Donald Trump remains the only president in U.S. history to have been impeached twice, and he was acquitted in U.S. Senate trials both times. Yet according to MS NOW reporter Kevin Frey, a third impeachment of Trump is a strong possibility if Democrats recapture the U.S. House of Representatives in the 2026 midterm elections — and the party's 2027 impeachment strategy may not stop with the president himself.

Frey, writing in MS NOW (formerly MSNBC), reports that Democrats may receive unlikely assistance from Republicans, including from one of the president's most outspoken critics within his own party.

"If Democrats win control of Congress next year," Frey explains, "they'll be faced with a familiar question: Should they impeach President Donald Trump? But one of the president's most outspoken critics from within his own party has some advice for Democrats: Don't underestimate the power of impeaching Cabinet secretaries. Just last week, Rep. Thomas Massie of Kentucky demonstrated the potential power of impeachment when he introduced a resolution targeting Defense Secretary Pete Hegseth."

Frey adds that after Massie's surprise move, House GOP leaders — who were already sending the House home two weeks early for campaign season — "decided to throw in the towel and leave even sooner rather than allow the vote."

Massie, a Republican with libertarian leanings, has not been afraid to challenge Trump at times — a streak that led Trump to back a congressional primary challenge against him. Having lost that primary, Massie will leave Congress in early January 2027. Still, Frey does not rule out other Republicans joining Democrats in supporting articles of impeachment against Trump or members of his Cabinet in 2027, should Democrats flip the House.

According to Frey, Massie "suggested there's a lesson in the whole mess" and said that "impeaching Cabinet members is highly underrated." The maneuver is rare in practice: the House has impeached only one Cabinet secretary in U.S. history — War Secretary William Belknap in 1876, over bribery allegations — and the Senate acquitted him months later.

"I would think a lot of these Cabinet secretaries are going to get pardons at the end of their tenure — or the end of the president's tenure, at least," Massie told MS NOW. Any such clemency has constitutional limits: Article II grants the president pardon power for federal offenses but expressly excludes "Cases of Impeachment," so it cannot halt the impeachment itself.

Frey reports that Democrats "are ramping up plans for aggressive oversight investigations of the Trump administration, should they win control of Congress in the November elections." Already, however, some Democrats believe their party should go further than merely investigating the president — they want impeachment. That is an avenue the party pursued twice against Trump before, without achieving a successful conviction in the Senate, where a two-thirds majority is required. In the aftermath of those impeachments, Trump used the failed convictions to rally his base, casting himself as a martyr and "playing into their fealty."

"That history is forcing Democrats to weigh not just whether to impeach, but whom to impeach," Frey writes. "The GOP skittishness over defending Hegseth is suggesting an alternative approach, particularly if Democrats focus on Cabinet members who have less political loyalty from Republicans than Trump himself."

The immediate checkpoint is November's midterm elections, which will determine House control for the Congress seated in January 2027 — the same month Massie is set to leave office.