100 Worst WWE Matches Ever - 2 - "Donald Trump" vs. "Rosie O'Donnell"
Raw, 8th January 2007
“Good evening, my name is Vince McMahon. Throughout the annals of history, there have been matches that have changed the course of sports entertainment. Bruno Sammartino vs Superstar Billy Graham, Hulk Hogan vs Andre the Giant, Stone Cold Steve Austin vs. The Rock. Tonight will be no different. After all the bickering, finally tonight the match America has been waiting for: Donald Trump vs. Rosie O’Donnell. It’s the Brash Billionaire vs. the left leaning lesbian. It’s all tonight, on Monday Night Raw.” - Vince McMahon
Make no mistake, this match was always awful. Everyone hated it at the time - from the live crowd to online reception in the immediate aftermath. I have never seen anyone jump to this segment’s defence, and any publicity it garnered was simply to make reference to how stupid, childish, and unfunny it was.
Beyond that, knowing what we know about Vince McMahon and Donald Trump as people, especially in recent years, makes the whole glorification of these two narcissistic billionaires gross and uncomfortable. Back in 2007, I knew that Vince was a weirdo creep, but my naïve 16-year-old mind thought that was the limit to his misdeeds. Little did I know that him being a total weirdo extended far beyond that to a genuine sexual predator, trafficker, abuser, among a litany of other crimes that would be too cumbersome to list. Yet, amazingly, he pales in comparison to his good friend. Donald Trump, for better or worse, is one of the world’s most prominent and influential figures of the last century. His effect on global modern politics as we know it cannot and should not be understated. As a teen, I thought he was just a businessman with terrible hair who happened to be the obnoxious host of a far inferior version of the Apprentice. In reality, the future 45th President of the United States is also a well documented creep, a self-confessed sexual predator, and wannabe fascist dictator who orchestrated a riot in an attempt to overturn the outcome of a Presidential election. I cannot believe I am typing this out. At this point it goes without saying, but if you’re looking for impartiality in this review, I’m afraid it’s not something I can deliver due to the divisive nature of the people we are discussing.
I almost didn’t want to dedicate any time to these two assholes. However, out of respect for the reader, how much you’ve stuck with me and enjoyed my series, and the desire to see me in great, unimaginable pain - I will continue like the hero I am. And not only continue, but in a true demonstration of my commitment to the cause, I watched the entirety of this wretched episode of Raw.
Make no mistake, this is one of the worst episodes of wrestling television this side of WCW.
It also explains why this otherwise innocuous 6 minute match ranks as high as number 2. After all, we aren’t talking about anything with high expectations or a main event Wrestlemania level match, nor even did it take place on a $40 pay-per-view. However, it was very heavily promoted. The entirety of the first hour of Raw is dedicated to advertising this at the top of the hour. It is the only previously advertised match prior to the show airing, and was the centrepiece of all promotional material in the build up.
As a non-American viewer of wrestling, sometimes there are cultural references in wrestling that are lost on me. As someone whose only exposure to Rosie O’Donnell came from wrestling and Donald Trump himself, it’s difficult for me to give an informed opinion and naturally my own biases will come into play. However, I will try as best I can to summarise how we got to this point.
In late 2006, after a controversy involving Miss USA, Rosie called out Trump for being an amoral asshole, a creep, and a man who had bankrupted multiple businesses. Trump, famously a guy that doesn’t like hearing the truth, responded by calling Rosie a loser, fat, and threatened to sue her. See, Rosie O’Donnell happens to be a combination of many things that rich white conservatives hate. A plus-sized, left leaning lesbian woman who wasn’t afraid to speak her mind. This back and forth garnered a lot of attention, and Vince McMahon - who had already planted the seeds to the upcoming Donald Trump feud a week earlier - decided to pounce on this for a cheap buzz.
