The Most Unexpected WWE Superstars Who Won Money in the Bank

Money in the Bank has long been one of WWE’s most thrilling events, offering a mix of high-stakes drama and unpredictable twists. The iconic ladder match guarantees that fans will witness jaw-dropping moments, but sometimes, the winners themselves leave everyone stunned. From underdogs to veterans who seemed past their prime, the competition has seen some surprising champions throughout its history. While some Money in the Bank victories felt like natural progressions for rising stars, others were truly unexpected, leaving fans questioning how certain superstars managed to claim the coveted briefcase.

This highlights the most unexpected WWE Superstars who stunned the WWE Universe by winning Money in the Bank, showcasing the unpredictability and excitement that this match brings to the table. These victories not only altered the course of their careers but also changed the direction of the entire WWE.

1. Jack Swagger (2010) – The Surprising Rookie

In 2010, Jack Swagger’s victory in the Money in the Bank Ladder Match took fans by surprise. At the time, Swagger was still relatively new to the WWE main event scene, having debuted just two years earlier. While he had already shown promise, his character was nowhere near as polished or popular as other superstars like Christian, Kane, or MVP, who were considered the favorites going into the match.

Swagger’s victory marked a huge leap in his career, but it also seemed to defy the typical trajectory of a Money in the Bank winner. Traditionally, the briefcase would go to someone on the verge of stardom, and Swagger, though talented, wasn’t a household name yet. However, the win elevated him to the next level, as he cashed in the briefcase to win the World Heavyweight Championship just months later.

While Swagger’s reign was short-lived, the Money in the Bank win was a pivotal moment in his career. It not only showcased his potential but also proved that WWE was willing to take risks with their storylines and push newer talent, even if it seemed like a long shot at the time.

2. The Miz (2010) – A Victory Against the Odds

The Miz’s victory in the 2010 Money in the Bank match was a moment that no one saw coming. Though he was known for his trash-talking persona and his rise through the ranks on the reality show The Real World, Miz was still considered an outsider by many in the wrestling community. Many fans doubted his abilities as a main-event player, especially when compared to the more established names on the roster at the time.

However, The Miz defied expectations and snatched the Money in the Bank briefcase in 2010, signaling that WWE was ready to take a chance on his meteoric rise. His win at the event was not just a to the audience but also a statement of WWE’s willingness to back a character who had worked hard to prove himself. The Miz cashed in his briefcase on Randy Orton later that year, capturing the WWE Championship, which was one of the most talked-about title wins of the era.

The Miz’s triumph in the Money in the Bank match cemented his status as a main eventer. It marked the beginning of his long and successful run at the top, and the victory gave him the momentum needed to prove his doubters wrong and solidify his place in WWE history.

3. Kane (2010) – The Surprise Veteran

Kane’s victory in the 2010 Money in the Bank match wasn’t as much of a stunned in terms of his talent, but his victory still left many scratching their heads. By the time Kane won the Money in the Bank briefcase, he was already a seasoned veteran in WWE. With over a decade of experience, many fans and analysts were expecting newer, younger talent to take center stage in the match. Yet, it was the Big Red Machine who secured the win in a surprise twist that left everyone wondering what the future would hold.

At the time, Kane was far removed from his peak years as a main eventer, and many believed he was nearing the tail end of his career. So, when he won the briefcase, it was unclear what WWE’s plans were for him. However, Kane’s briefcase victory turned out to be a pivotal moment for his character, and he went on to cash in the briefcase and win the World Heavyweight Championship at the 2010 WWE TLC event, defeating Rey Mysterio in a monstrous showdown.

Kane’s win was a reminder that even veteran superstars, especially those with such a storied career, could still be a threat in the Money in the Bank match. His victory also showed that the ladder match could be used to breathe new life into a character that many thought had already reached his peak.

4. Otis (2020) – The Underdog’s Triumph

Otis’ victory in the 2020 Money in the Bank match is arguably one of the most unexpected wins in the history of the event. As a heavyset and charismatic tag team wrestler with a comedy-driven persona, Otis was far from the type of competitor one would expect to win such a prestigious match. In a lineup that featured more seasoned and technically gifted athletes, including AJ Styles, Daniel Bryan, and King Corbin, Otis seemed like a long shot.

Despite the odds, Otis pulled off a win in the Money in the Bank ladder match, outlasting the more experienced superstars and securing the briefcase in one of the most unique Money in the Bank moments to date. The match itself was held inside WWE’s corporate headquarters, adding an extra layer of intrigue and chaos. However, Otis’ win was even more unexpected considering his storyline leading into the event, which was largely centered around his relationship with Mandy Rose.

Though Otis’ title reign never materialized, and he eventually lost the Money in the Bank briefcase due to a storyline involving The Miz, his victory left a lasting impression. It proved that in WWE, anyone could seize the opportunity, regardless of their size, background, or previous accomplishments. Otis’ win was a reminder that the Money in the Bank match is designed to underdogs and create moments that defy conventional expectations.

These four superstars represent the unpredictable nature of the Money in the Bank match, where anything can happen. While each of their victories was unexpected in its own way, these wins had lasting impacts on their careers and the WWE product as a whole. Whether they were young stars on the rise, established veterans, or underdogs with little to no chance, their victories made them household names and ensured that the Money in the Bank match would continue to surprise audiences for years to come.