Worst in the World: "Donald Trump" vs "Rosie O'Donnell"-WWE Monday Night RAW (1/8/2007)

(Special thanks to Otter Empire for suggesting this match. If you'd like to see a match covered on the Worst in the World, leave a comment down below.)

There are a lot of words you can use to describe Vince McMahon. "Subtle" is not one of them. Vince hates paying taxes? He writes a heel tax collector into his show and makes his initials "I.R.S." The Parents Television Council is giving him a hard time because of the violence & sexual content on his shows? He creates a stable full of prudes and calls them "Right to Censor." Hulk Hogan, Randy Savage, and Mean Gene Okerlund decided to head over to WCW? He writes sketches that serve little purpose other than to ridicule them by calling them old and over the hill. The man is not afraid to put his opinions on screen. But at the very least, those were all related to his wrestling show, whether it be the establishing of a regular wrestler or group, or was some old-fashioned mudslinging towards his competition. This? Zero connection whatsoever. Donald Trump vs Rosie O'Donnell from the January 8th, 2007 episode of Monday Night Raw. Donald Trump...versus Rosie O'Donnell...how the fuck did we get here?

Given that he was just the President of the United States two years ago, I probably don't need to go into detail about who Donald Trump is, but prior to that, he was a businessman/reality competition host. Rosie O'Donnell is a comedian & actress who's probably better known for her work as a talk show host on The Rosie O'Donnell Show and The View. Donald Trump and Rosie O'Donnell do not like each other...at all. I'm not entirely sure, but from what I've read, Rosie objected to Trump, who used to own the Miss USA beauty pageant, and how he handled a controversy involving the 2006 Miss USA winner, and since then they've gone back and forth with it. Now, what does any of this have to do with WWE or professional wrestling?

...

Nothing...not a single thing...

Sure, Donald Trump had a prominent role in a WrestleMania 23 storyline, has appeared on Raw a few times, and is a member of the WWE Hall of Fame. And sure, Rosie O'Donnell once gave a 5-year-old boy named Max Friedman a spot on her talk show long before he started going by his full initials. But even then, the wrestling connection to these two is minuscule at best. So, why did Vince McMahon dedicate time on his wrestling show to real-life beef between two people who have just about nothing to do with wrestling? Well, it's actually pretty simple.

Vince McMahon and Donald Trump are friends, or at the very least, occasional business partners. I've already mentioned that Trump has appeared on Raw and WrestleMania, and was inducted into the WWE Hall of Fame. WrestleManias IV and V were billed as being held in Trump Plaza (even though it was actually held down the street in the Atlantic City Convention Hall..I don't know why they did that), and Trump even had a storyline where he purchased Monday Night Raw in 2009 (something that legitimately caused WWE's stock to drop 7% within hours of the announcement.) Vince's wife Linda also donated millions of dollars to Trump's presidential campaign, and when that proved successful, Trump, in turn, nominated Linda as the administrator of the Small Business Administration. So yes, Vince McMahon legitimately booked a glorified skit on his show where someone dressed up as his friend got to fight someone dressed up as someone his friend was feuding with in real life. I understand vanity booking, but this is vanity booking for someone else. Let's get into this...whatever this is.

Before the match, Mr. McMahon makes his way to the ring to do the ring announcing, and if you thought for even one millisecond that maybe, just maybe, this wasn't just shameless pandering to Vince's buddy, just you wait. McMahon announces Rosie at a weight of "God only knows how much", calls her the double-chined diva from The View", and says she's here in all her "lesbianic fury." Holy fuck, this is already awful. Outcomes "Rosie O'Donnell" as an entrance theme featuring plenty of tuba plays because of course it does. My god, what the fuck are we doing? The only saving grace to this segment is that no one on the actual roster outside of Vince had to take part in it. The fake Rosie is portrayed here by Virginia-based independent wrestler Kiley McLean. It doesn't seem like McLean's career was too prevalent, as she only had four recorded matches on Cagematch.net. That does not include this match, as Cagematch didn't bother counting this as a match. The fact that Cagematch will count matches from random Virginia indy shows, but doesn't consider something that had a recorded pinfall on a show that aired on national television does not bode well for how this match will go. Also, just to clarify, the Internet Wrestling Database (profightdb.com) does count this as a match, so I'm counting it as well.