Amazingly, this real-life feud is still going today, and therefore in a twisted sense you could describe it as one of the longest running wrestling feuds ever. Both still throw jabs repeatedly even some 17+ years later. Trump even famously referenced his feud with Rosie O’Donnell during the 2015 Republican Primary debates. Think about how deranged this situation is. This petty feud between two celebrities was referenced nearly 10 years later on a platform that was used to help elect the President of the United States. The most recent comment I could find from Trump on Rosie was in October 2023 where he managed to word vomit a criticism of China, Forbes Magazine, Stormy Daniels, Rosie O’Donnell, the Attorney General of New York, and Joe Biden all in one single barely comprehensible post to Truth Social. He might have commented more recently than that, but I have no desire to delve any deeper, lest I give myself a fucking aneurysm.
I am sorry you had to read this.
In the first of several backstage skits on this episode, Vince McMahon introduces us to Rosie O’Donnell (portrayed by independent wrestler Kiley Mclean who would never wrestle again after this, hopefully out of sheer shame). Vince got her a plus sized couch (because she’s fat, you see), and got her a cake in the shape of a whale (because she’s fat, you see). Vince then says that there’s an old expression “you are what you eat” (because she’s fat, you see). Rosie says she’s going to devour Trump like she’s devouring her precious Fudgey the Whale (because she’s fat, you see).
In the second segment, Rosie finds herself wandering into the Diva’s locker room with an ice cream sandwich and a devious look on her face (because she’s fat and a lesbian, you see). There she meets up with Candice and Maria, and pervs on both their cleavage (because she’s a lesbian, you see). She then drops a bunch of photographs and asks Maria to pick them up, so she can check her out some more (because she’s a lesbian you see).
Backstage, the Donald is getting sprayed with copious amounts of hairspray (because he has funny hair, you see). The Donald is portrayed by famous thrower of chairs, Ace Steel. Despite helping train the likes of CM Punk, Colt Cabana, and Lita; and despite being a part of literally my favourite match of the century (ROH vs CZW Cage of Death); Ace Steel’s two most famous contributions to wrestling are portraying Donald Trump on an episode of Raw, and taking a bite out of Kenny Omega during Brawl Out.
This is all without mentioning the fact that during every preceding match, JR and King are busy hyping the upcoming Trump and Rosie confrontation.
I decided to check something out of sheer morbid curiosity, and to prove a point. Throughout the first hour of this episode of Raw, here’s the breakdown of every reference and joke made about the two celebrities. This should help demonstrate the level of comedy we’re dealing with. I could maybe consider having some room in my heart to forgive this segment if the humour was in any way imaginative, but it is quite literally the same 4 lowest-hanging-fruit jokes hammered repeatedly into your brain. This isn’t comedy, it’s not satire, it’s not even a fucking SNL skit.
Rosie O’Donnell is a leftist: 2
Rosie O’Donnell is a lesbian: 9
Rosie O’Donnell is fat: 23
Donald Trump has strange hair: 9
Onto the actual “match”, and Vince McMahon comes out to make the official introductions: “Weighing god knows what … the double chinned diva in … all her lesbionic fury, Rosie O’Donnell”. Her entrance music is a tuba because of course it is.
It’s painfully obvious this is all put together by one of Donald Trump’s best friends. Looking at the breakdown above proves the vitriol to Rosie feels so much more personal and mean spirited than what Trump receives. They clearly weren’t allowed to say anything remotely personal about Trump. Even as far as the pre-match graphic has the standard toothy smile of Donald Trump and the most unflattering picture of Rosie. The only negative comments about Trump on the whole broadcast are about his hair, and they never even say it’s bad - just that it’s unique. The commentators are quick to pimp the Apprentice as a hit TV show, and Vince hypes up his friend as a legitimate billionaire and master businessman. If this was a genuine attempt to embarrass both of these people, rather than a mere hit piece against Rosie O’Donnell, then there is more than enough ammunition they could have used against Trump on a personal and professional level. Hell, the sheer irony that they’re making fun of Rosie O’Donnell’s weight when she’s feuding with Donald Trump of all people is absolutely ridiculous. That is, unless you are dumb enough to believe his own self-billed height and weight …
Before the match, Rosie and Donald get into a shouting contest, with Trump saying “stay off the hair, porky”. Rosie says she’s going to “sue you for everything you have so I can buy a large pizza!” The fans boo immediately. If you watch this on the WWE Network, you aren’t going to appreciate the fan response because it is edited. The only positive to the WWE network edit is you can hear the trash talking between the two. On the original broadcast, you cannot hear a thing because they are swamped by a never-ending barrage of boos, and a massive “boring” chant immediately. In all my years watching wrestling, I can’t remember a “boring” chant at the very start of a match. I feel you have to watch the original broadcast to appreciate the disdain the St Louis crowd shows for this.
