When a Donald Trump-appointed judge delivered a stinging rejection of his effort to put National Guard troops on the ground in Portland, the president had some regrets.

“I wasn’t served well by the people that pick judges,” Trump vented Saturday.

His gripe came four months after he similarly sounded off about the “bad advice” he got from the conservative Federalist Society for his first-term judicial nominations — a reaction to a ruling, backed by a Trump-appointed judge, rejecting his power to impose sweeping tariffs on U.S. trading partners.

“This is something that cannot be forgotten!” he said on Truth Social.

While Trump and his allies have spent all year leveling pointed attacks at Democratic judicial appointees, labeling them rogue insurrectionists and radicals, the president is increasingly facing stark rejections from people he put on the bench — including at least one from his second term.

The brushbacks have come mainly from district judges, who occupy the lowest level of the three-tiered federal judiciary. So far, it’s been a different story among Trump’s three most powerful judicial appointees: Supreme Court Justices Neil Gorsuch, Brett Kavanaugh and Amy Coney Barrett. That troika, along with the high court’s three other conservatives, has handed Trump numerous short-term victories in emergency rulings this year, often lifting injunctions against Trump policies issued by district judges.

The White House leaned into that bottom-line success in a statement to POLITICO that attributed Trump’s defeats to Democratic appointees and sidestepped questions about the defeats dealt by Trump’s own picks.

“The Trump Administration’s policies have been consistently upheld by the Supreme Court as lawful despite an unprecedented number of legal challenges and unlawful lower court rulings from far-left liberal activist judges,” said White House spokesperson Abigail Jackson. “The President will continue implementing the policy agenda that the American people voted for in November and will continue to be vindicated by higher courts when liberal activist judges attempt to intervene.”

Trump allies also emphasize that district court judges tend to require the approval of home-state senators, leading presidents to nominate more moderate picks than they might otherwise in states dominated by the opposing party.

Still, in some cases in which Trump-appointed judges have heard Trump-related cases, they have gone further than simply ruling against his policies. They have delivered sweeping warnings about the expansion of executive power, the erosion of checks and balances and have criticized his attacks on judges writ large.

One Trump appointee rebuked the president and his allies for a “smear” campaign against the judiciary.

“Although some tension between the coordinate branches of government is a hallmark of our constitutional system,” U.S. District Judge Thomas Cullen wrote in a recent ruling, “this concerted effort by the Executive to smear and impugn individual judges who rule against it is both unprecedented and unfortunate.”

Rulings against the administration by Trump-appointed judges have come in some of the most high-profile cases of Trump’s second term. Here’s a look at the most notable examples.

National Guard call-up

U.S. District Judge Karin Immergut, a first-term Trump appointee in Oregon, ruled that Trump’s effort to put National Guard troops in Portland was “untethered” from reality and risked plunging the nation into an unconstitutional form of military rule.

Deporting Guatemalan children

U.S. District Judge Tim Kelly, a first-term appointee in Washington, D.C., rejected the Trump administration’s claim that it was trying to reunite unaccompanied Guatemalan kids with their parents when it abruptly loaded hundreds of children onto buses and planes for a middle-of-the-night deportation effort. That explanation “crumbled like a house of cards,” he wrote, after the Guatemalan government contradicted the claim. Kelly blocked the immediate deportations, saying they appeared to violate the law.

Restricting the AP’s White House access

U.S. District Judge Trevor McFadden said the White House had unconstitutionally evicted the Associated Press from Oval Office events over its refusal to adopt Trump’s “Gulf of America” label. McFadden’s ruling was later put on hold by an appeals court. Notably, Trump has mischaracterized this ruling twice in recent days during public remarks, claiming that McFadden, a first-term appointee, not only sided with his restrictions on the AP but endorsed his relabeling of the Gulf of Mexico. Neither McFadden nor the appeals court reached such a conclusion.

Trump’s tariff power

Few issues are as central to Trump’s economic agenda as his power to levy tariffs at will against U.S. trading partners he claims are ripping off the country. But Timothy Reif, a judge he put on the U.S. Court of International Trade, joined two other judges in ruling that Trump lacked the legal power to impose such sweeping tariffs, a traditionally congressional authority. A federal appeals court later agreed with the panel, and the matter is now pending before the Supreme Court.

Summary deportations under the Alien Enemies Act

Several Trump-appointed judges joined a nationwide legal rebuke of the president and his administration over efforts to abruptly deport Venezuelan nationals using Trump’s wartime authority under the Alien Enemies Act. U.S. District Judge Fernando Rodriguez Jr. was the first to label the effort “unlawful.” Two other first-term Trump appointees, U.S. District Judges John Holcomb and Stephanie Haines, ruled that Trump’s invocation of the Alien Enemies Act was legitimate but that the administration’s effort to speedily deport its targets violated their due process rights.

Returning Daniel Lozano Camargo

Among the targets of Trump’s Alien Enemies Act order was Daniel Lozano Camargo, a Venezuelan man who had been residing in Texas. Unlike others whom the administration abruptly sent to El Salvador under that order, Lozano Camargo was protected by a 2024 settlement requiring the government to resolve his pending asylum claim before deportation could occur. U.S. District Judge Stephanie Gallagher, a first-term Trump appointee in Maryland, ordered the administration to facilitate the man’s return to the United States — following the lead of her colleague on the Maryland bench, Obama appointee Paula Xinis, in the similar case of Kilmar Abrego Garcia.

Mandatory detention of potential deportees

The Trump administration has sought to vastly expand the use of detention for immigrants facing deportation — seeking to deprive bond hearings for all potential deportees, even if they’ve spent decades living in the United States. Dozens of judges have found the abrupt shift illegal, saying the move is potentially subjecting millions of people to being locked up while they fight to remain in the United States. In recent days, several Trump appointees have joined their ranks. They include first-term appointees: Dominic Lanza of Arizona, Rebecca Jennings of the Western District of Kentucky and Eric Tostrud of Minnesota. Kyle Dudek of the Middle District of Florida, whom Trump appointed this term, was confirmed to the bench just two weeks before ruling against the administration.

Targeting the Maryland bench

Cullen’s stinging assessment of Trump and his allies’ attacks on judges came in a remarkable legal attack by the Trump administration against the entire federal district court bench in Maryland. The administration sued the judges there over a blanket policy to delay all urgent deportation cases for 48 hours to give the court a chance to act before litigants were deported. The administration said the rule infringed on executive power to execute immigration laws. But Cullen rejected the administration’s lawsuit as defective and the improper way to seek relief from an administrative process it disagreed with.

Other rejections

U.S. District Judge Dabney Friedrich, another Washington, D.C.-based first-term Trump appointee, has turned down the administration on multiple fronts — including an effort by the Justice Department to use Trump’s pardon of Jan. 6 defendants to cover unrelated crimes. She also granted an injunction requiring the administration to disburse funds it had withheld from the National Endowment for Democracy.

Another first-term Trump appointed judge, Mary McElroy of Rhode Island, repeatedly rebuked the administration in recent weeks for abrupt funding cuts to homelessness programs and public health grants. Last week, she blocked the administration from repurposing $233 million in FEMA grants from blue states over what those states said was punishment for refusing to assist with immigration enforcement.