What Insurance Would the Roy Family Actually Need?

The Roys ran a global media empire, fought over a billion-dollar estate, and made catastrophic decisions at every turn. Beneath the private jets and hostile takeovers was a family with some of the most complex — and most neglected — insurance planning needs on television.

Succession is one of the greatest shows in television history — a brutal, darkly funny portrait of a family destroying itself over money, power, and the desperate need for a father's approval. It is also, from a financial planning perspective, a four-season masterclass in what happens when ultra-wealthy people fail to plan.

The Roys had every resource imaginable. What they conspicuously lacked was any coherent succession plan — financial, operational, or otherwise. Let's talk about what a real advisor would have recommended.

Logan Roy — The Patriarch Who Planned Nothing

Logan Roy built a global media empire from nothing. He was brilliant, ruthless, and in control of everything — right up until he wasn't. His death mid-flight in Season 4 is the pivot point the entire series builds toward, and it exposes what he never did: create a clear, binding succession plan for Waystar Royco or his personal estate.

A funded, irrevocable estate plan. Logan's estate was worth billions. Without meticulous planning, estate taxes alone could have forced asset liquidation. An irrevocable life insurance trust (ILIT) — holding a large permanent life insurance policy — is the standard tool for providing liquidity to cover estate taxes without dismantling the business. Logan either didn't have one or didn't execute it cleanly enough to matter.

A buy-sell agreement with clear triggering events. What happens to Waystar when Logan dies? Who buys whom out, at what price, funded by what? The chaos of Seasons 3 and 4 — the GoJo deal, the family infighting, the board maneuvering — is what happens when these agreements don't exist or aren't enforced.

Long-term care planning. Logan's health declined visibly across the series. A man of his wealth had private medical care — but the cognitive and physical decline that made him increasingly erratic also made him vulnerable in ways that proper planning could have addressed. A durable power of attorney, a healthcare directive, and a clear incapacity plan would have protected both him and the company from decisions made in compromised states.

Kendall Roy — The One Who Wanted It Most

Kendall is brilliant, self-destructive, and perpetually one bad decision away from either running the company or losing everything. He has children, significant personal wealth, a history of addiction, and a lifestyle that creates real financial and legal exposure.

Life insurance structured around his children. Kendall has two kids with Rava. His personal wealth is real, but it's also entangled in family dynamics, legal disputes, and a media empire in flux. A substantial life insurance policy — held outside his estate in a trust — ensures his children's financial security regardless of what happens to Waystar or the Roy family fortune.

Estate planning that accounts for his volatility. Kendall's financial situation swings wildly. An estate plan built for his peak net worth may look very different after a leveraged buyout goes sideways. He needs documents that are flexible enough to reflect his actual situation — and a trustee who isn't a family member with their own agenda.

Siobhan Roy — The One Who Married Wrong

Shiv is sharp, politically astute, and consistently underestimated by everyone around her — including herself. Her marriage to Tom Wambsgans is one of the show's central tensions, and by the end it's clear their financial lives are deeply intertwined in ways neither of them planned carefully.

A prenuptial agreement. Shiv's wealth dwarfed Tom's at the time of their marriage. A properly structured prenup would have protected her assets in the event of divorce, which their relationship clearly was heading toward. The absence of one creates enormous complexity when things unravel.

Life insurance and estate planning that reflects her actual role. By the finale, Shiv is carrying Tom's child and newly aligned with GoJo's future. Whatever her financial path looks like, she needs an estate plan and life insurance structure that protects her child — independent of the Roy family dynamics and Tom's own trajectory.

Roman Roy — The One Who Walked Away

Roman is the most honest Roy — painfully, brutally self-aware about his own limitations in a way none of his siblings are. He ends the series walking away from everything, which in financial planning terms means: he has significant personal wealth and no clear plan for what to do with it.

A wealth plan built for someone who doesn't care about legacy. Roman has no children, no spouse, no apparent desire to build something lasting. His financial planning looks very different from his siblings' — focused on asset protection and personal income rather than generational wealth transfer.

Long-term care planning. Ironically, Roman — who ends up alone and unmoored — is the Roy most likely to need a long-term care plan. No children to advocate for him, no clear family structure. A long-term care policy and a durable healthcare directive are more important for someone in his position than almost anyone else in the family.

The Real Takeaway

The entire premise of Succession — four seasons of chaos, betrayal, and heartbreak — rests on one man's failure to plan clearly for what would happen after he was gone. Logan Roy had every resource available to him. He just never did the work.

You don't need a billion-dollar media empire to face the same underlying challenge. Every family has a Logan — someone whose death or incapacity will reshape everyone else's future. The question is whether the planning is in place before that moment arrives.

Life insurance. Long-term care. A clear estate plan. These aren't things for the ultra-wealthy to worry about — they're for anyone who has people depending on them and assets worth protecting.

Don't be Logan. We can help you do the work now — and we promise it involves significantly less family drama.