Bayley had a night to remember at WWE's Money In The Bank pay-per-view, as she won the women's MITB Ladder match and immediately cashed-in on the newly-crowned Smackdown women's champion, Charlotte Flair. Always a fan-favorite annual event, Money In The Bank is unique for featuring both a men's and women's Ladder match in which the prize is a briefcase dangling above the ring. Within said briefcase is a contract that allows the match winner a title shot at a time of their choosing. This stipulation has led to many memorable moments over the years and some wrestlers have held the MITB briefcase like a championship belt in its own right.
Since moving from NXT to WWE's main roster, it's perhaps fair to say that Bayley has experienced mixed fortunes. On Triple H's developmental brand, Bayley was a long-reigning champion and incredibly over with fans as the top babyface of the women's division. Despite a brief stint with the Raw women's title and recent tag team success alongside Sasha Banks, Bayley has unfortunately been involved in some of the worst story angles in WWE history and has been booked to lose a lot more than her army of loyal Huggers would like.
However, Money In The Bank 2019 proved to be arguably the best night of Bayley's main roster career. The women's MITB Ladder match kicked off the main portion of the show, immediately hinting at a possible cash-in that same night, and after a typically grueling match involving Ember Moon, Mandy Rose (with Sonya Deville), Nikki Cross, Naomi, Dana Brooke, Natalya and Carmella, the woman standing atop the ladder with briefcase in-hand at the end of the match was Bayley.
A little later came the two title defenses of double-champion Becky Lynch. Immediately after dispatching newcomer Lacey Evans with the Disarm-Her to retain her Raw belt, Becky's second challenger Charlotte Flair arrived to compete for the Smackdown crown. Fatigued from pulling double duty and with Evans running interference, Charlotte bested The Man, leaving fans noticeably disappointed at the prospect of another Charlotte title reign. As the two heels began a post-match beatdown on Lynch, Bayley rushed down the ramp to make the heroic save and after seeing off Flair and Evans, decided to cash-in her briefcase there and then to rip the Smackdown women's title from Charlotte's clutches.
In a night that was marred by somewhat controversial booking on the men's side, Money In The Bank 2019 was certainly a strong showing for the women's division and all the main players came out looking strong. Becky Lynch remains the Raw women's champ, Lacey Evans impressed in her first big singles match, Charlotte picked up a win on the night and Bayley walked out the first female Grand Slam champion. Additionally, the bait-and-switch tease of Charlotte's win riled up fans perfectly and made Bayley's ultimate victory feel all the more special.
Many WWE followers will be hoping that Money In The Bank 2019 proves to be the start of big things for Bayley on the main roster. An ever-popular superstar and one of the company's "four horsewomen," Bayley's in-ring ability and potential as a top talent has never been in question but, like so many others, her strengths haven't always been utilized since leaving NXT. As perhaps the biggest winner coming out of Money In The Bank 2019 however, it feels like WWE may finally be ready to give Bayley the push she deserves.