The fake Rosie plays up to the crowd, who are DEAD SILENT for this. And even after that, if you had even the tiniest bit of a feeling that this was anything other than Trump fan fiction, Vince introduces Trump as a billionaire who runs his own empire, and is from the "hit show: The Apprentice." The fake Trump enters with a huge wig and comes out to The Apprentice theme. Or, if you're watching this on Peacock or the WWE Network, he comes out to Royalty-Free Cool Guy Song #4. The fake Trump is portrayed by another independent wrestler in Ace Steel, whose portrayal really just boils down to saying "You're Fired" a lot. Steel would actually sign a WWE Developmental contract ten days after this match but never became a full-time main roster member. He later worked as a coach at the WWE Performance Center, and currently works backstage with All Elite Wrestling. However, Steel might be best known as the man who trained CM Punk and Colt Cabana and was a member of the Second City Saints alongside Punk and Cabana in Ring of Honor. Steel was also in the front row with Cabana at Money in the Bank in 2011 for Punk's match with John Cena.

That's about all the stalling I can do to avoid talking about this match.

Jim Ross and Jerry Lawler don't even wait for the match to start to make fat jokes, with Lawler saying Rosie is keeping her watch on "to remind her when it's time to eat again" before Ross says he can hear her stomach growling. The referee tells Trump and Rosie the rules before the bell rings, only for Rosie to immediately leave the ring so she can eat a Fudgie the Whale cake that is set on the announce table for some reason.

What the fuck are we doing? This is some of the most miserably unfunny, terrible shit WWE has put on their shows. I know it's often said that WWE's writers cater to an audience of one, that being Vince himself, but this literally only caters to two people, that being Vince McMahon & Donald Trump. I can't imagine anybody outside of those two enjoying this.

Rosie gets back in the ring as the crowd starts booing. The two finally lock up, with Rosie getting the better of the exchange by shoving Trump down. They repeat the spot, prompting Trump to take off his jacket. Trump slaps on a headlock, but Rosie fights out and knocks Trump down with a shoulder block. Rosie knocks Trump down with another shoulder block before hitting a Thesz Press. Rosie throws Trump to the ground twice before playing up to the crowd, but Trump fights back with a headbutt, which is extra powerful because he has silly hair, I guess. This has been edited out of the Peacock/WWE Network version, but there are very obvious "TNA" chants around this time. TNA couldn't have asked for better advertising than this match.

Trump goes for the bodyslam, and even though they are roughly the same size, Trump collapses picking Rosie up because DO YOU GET IT!? ROSIE O'DONNELL IS A LARGER WOMAN!? DO YOU GET THE JOKE!? I understand that there are jokes made about Trump in this (specifically his catchphrase and his hair, but those are all things that Trump himself jokes about as well. It really feels like this whole thing is laughing with Trump, but laughing at Rosie. Rosie nearly scores the pinfall off the failed slam, but Trump kicks out at two. The crowd is not happy with that, booing loudly that this match will not fucking end. Rosie attempts to hit the worst splash I have ever seen, but Trump rolls out of the way and out of the ring. Trump grabs the cake from ringside and throws it in Rosie's face. Mercifully, Trump climbs to the second rope and hits a diving headbutt (which Lawler calls a "hairbutt") for the three and the win. Jim Ross then lies to everyone watching this:

"Well, ladies & gentlemen" we're having a little...having some fun tonight."

This was not fun.

