM Punk did it back-to-back in 2008 and 2009. People forget how controversial that was at the time. He wasn't the "Best in the World" yet; he was the skinny kid from the indies that the office didn't quite "get." Both of his cash-ins were successful, though. He took out Edge the first time and Jeff Hardy the second. That second one was the turning point—it’s what turned him into the elite heel that eventually gave us the Pipebomb.
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And now, Seth Rollins has joined him. In June 2025, Rollins scaled that ladder and grabbed his second briefcase. It feels different this time. He’s already a legend. He doesn't need the briefcase to be a main-eventer, but having it makes him the most dangerous person on the roster.
What Most People Get Wrong About the Briefcase
There’s this idea that winning Money in the Bank is a guaranteed championship. It’s not. The success rate is high—around 80%—but that 20% of failure is where the real drama lives.
Take Naomi, the 2025 Women’s winner. She’s a veteran. She’s "The Glow." But the pressure of holding that contract is real. You’re expected to be at every show. You’re expected to tease a cash-in every time the champion breathes heavily. If you hold it too long, the fans turn on you (looking at you, Carmella, at 287 days). if you cash in too fast, it feels rushed.
It’s a balancing act that most wrestlers actually find terrifying.
Every Money in the Bank Winner (2005-2025)
If you're looking for the full lineage, it's a wild ride through WWE history. You’ve got legends, you’ve got "what-if" stories, and you’ve got Otis.
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The early years were dominated by the mid-carders trying to break through. Edge, Rob Van Dam, Mr. Kennedy (who lost his briefcase to Edge in a match), and CM Punk. Then the "Big Names" started winning. John Cena, Randy Orton, Brock Lesnar. When Brock won in 2019, he wasn't even in the match. He just walked out at the end, climbed the ladder, and left. People were furious. But that’s the point, isn't it?
The women's division got its own match in 2017. Carmella won the first (with help from James Ellsworth, which was a whole thing). Since then, we’ve seen Alexa Bliss, Bayley, Asuka, Nikki A.S.H., Liv Morgan, Iyo Sky, Tiffany Stratton, and now Naomi. The women’s cash-ins have actually been way more successful than the men’s lately. They usually happen fast. Bliss and Bayley cashed in on the same night they won.
Actionable Insights for the Next Season
If you're following the road to the next ladder match, watch the "quiet" wrestlers. WWE loves to use the briefcase to test the waters with someone who isn't quite at the top yet.
Keep an eye on the "failed" cash-ins. They usually signal a massive character shift. When Drew McIntyre lost his 2024 cash-in, it turned his obsession with CM Punk into something much darker. The briefcase is a prop, sure, but it's also a psychological weight.
Watch the champions, not the winners. The best cash-ins happen when the champion is at their most vulnerable—not just physically, but narratively. If a champion just finished a long, emotional feud, that's when the "I'm cashing in" music is most likely to hit.
Next Steps for Fans:
- Review the 2025 Match: Go back and watch the Rollins win at the Toronto event; the "Fireball" spot is legitimately insane.
- Track the Days: Start a countdown for Naomi and Seth. The longer they hold it, the more the tension builds.
- Check the Stats: Look at the history of "Same Night" cash-ins versus "Long Holds." Usually, the longer someone holds the briefcase, the more likely they are to actually lose the eventual match.
The briefcase isn't just about money. It's about who has the guts to carry the target on their back for a year. In 2025, that target is squarely on Seth Rollins and Naomi. Let's see if they can actually close the deal.