President Trump moved on Monday to stack the boards overseeing U.S. military service academies with conservative activists and political allies, including Michael T. Flynn and Walt Nauta, who were charged in connection to earlier investigations of Mr. Trump and his presidential campaign.

Mr. Nauta, a military aide working as a White House valet while Mr. Trump was president, was appointed to the board overseeing the U.S. Naval Academy in Annapolis, Md. Mr. Nauta was charged with aiding Mr. Trump in obstructing the government’s efforts to retrieve a trove of highly sensitive documents that Mr. Trump kept after he left office — one of four criminal cases against Mr. Trump that shadowed him during his presidential campaign last year.

Mr. Flynn, a retired lieutenant general and a national security adviser to Mr. Trump during his first term, was named to the oversight board of the U.S. Military Academy at West Point, in New York. Mr. Flynn twice pleaded guilty to lying to the F.B.I. about his conversations with a Russian diplomat during a wider investigation into contacts between the first Trump presidential campaign and Russian officials. Mr. Trump later pardoned Mr. Flynn.

Other allies of the president appointed to the oversight boards included Charlie Kirk, a conservative activist whose organization aided Mr. Trump in the 2024 election; Dina Powell, a deputy national security adviser to Mr. Trump; Sean Spicer, Mr. Trump’s first White House press secretary; and Maureen Bannon, the daughter of Steve Bannon who helps run his podcast. Mr. Trump also appointed Republican members of Congress and other military veterans to oversee the academies.

Mr. Kirk, who was appointed to the board overseeing the U.S. Air Force Academy in Colorado, had joined other conservatives in assailing the U.S. military leadership before Mr. Trump took office in January, arguing that the armed forces had gone soft under the Biden administration. Soon after the election, he gleefully predicted that Pete Hegseth, now the defense secretary, would “end the wokeification of the U.S. military.”

“He’s going to end the gay story time on battleships, not an exaggeration,” Mr. Kirk said on his talk radio show in November. He added, “The military is not a place for touchy feelings and nonsense, OK? You exist to crush our enemies.”

The president had purged the oversight boards at the U.S. Military Academy, the U.S. Naval Academy and the U.S. Air Force Academy last month, declaring that the institutions had been “infiltrated by Woke Leftist Ideologues.” The Trump administration has carried out a sweeping purge of top officers, diversity initiatives, transgender service members and other policies and personnel that Trump said had made the armed forces “woke.”

Those efforts quickly spread to the U.S. military academies: In February, West Point ordered 12 officially sanctioned clubs for women and ethnic or racial groups to shut down to comply with the Trump administration’s directives on diversity, equity and inclusion. Among them was the Corbin Forum, a group to promote female leaders, founded in 1976 when women were first admitted to West Point.