Supreme Court Predictions 2026: Upcoming Rulings & Retirement Odds

The Supreme Court's 2025-2026 term includes several cases that could reshape American law on executive power, technology regulation, and individual rights. Prediction markets are pricing outcomes on the most consequential rulings, as well as the perennial question of whether any justices will retire. Here is what real-money markets tell us about SCOTUS in 2026.

Key Cases on the 2025-2026 Docket

The current term features several landmark cases with major implications. Prediction markets have formed on the outcomes of the most significant ones.

Executive Power Cases

Multiple cases this term test the boundaries of executive authority, particularly regarding administrative actions and federal agency power. Following the landmark Chevron reversal in 2024, courts have been rethinking how much deference to give federal agencies.

Technology and Free Speech

Several cases involve the intersection of technology platforms, free speech, and government regulation:

• Social media content moderation: Can states require platforms to host certain content? Markets assign 42% probability to the Court siding with states
• AI-generated content and liability: Early cases are reaching appellate courts, with SCOTUS potentially taking up AI liability questions in the next term
• Government communication with tech platforms: Post-Murthy v. Missouri, new cases test the boundaries of government jawboning

Retirement Watch: Will Any Justice Step Down?

Every Supreme Court term brings speculation about retirements. With a 6-3 conservative majority and a Republican president, conservative justices have a strategic window to retire and ensure like-minded replacements.

Markets assign 25% probability to at least one justice retiring in 2026. Thomas and Alito are the most likely candidates, given their ages and the strategic incentive to retire under a Republican president who would appoint their replacements. Sotomayor faces pressure from some Democrats to retire, but at 72 she is younger than the conservative justices most likely to step down, and she would be replaced by a Trump appointee regardless.

What a Retirement Would Mean

If Thomas or Alito retires, the 6-3 conservative majority remains intact since Trump would appoint a conservative replacement. The significance would be in the age of the replacement: swapping a 76-year-old justice for someone in their 40s or 50s would lock in the conservative majority for decades.

If a liberal justice like Sotomayor were to leave (only 5% odds), it would give Trump the opportunity to create a 7-2 conservative supermajority, the most lopsided Court in modern history.

The Court's Impact on 2026 Politics

Supreme Court decisions will directly impact the 2026 midterm elections. Rulings on executive power, immigration, and social issues could energize voters on both sides. The Court's approval rating, which dropped to historic lows after the Dobbs decision, has partially recovered but remains a politically charged topic.

Prediction markets suggest that SCOTUS rulings will play a moderate role in 2026 midterms, with 35% probability that a major ruling becomes a top-three campaign issue for either party.

Longer-Term Court Composition Predictions

Looking beyond 2026, prediction markets offer insights into the Court's future:

• Conservative majority persists through 2030: 88% probability
• At least two new justices by 2028: 35% probability
• Court expansion legislation introduced: 45% probability (but only 8% probability of passage)

FAQ: Supreme Court Predictions 2026

Will any Supreme Court justice retire in 2026?

Prediction markets assign 25% probability. Thomas (76) and Alito (76) are the most likely candidates, with strategic incentive to retire under a Republican president. However, both have shown no public indication of plans to step down.

What are the most important cases this term?

Executive power cases testing the limits of presidential authority are the most significant, particularly in the post-Chevron landscape. Cases involving technology regulation and social media content moderation are also consequential.

Could the Supreme Court be expanded?

Court expansion legislation has been introduced before but has never advanced. Markets assign only 8% probability to court expansion actually passing, though 45% odds that the legislation is at least introduced again.