Which Supreme Court justices will resign during Trump's term?
Samuel Alito is old enough that a departure before January 2029 is plausible, but Supreme Court justices often stay on the bench longer than outsiders expect. I put this below a coin flip and think the market is somewhat too optimistic on a resignation occurring during Trump’s term.
Analysis
Alito will be in his late 70s by the end of Trump’s term, so age alone makes a departure materially possible. Supreme Court justices, however, are not bound by term limits, and absent a clear health issue or a strong personal reason to leave, many remain in office well past the point where retirement would be rational for most other jobs. That means the baseline chance of him leaving is meaningful, but still not something I would treat as the most likely outcome.
The strongest case for Yes is strategic timing: if Alito intends to retire, Trump’s presidency is the most favorable window for a conservative justice to secure a like-minded successor. The strongest case against Yes is that Alito has every incentive to keep serving if he is healthy, and there is no visible indication that he is preparing to step down. Justices also often prefer to wait for the right combination of health, political control, and personal readiness, which can push retirement past the immediate term even when the logic for leaving is obvious.
At 56%, the market looks a bit high to me. I think it is overweighting the combination of Alito’s age and the fact that Trump is in office, while underweighting the historical tendency of justices to stay longer than expected and the absence of any concrete resignation signal. My estimate is closer to the low 40s: a real possibility, but not the most probable outcome.
Arguments
For
- He will be old enough by 2028 that retirement would be a natural and defensible choice.
- Leaving during Trump’s term would maximize the chance of a conservative replacement.
Against
- Justices often serve far longer than observers expect, especially when they remain healthy.
- There is no current sign that Alito wants to leave the Court soon.
Key drivers
- Alito’s age puts him in the range where retirement becomes increasingly plausible over a three-and-a-half-year horizon.
- A Republican presidency creates a strategic incentive to resign before a possible change in the Court’s ideological balance.
- There is no public evidence of imminent retirement, which keeps the baseline probability from rising into clear-favorite territory.
Risk factors
- An unexpected health issue could accelerate a departure well before the term ends.
- Changes in Senate control or the 2028 election could alter the timing calculus and either encourage or discourage retirement.
Scenarios
Best case
Alito chooses to retire while Trump is still president, likely after gauging political conditions and the likelihood of a smooth confirmation.
Most likely
Alito continues serving for now, with retirement possible later in the term but still more likely than not to wait until after this presidential period.
Worst case
He remains on the Court through January 2029, either because he stays healthy and committed or because the political timing never feels right.
More from this day
- cryptoPolymarket3mo
Will Anthropic flip BTC by December 31?
AI2%MKT77%Edge-75HypedAnthropic flipping Bitcoin by the end of 2026 looks extraordinarily unlikely. The valuation gap is so large that it would likely require a once-in-a-generation private funding event for Anthropic and a major Bitcoin drawdown at the same time.
- pop culturePolymarketEnded
"Spider-Man: Brand New Day" total domestic gross by August 31? (Higher Strikes)
AI25%MKT84%Edge-59HypedMy read is that Spider-Man: Brand New Day is more likely to finish above 900M domestically by August 31 than below it. I put the chance of less than 900M at about 25%, because the film is already so far along that only an unusually sharp slowdown would keep it under the line.
- PoliticsKalshi2y
Which agencies will Trump eliminate?
AI74%MKT30%Edge+44Hidden GemUSAID already looks functionally dismantled, with most staff, projects, and operational authority stripped away. The main uncertainty is whether the market resolves on de facto elimination or requires formal statutory abolition, but I still see a Yes outcome as more likely than not.