https://www.dailymotion.com/video/x5tcer
Rosie has cramps in her stomach, but there just happens to be Fudgey the Whale on the announce table for no other reason than to bash your stupid brain over the head with this juvenile joke until you too have the humour and nuance of the same people that wrote this shit. They lock up and Rosie immediately puts Donald on his ass, as JR comments that Rosie “has a size and strength advantage”.
Throughout, Trump is constantly adjusting his hair between every single move (I didn’t count every instance of this in my breakdown above). You see, because Trump has unique hair. Ace Steel takes every opportunity to fit in as many fat jokes as he can. “Come on, fatty, King get the BBQ sauce”. After overpowering Trump once more, Rosie starts doing Hulk Hogan poses, to which Lawler comments “she’s mocking the Hulk but she’s more like the bulk”.
Rosie tries to bash Trump’s head into the turnbuckle, but it has no effect. He follows up with a pair of hairbutts. After a few more poses, we get the loudest TNA chant ever heard outside of the Impact Zone. All the while, Vince McMahon sits at ringside with a gormless look on his face, probably wondering why the fans were not finding this the funniest thing in the world. Do you have any idea how bad your product has to be to get TNA chants on your show in 2007?
The look of a man with a front row seat to hear the fans chant for his biggest competitor.
Trump goes for a slam, but there’s too much weight and Rosie falls on top of him for a near fall. Even the network version fails to drown out the boos here.
Trump grabs Rosie’s whale cake and proudly declares “I’m gonna fire this broad right now. Come on fatty, come on fatty, come on fatty”. He smashes Rosie with Fudgey as the fans chant “we want wrestling”. A second rope hairbutt picks up the win for the Donald.
Just a complete and utter disaster. Outside of the sheer embarrassment that Vince McMahon must have felt at ringside as the fans chant for a rival wrestling company, there are zero redeeming qualities about this. This is worse than King of the Ring 2000, because at least Patterson and Brisco sort of made sense in the storyline. While it was on a pay-per-view, nobody bought the show for Patterson and Brisco (if you did, seek help). People paid money to go to an episode of Raw dedicated entirely to this segment. Not only that, this was an early step in promoting the biggest match of this year’s Wrestlemania.
The Trump and McMahon feud would end up being a money making machine for WWE. The Battle of the Billionaires was the driving force behind Wrestlemania 23 being the most purchased WWE pay-per-view of all time when it aired. It currently ranks as the number 2 all time, only behind Wrestlemania 28 (John Cena vs. The Rock - Once in a Lifetime), and with the death of pay-per-view that is a distinction it will likely hold forever. Despite this, the feud started with one of wrestling’s most infamously terrible segments.
In truth, at the very start of the process I always had it in my mind that the race to the number 1 spot was between two matches. There were others I briefly considered, and of course I rewatched everything to be sure I was happy with my rankings. But this was one of two matches that I felt had a very legitimate shot to take the top spot. We’ll dig deeper into why I reached my final ranking in the next entry, but make no mistake, this is one of the worst pieces of media ever devised and deserves every bit of hatred, ridicule, and criticism it still receives to this day.
Up Next - No teaser. Just this…
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