The Wrestling Hipster: An Indisputable Ranking Of All 14 Money In The Bank Briefcase Cash-Ins

‘The Wrestling Hipster’ is a column dedicated to a deeper, enlightened perspective on professional wrestling for people who think having an opinion about pro wrestling makes you deeper and enlightened. If you’re one of those people who reads the italicized disclaimer, the headline is unnecessarily confrontational on purpose to make people who don’t read italicized disclaimers mad. Do not take his seriously, but obey every word I type.

WWE Money in the Bank 2014 is on Sunday, and because I want your web traffic, here is web content.

The Money in the Bank briefcase was created back in 2005 as an excited, unprecedented way to instantly elevate a superstar and get people talking. Nine years later it’s pro wrestling’s best way to give a championship run to someone who doesn’t deserve it. John Cena’s got the belt. Think ZACK RYDER should be champion? Give Zack a win in a PG prop gimmick match where he doesn’t have to pin anybody, have him pin Cena only after Cena’s been excessively beaten up by wrestlers that actually matter and then NEVER TAKE THE NEW CHAMPION SERIOUSLY BECAUSE HE’S A COWARD. Rinse, repeat. Twice a year if possible. Nobody gets anything out of it, but hey, when Zack Ryder goes back to the indies he’s “former WWE Champion Zack Ryder.”

Note: lol

By my count there have been 14 cash-ins of the briefcase between 2005 and three days before Money in the Bank 2014. You can find 3-to-6 barely-updated lists of cash-ins from Bleacher Report at the top of your google search results for Money in the Bank, or you can read an indisputable, definitive ranking of those moments from the only voice on the Internet that matters: me.

Or Dave Shoemaker. But Shoe’s busy podcasting with Bruno Sammartino and Jesus and I’m sitting at home in my underwear, so here’s mine. Years indicated are the years when they won the briefcase, not necessarily when they cashed it in.

14. 2013 – Damien Sandow cashes in on John Cena (and loses)

In very last place forever is reason number 6 to justify your hatred of John Cena, Damien Sandow cashing in his 2013 Money in the Bank briefcase and failing miserably.

It’s less about Sandow not winning and more about how Sandow didn’t win. Cena had a legit elbow injury. He lost the WWE Championship to Daniel Bryan at SummerSlam and took some time off, which in John Cena language means “miss a two months and immediately win the World Heavyweight Championship in my first match back to apologize to myself for leaving.” Cena wrestled Alberto Del Rio at Hell in a Cell, a match build around Del Rio — a guy who destroys arms FOR A LIVING — destroying Cena’s already injured arm. He mauls it for 20 minutes, leading to Cena being momentarily totally fine and hitting Del Rio with an Attitude Adjustment, a move that requires arm strength. He also hooked the leg with his bad arm.

The next night on Raw, Damien Sandow attacked Cena, relentlessly assaulting the now SUPER injured arm with his Money in the Bank briefcase. He cashed in, then spent several minutes continuing to hurt the arm. He smashed it into the ring post. He tossed Cena into the barricade arm-first. Cena, now severely handicapped and beaten within an inch of his life, became totally fine and Attitude Adjusted Sandow to win. Gutwrenching. Here’s more on that if you have the stomach for it.

13. 2012 – John Cena cashes in on CM Punk (and loses)

See that hilarious picture up top? That’s John Cena winning the Money in the Bank briefcase in 2012, the “worst year of his career.” The year he main-evented WrestleMania against one of the biggest WWE stars ever (The Rock), beat Brock Lesnar, won Money in the Bank and only missed out on winning THE OTHER GUY’s Money in the Bank briefcase at TLC because his girlfriend turned on him. He won the Royal Rumble in January of 2013 and went on to win the WWE Championship from The Rock in another consecutive WrestleMania main-event. But you know, horrible year.

