Kennedy Curse Strikes Again: Has The Family Office Failed?

Three generations after JFK the family legacy keeps killing people. Hyannis overdose proves none of the grandkids are safe.

Another college student with everything to live for has died, apparently a drug overdose. People are quick to dredge up a history of depression and suicidal thought.

They’re also quick to dredge up the Kennedy family curse. This particular student was Saoirse Kennedy Hill. She was found dead in the six-acre family compound in Cape Cod.

And that’s enough to reset the long counter of tragedies that have struck the dynasty that grew up around that particular section of beach over the generations.

We’re more than half a century out from the assassination of Saoirse’s grandfather Bobby and all the other names keep circulating. Great-uncle Teddy felt a “curse” hanging over the family even then. 

After that, you’ve got John Jr. and all the other strokes, overdoses, crashes, heart attacks, accidents and suicides. The toll keeps rising high enough to make people ask where the family advisors are.

In this kind of situation, it’s easy to look for institutions to blame. Shouldn’t someone work a little harder to at least check in on the heirs and make sure everyone in the dynasty is thriving?

Maybe the family offices of tomorrow will come up with systems for doing that. But even then, odds are good that they won’t catch the next Kennedy who falls through the cracks.

Finding fault, planning better

First and foremost, a lot of people around the family will blame themselves. These kinds of situations are always magnets for regret. 

Saoirse was staying with grandmother Ethel in the compound. It isn’t clear if anyone else in the family was there or what the outside staffing situation is like.

Ethel is 91. Hyannis may be the bustling hub of Cape Cod but that doesn’t really mean much. She’s a long way out if something goes wrong.

I’m hoping someone in the family was within emergency contact range. Maybe that was Saoirse’s role before the situation shifted. It’s too early to say and that’s not really the point of this exercise.

The point is that when these things play out on property associated with the family and its non-profit affiliates, the family office needs to be involved, for liability purposes if nothing else.

If any of the grandkids had brought a friend home who overdosed or hurt someone, the advisors would have needed to clean up the scandal. Smart advisors hire capable property management teams and arm them with procedures to prevent it when possible.

Those on-site personnel would also monitor family members’ health for referral to a pre-approved local medical contact if anything goes wrong. You don’t want signs to go unrecognized.

Every fixed location in the family’s orbit needs an emergency protocol to cover these situations. People need to be trained to follow it and empowered to take action. It becomes part of the property manual and the staffing cycle.

The property manual becomes the de facto contract that guests and relatives need to obey: a slightly more rigorous version of the old “rules for the beach house” that assigned bedrooms, chores and parking.

When needed, family authority figures can be brought into the loop to enforce compliance. If the party gets too wild or the kids start showing signs of drifting over the edge, it escalates to the parents.

And while nobody is going to tell Ethel Kennedy what to do, she should always have a caretaker or at least a companion checking in. Anyone can break a hip and suffer while waiting for the ambulance.

Risk makes it all worth living

For that matter, there’s a lot of value in preparing emergency plans for every dynastic household even when they’re at home. If you’re already building systems for the vacation home, the places the family inhabits the rest of the year have got to be at least as secure.

This probably means a minimum electronic monitoring package for every separate household. Seniors and at-risk youth are good candidates for extra, up to and including wearable health trackers. 

Talk to their doctors about what they need and what would help. You are talking to their doctors, right? While the records will always fall on that side of the professional curtain, too few advisors incorporate family physicians into their team structure or even emergency CRM. 

It’s always going to be a balancing act between keeping secrets and calling for help. In an ideal world, you’ll spell out optional levels of surveillance for each family member in the account paperwork. They can opt in or out.

And when it’s a trust that pays the bills, the trust can mandate voluntary compliance as part of what it takes to remain a beneficiary in good standing. If the kids don’t like it, they don’t get paid.

Of course they’ll find ways around surveillance just like the seniors do. They’ll still find ways to get into trouble. 

That’s just how life works, whether you have a famous last name or not. Part of being a Kennedy means getting out there and savoring life. 

You’ll die on the ski slopes. You’ll pilot a plane. You’ll get into politics and make powerful enemies. You’ll live alone at the beach house because that’s what you want.

There’s no “Walton Curse” or even a “Disney Curse.” Those families play a more careful game. They live a long time, mostly quietly and always in comfort.

Other families live by different ethics. That’s what a dynastic advisor needs to discover and codify.

A family office serves the institution of the family first. Heirs and even generations come and go, but what the office provides is continuity. Perpetuating that continuity as efficiently as possible means risk management comes first.

The people naturally push against that. But having a system in place for them to push against is better than simply letting them go.

Where the Curse strikes next

At the end of the day, Kennedy is just another name. It’s only when it’s backed up with an estimated $1 billion in interlocking family trusts that we even talk about systems separate from character, free will, ambition and luck.

Figure there are 30 of Joe’s grandkids today and another 70 of Saiorse’s generation, the great-grandkids. That’s 100 individuals, each with their objectives and ultimate mortality ahead.

Some will thrive, some will die young, others will simply drift.

Individually, that’s only about $10 million apiece, which is not enough to really support the kind of comprehensive planning we’ve been talking about. They’d have to make their own rules and plot their own contingencies.

But as a dynastic unit, they add up to something more than statistics. Figure 1 in 50 kids Saoirse’s age would die before age 30. A dynastic plan takes that into account.

Even the early Kennedy generations lost a lot of kids early on. They raised a lot more than they lost. And while $10 million per heir is not world-shaking money, spreading it that many ways ensures that all are comfortable and that the dynastic future is well diversified.

There are probably people available to stay with the older members over the summer and comfort the bereaved when accidents happen. People can step into gaps in the structure.

The planners provide assistance and efficiency. The dynasty of tomorrow will take advantage of technology, managing risk for old and young heirs alike.

Sooner or later, another Kennedy will die and it will probably be noteworthy. A Shriver, a Hill, a Smith: people will mourn. The Curse will strike and another $10 million will roll to the next generation or back into the main family fund for redistribution.

The Kennedy family office seems very hands off. Joe and generations of lawyers didn’t program the trust documents to reward or punish, hinder or heal. That’s the family’s job. And every family suffers along the way, but life is all about how you keep going.


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