Of late, President Donald Trump has issued multiple threats to different countries. Which isn’t anything new, considering his past threats to both Greenland and Canada. But is it really such a good idea for Trump to go around threatening other countries, knowing there might be severe consequences to it? This is exactly what author Michael Wolff discussed.
During a new episode of The Daily Beast podcast Inside Trump’s Head, Wolff and his co-host Joanna Coles had a detailed conversation about Trump’s recent actions. Wolff dissected Trump’s most recent threats about sending American troops or ordering bombing missions to Iran.
The president has put himself in a bind in his clash with Iran, according to Michael Wolff.https://t.co/cbJgU6px85
— The Daily Beast (@thedailybeast) February 20, 2026
Wolff reflected on Trump’s threat and claimed that the president has yet again landed himself in a vulnerable position. He described Trump’s position as being caught in a “serious pickle.”
Wolff said, “I mean, he kinda really looks weak — and he’s already backpedaled this quite a bit.” The author then went on to recall the threat to Iran. Recently, Iran took action against protesters, reportedly resulting in the resulting in the loss of thousands of lives. Trump responded to the event in a furious post on his Truth Social account.
Trump encouraged the protesters to continue their protest and “take over their institutions.” Trump urged citizens of Iran to remember the names of the alleged perpetrators because they’re going to “pay a big price.”
🚨JUST IN: President Trump discusses drawing the line in the sand for the Iranian Mullahs.
“Now is the time for Iran to join us on a path that will complete what we’re doing. If they join us, that’ll be great. If they don’t join us, that’ll be great too but it’ll be a very… pic.twitter.com/ADK9NX1yUF
— Commentary Donald J. Trump Posts From Truth Social (@TrumpDailyPosts) February 19, 2026
The president hinted at sending in troops, something Coles mentioned earlier during the conversation with Wolff. In a separate post, Trump claimed that a “huge armada” was heading toward Iran and urged the Iranian government to strike a deal before time runs out for them. This threat has the internet abuzz with speculation, conspiracy theories and one big question: Is the U.S. going to war with Iran?”
For now, the answer is no since the Trump administration has not officially confirmed these allegations.
🇺🇸Donald Trump threatens Iran 🇮🇷
He said – Iran must make a deal. Iran has 10 days to make a deal or “bad things” will happen pic.twitter.com/qyKqUPfJZL
— Ajay Kashyap (@EverythingAjay) February 20, 2026
Trump had promised Iran a “banner of protection” to Iranian protesters, as mentioned by Wolff. Despite threats against the Iranian government and offering to protect the protesters, the U.S. has not yet intervened in the delicate yet serious situation. Wolff said the lack of intervention has left Iranian citizens furious and betrayed over the failed assurance of safety.
Wolff called out Trump’s response to Iran’s dire situation, saying, “They did attack protesters beyond anyone’s imagination. And Trump, what did he do? Nothing.” He also claimed that the threats have only complicated the situation with Iran further.
Wolff concluded his thoughts about Trump’s dilemma, saying, “He can’t back down because then he’s going to look weak. He doesn’t want to go forward because it’s so complicated.”
What will Trump’s next course of action be? Only time will tell.
For now, White House Communications Director Steven Cheung criticized Wolff’s expose about Trump’s alleged vulnerable position in the aftermath of the threats against Iran. Cheung reiterated his thoughts about Wolff being a fraud and accused him of fabricating stories and theories about the president.
Cheung wrote about Wolff on X, “He has a severe and debilitating case of Trump Derangement Syndrome that has rotted his peanut-size brain.” Wolff has yet to respond to Cheung’s statement.