The actual horrible part of the year was his attempt to cash in his briefcase. John was attempting to be noble by announcing the title shot ahead of time, because hell, he’s John Cena. What’s he gonna do, lose? He challenged CM Punk to a championship match at Raw’s 1000th episode and lost, but only by disqualification (Big Show interfered), and only after he’d clearly, cleanly had the match won twice. He had a pinfall win with the ref down following an Attitude Adjustment, and Big Show waited until Punk was about to tap out to the STF before he jumped in.

A briefcase cash-in with a ref bump and a DQ finish leading to a series of follow-up championship matches and him winning the belt anyway. Okay.

12. 2011 – Alberto Del Rio cashes in on CM Punk

Remember the Summer Of Punk? Back in 2011, CM Punk became a megastar with a quasi-shoot promo on Raw that made him a household name. People were talking about him on sports radio, wondering with childlike glee if his actions were part of the show or for realsies. It was followed up with one of the best WWE Championship matches EVER in front of an unforgettable, hot-as-lava crowd at Money in the Bank 2011. Punk won the belt from John Cena, blew a kiss in Vince McMahon’s face and left the company with its most prestigious prize. People look back on that month and a half of Punk like they’re remembering their favorite Christmas.

Do you recall how Punk’s title reign ended? In his next match. With Triple H as the special guest referee.

Punk came back to face (who else) new “also” WWE Champion John Cena. He won and unified those titles, but WHOOPS, in stumbled in Kevin Nash to powerbomb him and let The Least Interesting Man In The World Alberto Del Rio steal the newly-won double-title with a Money in the Bank cash-in. Punk got into a feud with Triple H (which he lost) and Cena easily defeated Del Rio for the championship he barely deserved at the next pay-per-view. The next time somebody tells you to “wait and see” where an angle goes, wait and see a f*cking Wikipedia page and use basic human memory.

11. 2013 – Randy Orton cashes in on Daniel Bryan

Tell me if this sounds familiar: WWE Champion John Cena … okay, it already sounds familiar, but shut up. WWE Champion John Cena elects to face popular up-and-comer Daniel Bryan at SummerSlam. Triple H is the special guest referee. Kevin Nash is … somewhere?

Bryan overcomes the Odds Overcomer and wins the WWE Championship, but WHOOPS, Triple H pedigrees him and lets The Least Interesting Man In The Continental United States Randy Orton steal the newly-won title with a Money in the Bank cash-in. Bryan began feuding with Orton in a series of matches he either lost or had reversed/erased from the history books after he won with no payoff until EIGHT MONTHS LATER when he officially, for-real won the championship. And, uh, then he got his neck broken and had to give up the titles.

Meanwhile, John Cena would return in TWO months to easily defeat Alberto Del Rio for the World Heavyweight Championship. I am not copy and pasting these entries, I swear.

10. 2008 – CM Punk cashes in on Edge

I remember how excited I was for this. Watching it again, it’s still a great moment. CM Punk, a guy smarky wrestling fans believed in but never thought would seriously get a fair shake as a main-eventer in WWE, took advantage of a Batista Bomb, cashed in the Money in the Bank briefcase and defeated Edge with a quick Go To Sleep to win his first World Heavyweight Championship.

Looking back, it loses points for two reasons:

1. It’s a babyface cashing in on a vulnerable heel champion and not really “earning” it. The quick cash-in is sorta built for heels to get an accolade they don’t deserve and (in theory) get heat for it. A guy like Punk taking the easy way out makes him look like a coward.

2. Punk’s reign with the belt was unspectacular and sorta built around the reality of #1 … he DID win the title in a cheap way, and even though he was working hard to prove that he deserved it, he still jumped a guy after a More Important Wrestler did his work for him. That ended at Unforgiven 2008. Punk was scheduled to defend the title in Championship Scramble match against four other guys. He never made it to the match. Randy Orton and Legacy attacked him backstage, punting him and taking him out. Chris Jericho took his place in the match and WON, meaning Punk’s first title reign ended with a sneak attack and he couldn’t even defend himself.

9. 2010 – Jack Swagger cashes in on Chris Jericho

While Punk might’ve been the first example of WWE using Money in the Bank to put a championship belt on a guy they aren’t seriously ready to portray as a champion, Jack Swagger was the greatest.

