What will the Supreme Court look like at the end of Trump's term?

Step 1: Current Baseline As of March 24, 2026, the Supreme Court already has exactly 6 Republican-appointed justices and 3 Democratic-appointed justices. This is the target configuration for YES resolution.

Step 2: Critical Insight - Asymmetric Risk This bet has asymmetric risk:

• If ANY of the 3 liberal justices (Sotomayor, Kagan, Jackson) vacates before January 20, 2029 → Trump appoints a conservative replacement → 7-2 conservative majority → NO resolution
• If ANY of the 6 conservative justices vacates → Trump appoints another conservative → maintains 6-3 balance → YES resolution still possible

Therefore, the bet resolves YES if and only if ALL THREE liberal justices remain on the bench for 34 months (March 2026 to January 2029).

Step 3: Actuarial Risk Assessment

Justice Sotomayor (age 71, Type 1 diabetes):

• PRIMARY risk factor for NO resolution
• Has chronic health condition that increases mortality/disability risk
• Explicitly refused retirement pressure in late 2024, signaling strong ideological commitment to remain
• Actuarial risk over 34 months for someone her age with diabetes: ~15-25%

Justice Kagan (age 65):

• No known severe health issues
• Well below average Supreme Court retirement age
• Actuarial risk over 34 months: ~3-5%

Justice Jackson (age 55):

• Youngest justice, no known health issues
• Actuarial risk over 34 months: ~1-2%

Step 4: Combined Probability Calculation

Using independence assumption for actuarial events:

• P(Sotomayor survives) ≈ 0.80 (80%)
• P(Kagan survives) ≈ 0.96 (96%)
• P(Jackson survives) ≈ 0.985 (98.5%)

P(YES) = P(all three survive) = 0.80 × 0.96 × 0.985 ≈ 0.757 (75.7%)

Step 5: Adjustments

Downward adjustments:

• Unknown health information: Justices' actual health status is private; Sotomayor could have undisclosed conditions
• Unexpected events: accidents, acute illness, family emergencies forcing retirement
• 34 months is a meaningful time horizon for septuagenarians with chronic conditions

Upward adjustments:

• Sotomayor's recent, explicit refusal to retire shows strong commitment and suggests she believes her health is adequate
• Supreme Court justices have exceptional healthcare access
• Ideological motivation: Sotomayor knows retirement under Trump would devastate the liberal wing for a generation
• Historical precedent: Justices rarely retire during opposing-party presidencies (Ginsburg precedent)

Step 6: Final Estimate

Balancing these factors, I estimate P(YES) = 72%, slightly below the pure actuarial calculation but above the market's 67.5%. The difference reflects:

1. Sotomayor's demonstrated commitment to remaining on the bench
2. Superior healthcare access for justices
3. Strong ideological incentives preventing voluntary retirement

Step 7: Market Comparison

Market: 67.5% YES My estimate: 72% YES Difference: +4.5 percentage points

The market appears to be pricing in slightly higher Sotomayor health risk (~28% chance she vacates) versus my estimate (~23% chance). This modest difference could reflect:

• Market participants weighting actuarial tables more heavily
• Concern about undisclosed health issues
• General pessimism about septuagenarians with chronic conditions over 34-month horizons

SLIGHT EDGE FOR YES: My estimate of 72% versus market's 67.5% suggests the market is slightly underpricing the probability of YES resolution. The 4.5 percentage point difference represents modest value, though not compelling given uncertainty levels.

The market appears to be pricing higher Sotomayor health risk (~32.5% she vacates) than I estimate (~28% combined risk across all three liberal justices). Key reasons for my higher estimate:

1. Demonstrated commitment: Sotomayor's fierce 2024 resistance to retirement pressure is recent, well-documented evidence of her intention and self-assessed health adequacy
2. Ideological incentives: She knows retirement under Trump would create a 7-2 conservative supermajority for decades
3. Healthcare advantage: Supreme Court justices have exceptional medical access and monitoring
4. Actuarial considerations: Even for 71-year-old with diabetes, 34-month survival probability is reasonably high (75-85%)

However, the edge is NOT strong enough to warrant high conviction because:

• Health events are inherently unpredictable
• Private health information could justify market's caution
• 34 months is a meaningful time horizon for uncertainty
• Market participants may have superior actuarial modeling

Recommendation: Modest value on YES at 67.5%, but position size should be small due to high uncertainty and single-point-of-failure risk (Sotomayor health). This is not a strong inefficiency—more of a marginal edge based on weighing ideological commitment factors slightly more than pure actuarial risk.