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EditorialMoney in the Bank Power Rankings: Top 5 Worst to Hold the...

Money in the Bank Power Rankings: Top 5 Worst to Hold the Briefcase

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Previously, the top five best Superstars to have won the Money in the Bank briefcase were profiled. Now, it’s time to turn things upside down and talk about the bottom five on that list—aka, the top five worst.

These Superstars had a guaranteed title shot at any given moment they could choose. It was virtually set in stone they would capture a world title as it was served to them on a silver platter. However, for one reason or another, they completely squandered the opportunity.

Obviously, this isn’t inherently their individual faults. WWE Creative and management set them up for failure in most of these situations. Nevertheless, here are the five worst WWE Superstars who completely botched Money in the Bank as of this moment.

5) Mr. Kennedy

With the “best” part of this rundown, the criteria was to do something memorable while holding the briefcase, successfully cash in to win the title, do it in a fun way and then sustain yourself afterward while hopefully leveling up to the main event and staying there.

Kennedy was unable to do any of those things.

He started off well, saying he would wait to cash in until WrestleMania. That was an intriguing way to go about things and could have had some serious potential. Then, Undertaker suffered an injury and WWE needed to pull the trigger on Kennedy winning the title ahead of time.

Unfortunately, Kennedy also got hurt. The call was made to switch the briefcase over to Edge and hastily have him switch brands and win the title instead.

Sadly, Kennedy wasn’t injured enough that took him out as long as they had thought. If they had known that ahead of time, he likely could have won the title, dawdled a bit, and had an actual run with the belt. His entire career probably would have turned out differently.

Instead, he never reached that level. Every subsequent time WWE seemed ready to strap the rocket to him, he suffered an injury or some other setback. It’s as if the universe said “stop trying; it’s not going to happen” to him.

He’s the first to lose the briefcase, failed to cash in, and fail to have any upward momentum or sustainability.

4) Damien Sandow

Poor Damien Sandow had a lot of great things going for him, but might have been specifically set up to fail.

While Kennedy had the briefcase taken from him, he didn’t actually lose a cash-in. John Cena would use his title shot in advance and fail to win the title, but he won the match by disqualification. Sandow, on the other hand, didn’t get such a distinction.

Rather, he was made to look like a loser while carrying the briefcase. Many fans thought this was a bait-and-switch tactic and he’d win the title. At least that would offset some of the unnecessary damage done to his credibility, right?

Nope. He failed his cash-in. Despite having the advantages and being able to pick his spot, he lost. They simply got it out of the way prior to unifying the two titles between Cena and Randy Orton.

He may or may not have been a sacrificial lamb from the start. I’m inclined to believe it wasn’t the plan, but their whole idea was “Give it to Sandow and we’ll figure it out later, maybe.” That probably evolved into “Who cares? It’ll be funny if he loses and a first time ever scenario. If he can’t bounce back from that, he didn’t deserve to win it in the first place anyway.”

Sandow never bounced back. He had his moments here and there, like with the Mizdow character, but this is what killed his chances of reaching the main event scene.

It’s likely he would have had a better career had he not won Money in the Bank.

3) Baron Corbin

You’d think WWE would learn their lesson from the Sandow situation. Then, Baron Corbin’s run with the briefcase comes along.

They took one of the biggest guys on the roster—someone who was young enough and shown enough promise that he could have reached the main event without this—and decided his tough guy bad ass Lone Wolf no-nonsense character that was squashing people needed a colorful briefcase, a series of humiliations and a failed cash-in.

At the time, I remember thinking “They probably think his subsequent feud with Cena is going to make up for this and that’s what this will have been all about.” Then, that feud didn’t even properly happen!

For absolutely no reason, Corbin held this briefcase, did nothing with it, lost, and had to rebuild himself. Even worse than Sandow, there weren’t any character upgrades along the way. He did nothing to separate himself like Sandow did with personalizing the briefcase, and it wasn’t even worth a laugh. All it did was hurt his credibility and force him to take several steps backward.

This was the first true 100% waste of the Money in the Bank and a sign that maybe WWE just didn’t care anymore.

2) Braun Strowman

How do you take a guy as big as The Monster Among Men, give him the briefcase, set him up for a Hell in a Cell match and then have Brock Lesnar cause a no-contest in a No Disqualification scenario by beating him down with his own briefcase?

There are many instances where WWE shamefully prioritizes the wrong person because they have tunnel vision. Once in a while, they are so heavily focused on one thing that they will purposely sacrifice other things just to slightly nudge that along. Lesnar at this time was that wrongful priority.

It did far more harm to Strowman for this to happen than any benefit that Lesnar gained. Basically, The Beast Incarnate went from a level 100 to a level 100.1. Strowman, meanwhile, went from an 80 to a 60, rather than a 100. He looked like a joke.

Had it not been for COVID and Roman Reigns pulling out of WrestleMania 36, there’s a good chance Strowman never would have won the world title. Instances like this and the Crown Jewel fiasco where they once again humbled the Mountain of a Man in favor of Lesnar proved not even the Money in the Bank briefcase or a size advantage or a match without disqualifications could save someone if they actively wanted to make a joke out of the cash-in.

1) Otis

Speaking of jokes, that’s all the Otis experiment was. While we haven’t gotten 100% confirmation about this, the writing’s on the wall. Vince McMahon thought Otis was funny, figured giving him the briefcase would get a chuckle, had no idea what to actually do beyond that initial moment and didn’t care enough to think of an alternative.

Then, after a few weeks, it became clear it wasn’t as funny anymore. They waited around, not having any ideas of what to do, hoping something would fall into their laps and solve the problem for them.

Eventually, instead of putting in the work to sort out a trajectory, they just gave up. Otis split from Mandy Rose, lost the briefcase to The Miz, Tucker turned on Otis and the two of them never feuded, and the Blue Collar Solid babyface became a heel.

The entirety of Otis as Mr. Money in the Bank can be summed up as “He won it as a gag. Then, basically disappeared until 160 days later, when he lost it and they acted like he never won it in the first place.”

Otis hasn’t recovered. In fact, Otis has fallen down the totem pole since then.

Which five would you pick? Drop your thoughts in the comments!

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