Swagger won the Money in the Bank ladder match at WrestleMania 26 and tried to cash in on John Cena the following Monday. That didn’t work because he remembered at the last minute that this was John Cena. Instead, he waited a little less than a month and cashed in on World Heavyweight Champion Chris Jericho, taking advantage of an attack from Edge. There you go, I just listed every notable event from Jack Swagger’s World Heavyweight Championship reign.

Swagger eventually lost the strap to Rey Mysterio at Fatal Fourway 2010 in a “Come On, Guys, Enough Of This” match. He wouldn’t sniff main events again until a few years later when Alberto Del Rio was Mexican and they needed an American guy to hate Mexicans.

8. 2007 – Edge cashes in on Undertaker (instead of Mr. Kennedy)

This moment loses points for Michael Cole yelling THAT SICK PIRANHA the entire time. I know I said that thing about babyfaces cashing in in the Punk entry, but hey, it’s the Money in the Bank briefcase. You win it, the ability to jump people from behind at inopportune moments and steal shit is basically the point.

Anyway, the moment GAINS points and sits here in the middle of the list for two reasons. One, because Mr. Kennedy originally won this briefcase at WrestleMania, and thank holy baby Jesus we didn’t have to sit through a Mr. Kennedy title reign. Two, because the early years of Money in the Bank cash-ins were acutely aware of the psychology behind them and knew you either had to be an honorable babyface or an absolutely unforgivable heel to get it over.

If you’re gonna be a heel and cash in, you need the face to be on death’s door. Bottom line. You can’t just have somebody powerbomb then and then walk in and win it. That makes everybody look weak. Here, Undertaker had been in a Last Man Standing match with Batista that ended with neither man being able to answer the 10 count. They decided to settle things a week later on Smackdown with a cage match, but both of them escaped the cage at the same time. Before an already tired-as-balls and bloody Taker could leave the ringside area, Mark Henry showed up and mauled him. Beat him down tremendously and Worlds Strongest Slammed him. THAT’s when Edge showed up to cash in. He tries to pin Taker, but Taker kicks out. DRAMA.

So Edge, being a SICK PIRANHA, spears him and has to pin him AGAIN to get the three. Edge cashes in on the most beaten man in the world and looks like a colossal scumbag. Taker looks like a tough motherf*cker because he went through Hell for a week and STILL almost survived it.

7. 2010 – Kane cashes in on Rey Mysterio

This is probably a little too high, but in my mind it’s the smartest Money in the Bank cash-in ever.

The way things work now, Money in the Bank has its own pay-per-view. There are usually two ladder matches. Classically it’s been one for the WWE Championship and one for the World Heavyweight Championship. In 2014 the titles are unified and the champion’s Abeyance, so one’s for the WWE World Heavyweight Championship and the other’s for a cash-in briefcase. To balance out the shows, WWE puts one match at the top of the show and one at the end.

Back in 2010, Kane was in the show-opening ladder match and won a Money in the Bank briefcase. Somewhere in the middle, Rey Mysterio defeated Jack Swagger to retain the World Heavyweight Championship. Swagger was sore about it and tried to injure Mysterio after the match. Kane jogged down to make the save, saving his baby-sized Sometimes Pal Rey. Kane left, then IMMEDIATELY CAME BACK with a referee and cashed in his briefcase. Mysterio stood there all shocked, but it was brilliant. Why wait to cash in if you’re three times the size of the champ and he’s getting his ass kicked on the same show? Cash in, tombstone, fart, new champion.

I’ve always dug it. If Seth Rollins wins the briefcase at the top of the 2014 show, he should cash it in on the unsuspecting guy leaving it all in the ring to win a ladder match for a championship at the end.

6. 2012 – Dolph Ziggler cashes in on Alberto Del Rio

Maybe the most dramatic cash-in ever, and a subversion of the trope. Babyfaces shouldn’t cash in on helpless heels. But what if nobody wants to cheer for your babyface, and everybody loves your heel?

