The Free Press
It’s been nearly 100 days into the Trump presidency and his administration appears bitterly divided over what to do about Iran. The Secretary of State was not present for the negotiations between the mullahs’ diplomats and Trump’s personal friend and special envoy, Steve Witkoff. MAGA World influencers have staked out opposing positions on whether to bomb Iran’s nuclear facilities or go for an Obama-style deal.
This battle is at its nastiest inside the Pentagon, where the restrainer wing of the administration and the more hawkish defense secretary, Pete Hegseth, are now in direct bureaucratic conflict. On Tuesday, Hegseth told Fox News that three recently fired senior officials “are now attempting to leak and sabotage the president’s agenda.”
But is this civil war about foreign policy ideology, or is it about a breach in trust between a cabinet secretary and his closest advisers? Either way, a deep friendship has been torn asunder.
Last week Dan Caldwell, a close friend and senior adviser to Pete Hegseth, was escorted from the building and placed on administrative leave. Within a day, two more senior aides to Hegseth experienced the same fate. Caldwell has said he was fired on Friday.
Caldwell, who has been close with Hegseth for a decade, was supposed to be the James Baker to Hegseth’s George H.W. Bush—a dear friend and fellow operative willing to do bureaucratic combat on his principal’s behalf. Dan Caldwell is now Pete Hegseth’s migraine. In the last 48 hours, Caldwell has posted on X that he and the other two senior aides placed on leave were not even told why they were dismissed. He then went on Tucker Carlson’s show on X and speculated that he was dismissed because of his desire to avoid a “regime change war” with Iran.
Three Pentagon sources close to Hegseth tell The Free Press that the secretary feels personally betrayed by Caldwell. On Monday, Hegseth told reporters that recent negative stories about him were generated by “disgruntled former employees,” a veiled reference to Caldwell, his former aide and ally.
To get a sense of what a turnaround this is for the secretary, consider that Caldwell was entrusted with staffing the Pentagon during the presidential transition. Caldwell was also Hegseth’s proxy in the Signal chats about the Yemen strikes last month. When Republican lawmakers raised questions with Hegseth about Caldwell because of his prior advocacy for reducing America’s military footprint abroad, Hegseth made clear that Caldwell was untouchable, according to two GOP Senate staffers who spoke with The Free Press on background. “Caldwell was a red line,” one of those staffers said. “Hegseth wasn’t going to cut him loose.”
So what caused the break in the Caldwell-Hegseth alliance?
A rumor that Caldwell had photographed secret documents on his phone and leaked them to an NBC reporter spread throughout Washington like a bad cold in the last 48 hours. Three Trump administration officials detailed that accusation without attribution to The Free Press. So far Caldwell has not been charged with any crime, and he said on Tucker Carlson’s show that his personal phone and computer were not confiscated by investigators, nor was he asked to take a polygraph.
“I have not spoken to an NBC reporter while at the Pentagon,” Caldwell told Carlson. “We have not been told as of this recording, one, what we’re being investigated for; two, is there still an investigation?; and three, was there even a real investigation?”
That said, the bond between Hegseth and Caldwell has snapped.
“I’ve been a friend and supporter of Pete Hegseth for a long time and I am just personally devastated by this, it’s just awful and whatnot,” Caldwell told Carlson. “But at the end of the day, putting all this aside, Pete Hegseth needs to be a successful secretary of defense and the entire Department of Defense cannot continue to be consumed by chaos.”
That chaos stems in part from a feud between Caldwell and Hegseth’s former chief of staff, Joe Kasper. Kasper initiated a leak investigation on March 21 after The New York Times reported that Elon Musk was going to receive a classified Pentagon briefing on China war plans.
Part of the problem for Caldwell is that he was responsible for bringing in Pentagon officials who did not work out. For example, he personally vouched for John Ullyot, a former Pentagon spokesman who, on Sunday evening, published a devastating essay in Politico Magazine calling on Trump to fire Hegseth.
Caldwell also hired Michael DiMino to be deputy assistant secretary of defense for Middle East affairs. DiMino had a long track record as an analyst opposing Trump’s first-term policies on Iran, such as imposing maximum economic pressure on their regime through sanctions.
Now it appears that Caldwell and his network are at war against their former boss, Hegseth. At the end of his interview with Carlson, Caldwell let slip that MAGA bête noir and former Obama national security adviser Susan Rice is still on the Defense Policy Board. “That doesn’t mean she can go into the building and get access to whatever she wants, but it means she works with DoD employees and has access to them, and she still has the credential.”