The Verdict

An outright and unabashed waste of time. This is the worst kind of segment; one that Vince McMahon, and only Vince McMahon, finds funny. It also falls into the same faults that the Golden Truth vs Breezango does where it just tells the same joke over and over again. What makes this worse is that unlike the majority of the times Vince puts something on TV for his own amusement, this has nothing to do with wrestling. Not even a little bit. I could maybe look past it if the in-ring action was at least decent, but it's not. The actual wrestling is barely involved in this match and takes a big back seat to all the bad comedy. If you consider this a segment, then it's among the worst that have ever taken place on Raw (and that's saying something), and if you consider this a match, it's a nothing match that literally wasted time and provided nothing but unfunny, repetitive jokes. 

The Rankings (Best to Worst)

1. Tommy Dreamer vs Bully Ray-Victory Road 2011
2. Triple H vs Kevin Nash-TLC: Tables, Ladders, and Chairs 2011
3. Rick Rude vs Jake Roberts-WrestleMania IV
4. Too Much vs Al Snow & Head-King of the Ring 1998
5. Brock Lesnar vs Roman Reigns-Greatest Royal Rumble
6. Ernest Miller vs Norman Smiley-Fall Brawl 1998
7. Shane McMahon vs Eric Bischoff-SummerSlam 2003
8. The Tag Team Gauntlet-Extreme Rules 2010
9. The Gimmick Battle Royal-WrestleMania X-Seven
10. Hernandez vs Matt Morgan-Victory Road 2011
11. Randy Orton vs Bray Wyatt-WrestleMania 33
12. Vampiro vs Sting-Great American Bash 2000
13. T&A vs Head Cheese-WrestleMania 2000
14. David Arquette & Diamond Dallas Page vs Jeff Jarrett & Eric Bischoff
15. The Women's Tag Team Turmoil-WrestleMania 37 (Night 1)
16. Triple H vs Sgt. Slaughter-D-Generation X: In Your House
17. Konnan vs One Man Gang-SuperBrawl VI
18. Ultimate Warrior vs Hercules-WrestleMania IV
19. Rick Rude vs Hawk-Clash of the Champions XXV
20. Shelton Benjamin vs Viscera-New Year's Revolution 2006
21. Steve McMichael vs Reggie White-Slamboree 1997
22. Lars Sullivan vs Lucha House Party-Super Showdown 2019
23. Alexa Bliss vs Bayley-Extreme Rules 2017
24. The Tag Team Fatal 4-Way Match-WrestleMania 13
25. The Barbed Wire Christmas Tree Match-TNA iMPACT (12/20/2007)
26. Tag Team Battle Royal-WrestleMania XIV
27. EVIL vs Tomohiro Ishii-Wrestle Kingdom 16 (Day 1)
28. The Chamber of Horrors-Halloween Havoc 1991
29. The Natural Disasters vs Money Inc.-WrestleMania VIII
30. Ivan Koloff vs Paul Jones-Clash of the Champions IV
31. ODB, Taylor Wilde, and Roxxi vs The Kongtourage-Genesis 2009
32. Kazushi Sakuraba & Yuji Nagata vs Daniel & Rolles Gracie-Wrestle Kingdom 8
33. Ivory vs Tori-SummerSlam 1999
34. Giant Baba vs Bulldog Bob Brown-WrestleRock
35. The Reverse Battle Royal-Impact! (10/26/2006)
36. Savio Vega vs Rocky Maivia-In Your House 14: Revenge of the Taker
37. Jerry Blackwell vs Boris Zhukov-SuperClash II
38. Nikita Koloff vs Bobby Eaton-Bunkhouse Stampede
39. Alex Wright vs Steve McMichael-Halloween Havoc 1997
