WASHINGTON (AP) — Donald Trump touts his transformation of the U.S. Supreme Court as one of his presidency’s greatest accomplishments. Now his legal and political future may lie in the hands of the court he pushed to the right.

With three Trump-appointed justices leading a conservative majority, the court is being thrust into the middle of two cases carrying enormous political implications just weeks before the first votes in the Iowa caucuses. The outcomes of the legal fights could dictate whether the Republican presidential primary front-runner stands trial over his efforts to overturn the 2020 election and whether he has a shot to retake to the White House next November.

“The Supreme Court now is really in a sticky wicket, of historical proportions, of constitutional dimensions, to a degree that I don’t think we’ve ever really seen before,” said Steve Vladeck, a law professor at the University of Texas at Austin.

Trump’s lawyers plan to ask the Supreme Court to overturn a decision Tuesday barring him from Colorado’s ballot under Section 3 of the 14th Amendment, which prohibits anyone who swore an oath to support the Constitution and then “engaged in insurrection” against it from holding office. The Colorado Supreme Court ruling is the first time in history the provision has been used to try to prohibit someone from running for the presidency.

“It’s a political mess the Supreme Court may have a hard time avoiding,” said Michael Gerhardt, a University of North Carolina law professor.

It comes as the justices are separately weighing a request from special counsel Jack Smith to take up and rule quickly on whether Trump can be prosecuted on charges he plotted to overturn the 2020 election results. Prosecutors are hoping the justices will act swiftly to answer whether Trump is immune from prosecution in order to prevent delays that could push the trial — currently scheduled to begin on March 4 — until after next year’s presidential election. Trump has denied any wrongdoing in the case.

The three justices appointed by Trump — Neil Gorsuch, Brett Kavanaugh and Amy Coney Barrett — were among more than 230 federal judges installed under Trump as part of a GOP push to transform the ideological leanings of the bench. His impact on the high court has been seen in rulings rescinding the five-decade-old constitutional right to abortion, setting new standards for evaluating guns laws and striking down affirmative action in college admissions.

“This is a court that is already a lightning rod in our contemporary political discourse. A court that is viewed quite skeptically by a large swath of the American electorate,” Vladeck said. But he added, “It’s also a court that has not bent over backwards for Trump.”

For example, in January 2022, the high court rebuffed Trump’s attempt to withhold presidential documents sought by the congressional committee investigating the Jan. 6 insurrection. The justices also allowed Trump’s tax returns to be handed over to a congressional committee after his refusal to release them touched off a yearslong legal fight.

The Supreme Court was also thrust into the middle of a presidential election more than 20 years ago, in the razor-thin contest between Al Gore and George W. Bush. In 2000, the justices ruled 5-4 to stop a state court-ordered recount of the vote in Florida, a ruling that effectively settled the election in favor of Bush since neither candidate could muster an Electoral College majority without Florida.

But that case came after the votes were cast. And in 2023, “the general political instability in the United States makes the situation now much more precarious,” wrote Rick Hasen, an election-law expert and professor at the UCLA School of Law, on the Election Law Blog.

It’s far from certain that the Supreme Court will decide now to take up Trump’s immunity claims in the election interference case, which were rejected by the trial court judge in a ruling that declared the office of the president “does not confer a lifelong ‘get-out-of-jail-free’ pass.” Smith is asking the Supreme Court to bypass the federal appeals court in Washington, which has expedited its own review of the decision. So the Supreme Court may wait to get involved until after the appeals court judges hear the case.

Trump’s lawyers urged the Supreme Court on Wednesday not to intervene before the appeals court rules, writing that the case “presents momentous, historic questions” that require careful consideration.

The Colorado Supreme Court put its decision on hold until Jan. 4, or until the U.S. Supreme Court rules on the case. Colorado officials say the issue must be settled by Jan. 5, the deadline for the state to print its presidential primary ballots. Mario Nicolais, one of the Colorado attorneys on the case, said the “Supreme Court can move just as fast as it wants, and if they want to hear this before Jan. 5 they can.”

It’s possible the high court will try to dodge the issue and not decide the merits of the Colorado case. Gerhardt said the justices may say that the matter is left to the states or Congress. Section 3 of the 14th Amendment says: “Congress may by a vote of two-thirds of each House” undo the disqualification of someone found to have “engaged in insurrection.”

“It would be like kicking the hornet’s nest for the court to get into the merits of this,” Gerhardt said. “It’s a political hot potato. And the court generally tries to avoid taking on sort of hot-button issues that are political by nature ... And the easier route for the court is to just say ‘somebody else has got the responsibility, not us.’”

But the Supreme Court may feel compelled to answer the issues at the heart of the case now.

“There’ll be a lot of political instability if we go through a whole election season not knowing if one of two major candidates is disqualified from serving,” Hasen said. “It’s hard to fathom the kind of world we’re living in, where not only a serious candidate, but a leading candidate, of one of the political parties is in so much legal jeopardy.”

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Richer reported from Boston. Associated Press reporters Nicholas Riccardi and Brittany Peterson in Denver contributed.