Trump Legal Team Weighs 22nd Amendment Loopholes for 2028 Bid

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Donald Trump and his inner circle are reportedly engaging in private discussions about the possibility of a

third term in office, raising constitutional and political questions. Retired Harvard Law professor Alan Dershowitz, a noted constitutional scholar, told Trump that the constitutionality of a third term remains "unclear", according to a report by the Wall Street Journal. The conversation reportedly occurred in the context of Dershowitz's work on a draft book exploring the legal pathways through which Trump could potentially return to the presidency according to a WSJ report.

White House Chief of Staff Susie Wiles recently appeared to contradict those discussions in a Vanity Fair interview, stating that Trump "knows he can't run again." This divergence in public statements has led to speculation about how the administration might attempt to navigate the 22nd Amendment, which limits presidential terms to two as noted in WSJ reporting. The 22nd Amendment, ratified in 1951, explicitly states, "No person shall be elected to the office of the President more than twice."

Dershowitz's proposed scenarios include a situation where the Electoral College members could abstain from voting for Trump in the event of a contested election. If that were to happen, he argues, the election would fall to the U.S. Congress to decide. While the National Constitution Center notes that such abstention is rare in U.S. history, Dershowitz's idea has found some support among Trump allies. Businesswoman and major donor Miriam Adelson, who attended the White House Hanukkah party, reportedly expressed enthusiasm about the concept.

The Legal and Political Challenges

Dershowitz's ideas, while creative, have been met with skepticism by legal scholars. James Sample, a Hofstra University law professor, called the scenario "absurd" but acknowledged one plausible route: if two running mates-such as JD Vance or Donald Trump Jr.-declined to serve and instead resigned immediately after taking office, Trump could become Speaker of the House. As reported by the Wall Street Journal, however, this scenario relies on unprecedented and complex political maneuvering.

The 22nd Amendment is seen as a clear legal barrier, but its interpretation is not without controversy. Legal experts are divided on whether the amendment is self-executing or if a new constitutional amendment would be required to allow a third term. Dershowitz has argued that the language of the amendment is vague enough to allow for alternative interpretations. This legal ambiguity is likely to be tested if Trump seeks to run again, potentially leading to a constitutional crisis or a Supreme Court showdown.

What Analysts Are Watching

The political implications of these discussions are significant. If Trump or his allies attempt to run under a third-term platform, it could deepen the divide in an already polarized electorate. Polls suggest that Trump remains a central figure in the Republican Party, but his viability in a 2028 election is uncertain, especially if his economic agenda does not fully deliver on promised results. In a recent interview, Trump expressed uncertainty about whether his economic policies would be enough to secure Republican gains in the 2026 midterms.

At the same time, legal battles are continuing in unrelated but impactful cases. A federal judge in Boston recently signaled openness to striking down a Trump-era policy on rapid third-country deportations. The policy, which allows for the swift deportation of migrants to countries other than their own, has been challenged on due process grounds. While the Supreme Court has previously paused such rulings, the judge noted that the court's emergency rulings often lack detailed reasoning, creating uncertainty for lower courts according to Reuters reporting.

Another legal development that could affect Trump's political fortunes is the Supreme Court's pending decision on the legality of his tariffs. The court is expected to rule in early 2026 on whether Trump's tariffs, imposed under the International Emergency Economic Powers Act (IEEPA), are lawful. The ruling could have wide-reaching implications for executive power and the separation of powers. If the court rules against the administration, it could limit Trump's ability to use tariffs as a policy tool, potentially affecting his economic agenda's effectiveness.

The Broader Political Landscape

While the Trump administration grapples with these legal and political questions, the broader political landscape is also shifting. Democrats are already identifying competitive seats in Republican-held states such as Arizona and Nevada, with hopes of a "blue wave" in the 2026 midterms. Republicans, meanwhile, are targeting Democratic-held districts in states like New York and Pennsylvania.

The 2025 special elections have shown promise for Democrats, with many of their candidates performing better than expected in districts where Trump won by large margins in 2024. These trends suggest that the 2026 midterms could be more competitive than anticipated. However, the outcome will depend on a range of factors, including the national economic climate, the effectiveness of party messaging, and the extent to which Trump remains a central figure in the Republican coalition.

As these developments unfold, the focus remains on how Trump and his allies will respond to the legal and political challenges of a potential third-term bid. Whether through legal arguments, political strategy, or both, the coming months are likely to reveal more about the feasibility-and risks-of a Trump third term.