40. The Great Khali vs Kane-WrestleMania 23
41. Savio Vega vs Crush vs Faarooq-Ground Zero: In Your House
42. The Shockmaster vs Awesome/King Kong-Starrcade 1993
43. Total Divas vs Other Divas-Survivor Series 2013
44. The Intercontinental Championship Elimination Chamber-Elimination Chamber 2015
45. The Oddities vs Kaientai-SummerSlam 1998
46. Team RAW vs Team SmackDown Men's Elimination Match-Survivor Series 2017
47. Hulk Hogan vs Sid Justice-WrestleMania VIII
48. Paul Ellering vs Teddy Long-Capital Combat
49. Dusty Rhodes vs Big Boss Man-Saturday Night's Main Event (10/31/1989)
50. Konnan vs Scott Hall-Fall Brawl 1998
51. Damian Priest vs The Miz-WrestleMania Backlash
52. Tyson Tomko vs Stevie Richards-Unforgiven 2004
53. Kane vs The Great Khali-SummerSlam 2009
54. Rick Steiner vs Scott Steiner-Fall Brawl 1998
55. The Extreme Elimination Chamber-December to Dismember 2006
56. Hollywood Hogan vs The Giant-Hog Wild
57. Hollywood Hogan vs The Giant-Souled Out 1997
58. Dustin Rhodes & King Kong vs Awesome Kong & The Equalizer-Battlebowl
59. Finlay & Little Bastard vs The Boogeyman & Little Boogeyman-No Way Out 2007
60. Mr. Anderson vs Rob Van Dam-Victory Road 2011
61. Jake Roberts vs Andre the Giant-WrestleMania V
62. El Gigante vs Nailz-G1 Climax 1994 (Day 1)
63. Yokozuna vs King Mabel-In Your House 4
64. Dusty Rhodes vs The Honky Tonk Man-SummerSlam 1989
65. Sting & Hawk vs Meng & Kurasawa-Clash of the Champions XXXI
66. The Hurt Business vs RETRIBUTION-WWE Monday Night RAW (10/26/2020)
67. Hulk Hogan vs Randy Savage-Uncensored 1998
68. Santino Marella vs Heath Slater-WWE Friday Night SmackDown (9/27/2013)
69. Al Snow vs Big Boss Man-Unforgiven 1999
70. Vince Russo vs Ric Flair-WCW Monday Nitro (6/5/2000)
71. Mickie James vs Ashley-Royal Rumble 2006
72. Antonio Inoki vs The Great Antonio-NJPW Sumo Hall Show (12/8/1977)
73. Christy Hemme vs Big Fat Oily Guy-Against All Odds 2007
74. The Big Show vs Erick Rowan-TLC: Tables, Ladders, Chairs 2014
75. British Bulldog & Jim Neidhart vs The Dancing Fools-Fall Brawl 1998
76. Stevie Ray vs Konnan-World War 3 1998
77. Vampiro vs The KISS Demon-Bash at the Beach 2000
78. Team WCW vs nWo Wolfpac vs nWo Hollywood-Fall Brawl 1998
79. Vampiro vs Oklahoma-Starrcade 1999
80. Big Swole vs Penelope Ford, Rebel, and Dr. Britt Baker, D.M.D.-AEW Dynamite (8/27/2020)
81. Hulk Hogan vs Andre the Giant-WrestleMania III
82. Jinder Mahal vs Randy Orton-Battleground 2017
83. Van Hammer vs Terrance Taylor-Clash of the Champions XVI
84. Junkyard Dog vs Moondog Spot-Wrestling Classic
85. The New Blood Gauntlet-WCW Monday Nitro (6/5/2000)
86. Chris Jericho vs "Goldberg"-Fall Brawl 1998
87. Hulk Hogan vs Kevin Nash-WCW Monday Nitro (1/4/1999)
88. Sting vs Hulk Hogan-Halloween Havoc 1999
89. Hulk Hogan vs Jeff Jarrett-Bash at the Beach 2000
90. Roman Reigns vs The Undertaker-WrestleMania 33
91. The Undertaker vs Goldberg-Super ShowDown 2019
92. Hiroshi Wajima vs Tom Magee-All Japan Pro Wrestling 1988
