Manchester by the Sea – A Film About a Trustee

Tough trustee voyage in “Manchester by the Sea”: Award-winning movie also has a lot to say about empowering trust administration


Manchester by the Sea has joined my short list of exceptional trustee movies – that’s my list of excellent films which also provide great insights into the world of trusts. For two others on the list, consider both Citizen Kane and The Descendants.

Part of this film’s appeal admittedly is that trustee, Lee Chandler (Casey Affleck), like Mad Max of the eponymous movie series, is in his own special hell, making his personal redemption through his journey as fiduciary all the sweeter.

So here’s the requisite spoiler alert. Either finish reading this after you go see the film, or use this as a guide as to what to look for.


Lee dutifully travels up from his Boston home to the titled town in order to deal with his brother Joe’s untimely, though not unexpected death.

In the course of performing the various duties – funeral arrangement, communications to the family, etc – Lee goes to Joe’s lawyer to review the will. The lawyer reports that Joe appointed Lee both trustee and guardian for Joe’s 16-year-old son, Patrick (Lucas Hedges). I know you’re wondering – the boy’s non-custodial, divorced mother is not a possibility because of her substance abuse.

Lee is shocked at his fiduciary appointments. The attorney protests that he had assumed Joe had cleared the assignments with Lee. So much for the attorney proactively confirming this essential piece of the transition in advance. 

But here’s one of the narrow exceptions to lining-up one’s fiduciaries in advance: Lee insists he would not have accepted the positions if his brother had asked him.

We know this is true. Lee is crippled by having contributed to the house fire which resulted in the deaths of all three of his young children some years before. We witness his ongoing self-flagellation, including later simple, but devastating scenes in which he carefully packs the frames holding the photos of his deceased children into the bag to bring to Manchester just to set them out again for his personal display in his temporary quarters at Joe’s house.

Since the fire, Lee has shut himself out from all meaningful relationships. Further, he can’t contemplate being responsible for a child again.

And so Lee tries the next best thing: to resign the fiduciary positions for his nephew. But he has no success. He therefore continues his fairly efficient job in taking care of Joe’s final tasks.

Our insight into Lee’s immediately prior life is as an apartment building janitor, emerged in a steady stream of tasks, and engaged, and often enraged, by the sometimes appreciative and sometimes hostile tenants – and bracketed by the occasional drunken fights at a local tavern. He’s fighting a losing battle to cope through repression.

Lee is clearly good at project management and execution in both his present and past worlds – good skills for a trustee! In contrast, Lee’s modest ability to exercise control and aloofness as a janitor is challenged as he’s forced to deal with circumstances around his nephew, whom he clearly cares for.

This solid relationship is demonstrated in the flashback of them fishing, while Patrick is young. And we have the happy ending of the movie, depicted with a view of the two of them once again fishing together. These scenes bracket the demonstrated importance of building the trustee relationship before need. But I’m getting a bit ahead.

With the death of his father, Patrick’s relationship with his uncle, Lee, is understandably stressed. Some of this is caused by both of their inabilities to demonstrate much of the emotions that are seething and consistent with their macho culture. Lee’s non-empathetic communications with his nephew are understandable, but no less counter-productive. And Patrick’s inevitable breakdown is likely more intense and troubling because of it.

In fact, the movie also does a lovely job in highlighting the beneficiary’s arc from indifference to awakening.


Patrick is shown going about his life as usual immediately after his father’s death, including going to school the next day, and making more time with his two girlfriends without the limits that his father had imposed.

Though he accompanies his uncle Lee on some of his tasks, Patrick does not at first invest in the process. And so he sits working his smartphone in the waiting room of the lawyer’s office. On the way back to the car, however, Patrick expresses interest in the details as to his father’s commercial fishing business, and particularly his boat.

The wonderful ensuing dialogue is as follows, though even better with the visuals in the movie as they walk through the cold in search for Lee’s car:

Nephew: What about the boat?

Uncle: We’ll talk to George [father’s trusted employee] about it. There’s no use hanging onto it if no one’s going to use it.

Nephew: I’m going to use it.

Uncle: It’s got to be maintained.

Nephew: I’m maintaining it. I’m going to maintain it.

Uncle: You can’t maintain it by yourself.

Nephew: Why not? It’s my boat now, isn’t it?

Uncle: Because you’re a minor. You can’t take it out alone. And I’m the trustee because I get to make the payments, I get to keep up the inspections.

Nephew: So what does ‘trustee’ mean?

Uncle: It means I’m in charge of handling everything for you until you …

Nephew: Does that mean you’re allowed to sell the boat if I don’t want you to?

Uncle: … turn 18. I don’t know. I’ll definitely consider it.

Nephew: No [expletive] way.

The power of trustee dynamic is especially fraught when it’s unpacked for the first time during the heightened post-mortem emotions.


To Lee’s credit, he does take on meeting Patrick’s desires and requests. This is an all the more impressive achievement, because the path is not clear and is strewn with obstacles. As to the boat, Lee rejects Patrick’s ideas on how to go forward: both continued use while unrepaired as well as securing a repair loan without the means to repay it.

Happily, Lee recognizes an opportunity through the sale of Joe’s extensive firearm collection to provide the necessary funds. This is creative administration at its best: finding the sometimes-not-so-obvious means to empower the beneficiary.

Lee also creatively addresses Patrick’s other desire: to continue living in their home town, which his uncle abandoned after the death of his own children. Lee tries first to find for himself a job in Manchester, but isn’t able to due to the town’s prejudice over his involvement with his children’s deaths.

Faced with the challenge of not being able to stay in the town himself, Lee eventually solves the problem by transferring some, but not all, of his fiduciary responsibilities to George. And so we see a trustee fulfilling his responsibilities to do right by his beneficiary by handing them on to someone else.

Finally, the movie achieves a positive Hollywood ending, even out of this bleak fact pattern, by showing how the entire painful process has moved Lee a bit closer towards his own personal redemption. Lee is now enjoying a positive ongoing relationship, specifically his relationship with Patrick. One step forward is the warm final fishing scene, which echoed the fond memories of the past.

Another step forward into real relationships is Lee’s decision to lease a larger apartment back in Boston to include a room for when Patrick will visit. The dialogue between the two, however, poses a question as to whether Patrick will visit. But Patrick has an appreciation for his uncle’s devastation – Patrick is stopped short by his uncle’s display of the photos of his deceased cousins. An appreciation which we’d expect is likely to grow over Patrick’s maturity.

I have to believe that Patrick will visit his uncle and that Lee’s redemption will continue. After all, those seriously on this fiduciary journey, like Lee Chandler, can’t help but move forward.