'Going to be much harder' for Trump as his Supreme Court leverage collapses: court insider

Donald Trump's remarkable winning streak at the Supreme Court is collapsing. After dominating the high court throughout his first year in office, the president is now facing serious resistance from the justices — and it's only going to get worse.

According to Politico, recent developments paint a grim picture for the Trump administration's legal agenda as he enters his lame duck years. The Court delivered "a stinging defeat over his tariff policy" and Wednesday's oral arguments on his birthright citizenship executive order were so hostile that "another loss may be looming."
Trump's legal dominance during 2025 appeared absolute. The administration won nearly all of the roughly 30 emergency appeals filed with the high court, spanning issues from immigration enforcement to mass federal employee firings to the abrupt termination of billions in federal grants and contracts.
But that winning streak is now visibly fracturing. Beyond the tariff defeat and the likely impending birthright citizenship setback, the Court has already rejected Trump's attempt to use the National Guard to control anti-ICE protests. The perception that "Trump has the court firmly in his pocket" is crumbling.
Legal experts explain what's happening: Trump's legal team was strategically selective.
Roman Martinez, who clerked for Chief Justice John Roberts and Justice Brett Kavanaugh, laid out the reality bluntly: "If you just look at the win-loss tracker, yes, it was pretty good for the administration over much of 2025, but the sample set was not a random selection of cases. It was the set of cases that President Trump's legal team chose to take up to the court. And those lawyers were savvy and selective, choosing to appeal the cases where their position was inherently stronger."
The dynamic is now shifting in a direction that terrifies the Trump legal team. "It's going to be much harder and the administration is going to win some, but they're also going to lose some," Martinez said.
As the Court transitions from fast-moving emergency appeals to more time-intensive regular case proceedings, Trump faces mounting resistance from the justices. The administration will no longer be able to rely on expedited processes that favored quick victories.
Solicitor General John Sauer has publicly acknowledged the looming difficulty. "Who's going to argue all these cases…?" he joked at a judges' conference last September, describing the "terrifying" prospect of full arguments on all the emergency cases in which Trump racked up easy wins during his early months in office.