93. Jim Duggan vs Big Boss Man-Royal Rumble 1990
94. Meng vs Jim Duggan-Uncensored 1995
95. Jim Steele vs The Equalizer-SuperBrawl IV
96. The Golden Truth vs Breezango-Money in the Bank 2016
97. The Undertaker vs Giant González-WrestleMania IX
98. Sting vs Tony Palmore-Battle 7
99. D-Generation X vs Brothers of Destruction-Crown Jewel
100. Wendi Richter vs Leilani Kai-WrestleMania
101. Goldberg vs Brock Lesnar-WrestleMania XX
102. Hornswoggle vs Chavo Guerrero-WWE Monday Night Raw (7/20/2009)
103. Edge vs Triple H vs Vladimir Kozlov-Survivor Series 2008
104. Rosita & Sarita vs Angelina Love & Winter-Victory Road 2011
105. Kevin Sullivan vs Dave Sullivan-SuperBrawl V
106. Steve McMichael vs Brian Adams-Road Wild 1998
107. Scott Hall vs Roddy Piper-SuperBrawl IX
108. Boris Zhukov vs Paul Samson-Beach Brawl
109. Roddy Piper vs Hollywood Hogan-Halloween Havoc 1997
110. Kane vs The Great Khali-Breaking Point
111. Hollywood Hogan & Dennis Rodman vs Diamond Dallas Page & Karl Malone-Bash at the Beach 1998
112. PN News & Bobby Eaton vs Steve Austin & Terrance Taylor-Great American Bash 1991
113. Scott Steiner vs Sid Vicious vs Jeff Jarrett vs Road Warrior Animal-Sin
114. Hollywood Hogan vs Roddy Piper-SuperBrawl 1997
115. The 2015 Royal Rumble Match
116. Kazuchika Okada vs Gedo-New Japan Cup 2020 (Day 2)
117. Batista vs The Great Khali-SummerSlam 2007
118. Sting vs Hollywood Hogan-Starrcade 1997
119.  Sable vs Tori-WrestleMania XV
120. Super Invader vs Todd Champion-WrestleWar 1992
121. Brock Lesnar vs Cain Velasquez-Crown Jewel 2019
122. King Kong Bundy & Jim Neidhart vs Yokozuna & Jake Roberts-Heroes of Wrestling
123. Sid Vicious vs The Nightstalker-Clash of the Champions XIII
124. The 8-Divas Tag Match-Survivor Series 1999
125. The Fabulous Freebirds vs The Renegade Warriors-Halloween Havoc 1990
126. The Knockouts Gauntlet-One Night Only: Live! 2016
127. AJ Styles vs Frank Trigg-No Surrender 2008
128. Rick Rude vs Masahiro Chono-Halloween Havoc 1992
129. Mike Awesome vs Vampiro-Halloween Havoc 2000
130. Bray Wyatt vs John Cena-Extreme Rules 2014
131. Brothers of Destruction vs KroniK-Unforgiven 2001
132. The Miss WrestleMania Battle Royal-WrestleMania 25
133. Mabel vs The Undertaker-King of the Ring 1995
134. Wendi Richter vs The Fabulous Moolah-The Brawl to End it All
135. David Flair vs Kimberly Page-Mayhem 1999
136. The Truth Commission vs The Disciples of Apocolypse-Survivor Series 1997
137. Daffney vs Miss Hancock-Bash at the Beach 2000
138. The Bushwhacker vs The Fabulous Rougeaus-WrestleMania V
139. Randy Orton vs "The Fiend" Bray Wyatt-WrestleMania 37 (Night 2)
140. The Beverly Brothers vs The Bushwhackers-Royal Rumble 1992
141. Savio Vega vs Rocky Maivia-WWF Monday Night Raw (4/14/1997)
142. Teddy Long vs Eric Bischoff-Survivor Series 2005
143. Savio Vega vs Rocky Maivia-WWF Shotgun Saturday Night (1/25/1997)
144. Greg Valentine vs George Steele-Heroes of Wrestling
145. Abdullah the Butcher vs One Man Gang-Heroes of Wrestling
