In the wake of Clash at the Castle, WWE Superstars and fans alike have already shifted their focus toward Money in the Bank on July 6. Monday's Raw saw Jey Uso and Iyo Sky became the first to qualify for the men's and women's ladder matches, respectively. Additional qualifiers will determine the rest of both fields in the coming weeks on the main roster.

Capturing the contract guarantees the winner a shot at any championship of their choosing for up to one year. In the past, the concept has been responsible for catapulting careers and giving various promising prospects their first big break as well as their first top title. There have been some stellar cash-ins over the years, but the time spent holding the briefcase is of equal importance.

Only an elite few have managed to stand out and benefit from being in possession of the contract before ultimately cashing it in. There was an extended period where Money in the Bank lost a fair amount of its luster due to various victors not amounting to much and being booked poorly. Last year's Mr.

and Ms. Money in the Bank—Damian Priest and Iyo Sky—bucked the trend and successfully breathed new life into the gimmick. In the near-20 years since MITB's inception, these are the five winners who have had the best runs with the briefcase.

WWE finally introduced a Money in the Bank ladder match for the female stars of SmackDown in 2017, a logical step in the ever-expanding Women's Evolution. They put together a quality matchup, but it was.