Olbermann vs. Trump #18: The 100 Cringeworthiest Trump Moments
14:13
Olbermann vs. Trump #18: The 100 Cringeworthiest Trump Moments
183K viewsNov 1, 2020
YouTubeKeith Olbermann
NEWEST EVIDENCE TRUMP IS NOT LOYAL TO THE UNITED STATES - 9.10.26 | Countdown with Keith Olbermann
57:07
NEWEST EVIDENCE TRUMP IS NOT LOYAL TO THE UNITED STATES - 9.10.26 | Countdown with Keith Olbermann
117.9K views1 month ago
YouTubeKeith Olbermann
TOP MAGA MAGAZINE HEADLINE: "TRUMP IS LOSING HIS MIND" - 4.23.26 | Countdown with Keith Olbermann
54:16
TOP MAGA MAGAZINE HEADLINE: "TRUMP IS LOSING HIS MIND" - 4.23.26 | Countdown with Keith Olbermann
79.3K views6 months ago
YouTubeKeith Olbermann
TRUMP CALLS AMERICA "STUPID" - 4.2.26 | Countdown with Keith Olbermann
48:50
TRUMP CALLS AMERICA "STUPID" - 4.2.26 | Countdown with Keith Olbermann
63.7K views6 months ago
YouTubeKeith Olbermann
TRUMP BECOMES THE FIRST U.S. PRESIDENT TO LOSE A WAR! - 8.6.26 | Countdown with Keith Olbermann
1:33:06
TRUMP BECOMES THE FIRST U.S. PRESIDENT TO LOSE A WAR! - 8.6.26 | Countdown with Keith Olbermann
150.3K views2 months ago
YouTubeKeith Olbermann
TRUMP DOUBLES DOWN WITH DISTURBING MAKE-OUT IMAGE - 4.16.26 | Countdown with Keith Olbermann
58:34
TRUMP DOUBLES DOWN WITH DISTURBING MAKE-OUT IMAGE - 4.16.26 | Countdown with Keith Olbermann
72.4K views6 months ago
YouTubeKeith Olbermann
EMPEROR TRUMP HAS NO CLOTHES - AND NO CLUE ON IRAN - 4.20.26 | Countdown with Keith Olbermann
53:54
EMPEROR TRUMP HAS NO CLOTHES - AND NO CLUE ON IRAN - 4.20.26 | Countdown with Keith Olbermann
65K views6 months ago
YouTubeKeith Olbermann
1:36
BREAKING: REPUBLICANS THROW TRUMP OVERBOARD on the all-new Countdown podcast dropping at midnight
36.4K views4 weeks ago
YouTubeKeith Olbermann
1:01:17
TRUMP IS GIVING IRAN $14B WITH WHICH IT CAN TRY TO KILL AMERICANS - 3.23.26 | Keith Olbermann
62.6K views7 months ago
YouTubeKeith Olbermann
1:04:39
BREAKING: REPUBLICANS THROW TRUMP OVERBOARD - 9.24.2026 | Countdown with Keith Olbermann
103.2K views4 weeks ago
YouTubeKeith Olbermann
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