146. Major Gunns vs Miss Hancock-New Blood Rising
147. Vince Russo vs Booker T-WCW Monday Nitro (9/25/2000)
148. Bradshaw & Trish Stratus vs Christopher Nowinski & Jackie Gayda-WWE Monday Night RAW (7/8/2002)
149. Triple H vs Scott Steiner-Royal Rumble 2003
150. Goldberg vs "The Fiend" Bray Wyatt-Super ShowDown 2020
151. Santina Marella vs Vickie & Chavo Guerrero-Extreme Rules 2009
152. Kevin Nash vs Scott Steiner vs Goldberg-New Blood Rising
153. Hollywood Hogan vs The Warrior-Halloween Havoc 1998
154. Mr. T vs Roddy Piper-WrestleMania 2
155. The Royal Family vs Clowns R' Us-Survivor Series 1994
156. The House of Horrors Match-Payback 2017
157. The Blacktop Bully vs Dustin Rhodes-Uncensored 1995
158. Team Dos Caras vs Team El Canek-Leyendas Mexicanas 2017
159. Pat Patterson vs Gerald Brisco-King of the Ring 2000
160. The Wyatt Swamp Fight-The Horror Show at Extreme Rules
161. The Four Doinks vs Team Bigelow-Survivor Series 1993
162. Sting vs Jeff Hardy-Victory Road 2011 
163. Bret Hart vs Mr. McMahon-WrestleMania XVI
164. WarGames 2000: Russo's Revenge-WCW Monday Nitro (9/4/2000)
165. Oz vs Tim Parker-SuperBrawl
166. Brock Lesnar vs Braun Strowman-Crown Jewel 2018
167. Brock Lesnar vs Ricochet-Super ShowDown 2020
168. The Mighty Maccabee vs The Iron Sheik-Maccabiah Mania II: Shekel Slam
169. Van Hammer vs Doug Somers-Halloween Havoc 1991
170. Ultimate Warrior vs Andre the Giant-Saturday Night's Main Event (11/25/1989)
171. Jeff Jarrett vs Sting-Halloween Havoc 2000
172. The Doomsday Cage Match-Uncensored 1996
173. "Donald Trump" vs "Rosie O'Donnell"-WWE Monday Night RAW (1/8/2007)
174. Kane vs The Undertaker-Judgement Day 1998
175. Toru Yano vs Jado-New Japan Cup 2020 (Day 1)
176. Rebel vs Shelly Martinez-One Night Only: Knockouts Knockdown
177. Kaitlyn vs Maxine-NXT (10/19/2010)
178. Sabu vs The Sandman-November to Remember 1997
179. Seth Rollins vs "The Fiend" Bray Wyatt-Hell in a Cell 2019
180. Michael Cole vs Jerry Lawler-WrestleMania XXVII
181. The Bushwhackers vs Iron Sheik & Nikolai Volkoff-Heroes of Wrestling
182. James Storm vs Chris Harris-Lockdown 2007
183. John Laurinaitis vs John Cena-Over the Limit 2012
184. Hulk Hogan vs The Giant-Halloween Havoc 1995
185. Ultimate Warrior vs Goldust-In Your House 7
186. Los Villanos vs Los Psycho Circus-Triplemania XXIII
187. Jenna Morasca vs Sharmell-Victory Road 2009
188. Akira Maeda vs Andre the Giant-NJPW Big Fighter Series 1986 (Day 15)

Thanks for reading! Be sure to share if you enjoyed and leave any suggestions for matches you'd like to see covered in the Worst in the World in the comments. I got the request to cover both of the titular matches from the 2022 Royal Rumble, but since Royal Rumble matches require a pretty lengthy review, I've decided to break with my schedule and split them into two separate posts. So next week, I'll cover the Women's Royal Rumble, and then in two weeks, I'll look at the Men's Royal Rumble. Until then.