Scott Jennings trips up Miles Taylor during a debate over the war in Iran. Credit: CNN screenshot
One of the most devious appointees during President Trump’s first administration received a much-deserved humiliation ritual at the hands of Scott Jennings on Monday night.
Jennings and ex-DHS appointee Taylor appeared as guests during Monday’s episode of NewsNight on CNN, where the topics discussed included the ongoing DHS shutdown and the war in Iran.
As TGP readers know, Taylor, formerly known as “Anonymous,” leaked classified information and covertly tried to sabotage Trump during his first term.
In 2018, The New York Times ran an op-ed by an “Anonymous” author described as a senior member of the Trump Administration who was covertly working to sabotage the President.
The author of the NY Times’ resistance’ op-ed also penned an anti-Trump tell-all book titled “A Warning.”
When the topic turned to the war in Iran, Taylor ripped Trump for alienating European allies with his strategy and mocked his decision-making.
“They (America’s allies) see a president who doesn’t know what he’s doing, who’s constantly moving the goalposts, whose own staff isn’t even sure what he’s doing,” Taylor said.
Jennings later flipped the script on Taylor with just one excellent question: Do you think Ayatollah Khamenei preferred Obama or Trump as President?
Considering Trump was the one who took out Khamenei, the answer is quite obvious.
But this caught Taylor completely off guard, who could only nervously laugh. Then, Jennings moved in and said, “Probably Obama.”
Seeing no way out of Jennings’s trap, Taylor could only state the obvious (Khamenei is dead), which proved Jennings’s point and destroyed the Anonymous author’s entire argument.
WATCH:
Q: “Do you think the Ayatollah prefers his life under Obama or under Trump?”
Ex-DHS Obama donor Miles Taylor: “The Ayahtolla’s dead.”
Bingo. You heard it here first, folks! pic.twitter.com/6jwpjQsbN8
— Scott Jennings (@ScottJenningsKY) March 24, 2026
JENNINGS: Do you think the Ayatollah prefers his life under Obama or under Trump?
TAYLOR: (chuckles nervously)
JENNINGS: Probably Obama, yes?
TAYLOR: The Ayatollah’s dead!
JENNINGS: There you go! You heard it here first, folks!
The post WATCH: Scott Jennings BURIES Treasonous Former DHS Official Miles Taylor with One Brilliant Question After Taylor Mocks President Trump’s Handling of Iran War appeared first on The Gateway Pundit.