When the Supreme Court hears oral argument on Feb. 8 over Colorado’s decision to disqualify Donald Trump from appearing on the 2024 ballot on grounds that he engaged in insurrection and therefore violated part of the 14th Amendment, the odds have got to be in Trump’s favor. There are just so many legal and factual issues that have to be resolved just right for the challengers to Trump’s eligibility to succeed. Trump only has to win on one of the issues and he’s back on the ballot, not just in Colorado, but potentially across the country. Still, a look at Trump’s most recently filed Supreme Court brief shows some odd strategic choices, most notably exposing some weaknesses in his position and revealing the Litigant in Chief as hedging some bets for another potential trip to the Supreme Court one year from now.

To understand the strategic choices made in Trump’s brief on the merits, let’s back up first to what happened in Colorado. A group of Republican voters sued the Colorado secretary of state under provisions of Colorado’s elections code arguing that she had to exclude Trump from the ballot. The voters relied upon Section 3 of the 14th Amendment, which provides that:

No person shall be a Senator or Representative in Congress, or elector of President and Vice-President, or hold any office, civil or military, under the United States, or under any State, who, having previously taken an oath, as a member of Congress, or as an officer of the United States, or as a member of any State legislature, or as an executive or judicial officer of any State, to support the Constitution of the United States, shall have engaged in insurrection or rebellion against the same, or given aid or comfort to the enemies thereof. But Congress may by a vote of two-thirds of each House, remove such disability.

The Colorado voters claimed that Trump engaged in an insurrection by, among other things, encouraging the storming of the U.S. Capitol on Jan. 6, 2021, to stop Congress’ counting of the Electoral College votes that formally declared Trump’s opponent Joe Biden as winner of the 2020 presidential election.

Trump and the Colorado Republican Party entered the case, and the trial court held a five-day trial. The trial court batted aside almost all of Trump’s arguments, including that the First Amendment protected his right to fire up the crowd about the supposedly stolen election just as Congress........

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