Corporate-owned life insurance on buy-sell may trigger Connelly valuation effect.
The shareholder buy-sell is funded by corporate-owned life insurance on each shareholder. Under Connelly v. United States, the death benefit can inflate estate-tax valuation of the deceased shareholder's interest without offset for the redemption obligation.
S-corp owns three policies, each $4M face value. Buy-sell obligates redemption at death. Cross-purchase structure was never adopted. Holding has been stable for six years.
Whether a cross-purchase restructure is acceptable to all three shareholders. Current policy cash values and surrender posture. Whether partnership form would be tolerated for tax purposes.
Model a cross-purchase restructure or a partnership-owned structure — projected tax exposure reduction: $1.1M–$1.4M on the senior shareholder's estate.
Labeled Projected. Requires shareholder consent; restructure may take 60–90 days. Citations below link to the buy-sell and policy illustrations reviewed.