The crowd noise here tells the story. Ziggler had held on to his Money in the Bank briefcase forever, but now was the moment … Alberto Del Rio had spent months getting his leg torn apart by Jack Swagger and was down to his last ounce of strength. Ziggler pounced, but Del Rio fought back. The way Del Rio continues to avoid pinfalls, get in offense and even lock in his finish was HEART-POUNDING. It’s still effective years later. We wanted bad guy Ziggler and his Team Rocket buddies to win more than ANYTHING because we are HORRIBLE JERKS, and this boring dude who is secretly a legitimate badass kept staving it off. The highlight is the cross armbreaker. From the moment when Del Rio locks it in to the moment when Ziggler escapes it by wrenching the ankle is such an emotional roller coaster.

Look at the looks on AJ and Big E’s faces. Those are OUR faces. It’s a shame that Ziggler’s brain and mouth weren’t ready for the championship scene, but I hope he gets back there sometime soon, because what he does in the ring deserves it.

5. 2010 – The Miz cashes in on Randy Orton

In my brain, this is the definitive Money in the Bank cash-in. Other guys had held the briefcase as a stipulation and a future shot, but Miz was the first guy who made it a thing. He carried it wherever he went, and when he couldn’t carry it, he got his henchman to. He used it as a weapon. By the time he cashed in on Orton, the briefcase had a mold of Daniel Bryan’s face in it.

The story though: Wade Barrett is about to pin Randy Orton and win the WWE Championship. But OH NO here comes the recently-fired John Cena (because John Cena is THE WORST) to interfere and cost Barrett the match. Because that’s what good folks do! Orton barely survives and Cena has a reason to physically leave the arena, so it’s the perfect time for Miz to cash in. Not only is the champ vulnerable, the guy who decides what does and doesn’t happen on the show isn’t around to pop in and ruin it. Miz counters an RKO into the Skull-crushing Finale, becomes the 40th WWE Champion and instills us with the very, very false hope that he’ll continue his talent upswing and be one of the most important and compelling champions of the modern era.

Spoiler alert: Cena gave him a horrifying concussion at WrestleMania and The Rock showed up a few times to make him look like a total piece of shit. Miz has yet to recover from either of those things.

4. 2005 – Edge cashes in on John Cena

The first, and still one of the best.

In 2005, we didn’t know how a Money in the Bank briefcase was gonna work. Edge created and defined the Money in the Bank cash-in by waiting until WWE Champion John Cena had wrestled in an Elimination Chamber match at New Year’s Revolution 2006 to cash in, stealing a quick victory against a bloody opponent and winning a belt that he’d be AWESOME with, but not have really “earned.” At least not in John Cena language. And yes, John Cena has been the WWE Champion forever.

Note: Cena won back the championship three weeks later at the Royal Rumble. Three weeks later.

3. 2009 – CM Punk cashes in on Jeff Hardy

CM Punk won back-to-back Money in the Bank ladder matches in 2008 and 2009. In 2008, he was a plucky babyface cashing in on a heel, taking a shortcut and being more opportunistic and weak about it than anybody wanted to admit. He was treated like a coward chump and lost his title to a backstage attack. In 2009, Punk cashed in on fellow babyface Jeff Hardy at Extreme Rules, moments after a grueling garbage match against Edge. Punk took the easy way out and cashed in in the most opportunistic way he could, only this time it was on purpose.

In a rare example of WWE realizing something they’d done wrong and working to fix it, they relived Punk’s initial cash-in and played it for what it really was … the cheap moment of a guy only in it for himself. This was the beginning of Punk’s heel run, dragging Hardy through the mud for his addictions to drugs and alcohol, chastising the live WWE crowds for glorifying a meth-head f*ck-up and ultimately forming the Straight Edge Society. He’d grow out his hair and his beard to become a confrontational, square Jesus, hypocritically commanding a group of bald jerks because of his “message,” but mostly because of his obsession with power. It’s a character that Punk could play well because it was ACTUALLY HIM, and it carried him through to Money in the Bank 2011, when he could spin that character into history-making gold.

I miss you, Straight Edge CM Punk. I really do.

2. 2011 – Daniel Bryan cashes in on Big Show

The only cash-in that created a character I love more than CM Punk is this one.

Daniel Bryan had been one of the best wrestlers in the world (if not THE best) for about a decade when he found his way into WWE. There, he was treated as a “nerd,” a guy too small, too pale and too bland to be a top level talent. Sure, he could wrestle, but wrestling is the least important part of being a WWE Superstar. You gotta SAY FUNNY STUFF and make WACKY FACES when people get prop vomit sprayed on them. You gotta point at your dick and make JOKEZ.

In 2011, he won the Money in the Bank briefcase and a chance to challenge for the World Heavyweight Championship. Being the good dude he is, he promised to do the right thing and cash in in advance for the next year’s WrestleMania. Not only would he get a shot at the belt, he’d be IN THE MAIN EVENT OF WRESTLEMANIA. It was a great idea. As time passed and opportunities presented themselves, Bryan considered cashing in, but didn’t. He was above it.

At TLC 2011, Big Show ended up unconscious in a pile of chairs. Suddenly, Daniel Bryan’s music hit. He rushed out, pinned an immobile Big Show by doing NOTHING and won his first World Heavyweight Championship. The hypocrisy of what he’d done was pretty heavy … he went back on his word and cashed in at the most opportunistic time that required the least amount of work. To combat this train of thought, Bryan did the only thing he could: he became a delusional, arrogant guy who just pretended that he was doing the right thing. He kept retaining the title unexpectedly, and as he did, he would celebrate victories he didn’t deserve to be celebrating. And he’d do it by throwing his hands up and chanting “yes.”

Three years later, he’d be standing on the announce table again, throwing up his hands and chanting “yes” with a title belt in his hand. Only this time, he’d just won two championships in the main event of WrestleMania 30, and everybody in the arena was on his side.

1. 2006 – Rob Van Dam cashes in on John Cena

If you want a cash-in that created a star, meet Rob Van Dam’s cash-in at One Night Stand 2006, the match that created John Cena.

Granted, John Cena was already John Cena. He was winning championships and beating everybody and main-eventing already. That was gonna happen no matter what. But the Cena we know today — the guy who can’t stop mentioning how some people cheer for him and some don’t and how that’s okay — was born here. Important parts of this match include:

1. Van Dam being the second Money in the Bank winner and the first babyface to win it, meaning he announced his title challenge in advance. He did it well, too, choosing to challenge for the belt in an ECW ring in front of the legit ECW faithful at WWE’s second ECW-themed One Night Stand pay-per-view. Hometown advantage. Home turf. 100% fan loyalty, and when I say “100%” I am not using hyperbole.

2. John Cena’s most baller entrance ever. The guy’s shown up at WrestleMania in a sports car, he’s shown up dressed as a gangster, he’s been played out by a drumline and accompanied by 100 John Cena clones, but his best entrance ever is THIS one, where he puts his head down, holds the WWE Championship above his head and defiantly marches straight through the enemy. Bad. Ass.

3. Cena being forced to truly acknowledge the hatred of the crowd for the first time. Loud “F*CK YOU CENA” chants. That iconic “IF CENA WINS WE RIOT” sign that lives on in insincere parodies to this day. The original sign meant it. Cena throwing his t-shirt to the crowd only to have it be thrown back to him, again and again, forcing him to see and feel and EXPERIENCE the hatred. Cena never “embraced the hate” necessarily, but he sure as hell realized he was standing in front of it with its arms open.

4. Van Dam winning, and being (to date) the only babyface champion to announce his title shot in advance and follow through on it. Easily one of the coolest things Van Dam’s ever done. His title reign ended thanks to a shirtless hotbox that yielded 18 grams of marijuana and five Vicodin and got him arrested, but in the context of what happens on the wrestling show, you can’t get much better than this.

Every time Cena brushes off a problem but has to half-assedly acknowledge it because it’s ruining his point, remember One Night Stand 2006, and the modern WWE ecosystem’s most important Money in the Bank cash-in ever.