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The Lincoln Highway: Let’s Talk About That Ending! (Spoilers)

The Lincoln Highway: Let’s Talk About That Ending! (Spoilers)

This is a spoiler-filled discussion about the ending to The Lincoln Highway. If you haven’t read the novel yet, wait to visit this post until after you finished it.

Welcome to the discussion about The Lincoln Highway! If you’re new to Book Club Chat, I write spoiler-free reviews and spoiler-filled book club questions for each novel I read. But lately, I’ve noticed some books deserve a third article—one dedicated to shocking endings. So please feel free to comment with your thoughts at the end of the article.

The Lincoln Highway is a coming-of-age tale about the transition from teenager to adulthood. Each of the main characters are at a crossroads of sorts and in a way, the Lincoln Highway serves as a getaway from their current, somewhat bleak situation.

Particularly, Emmett and Billy. This is their chance to leave behind Nebraska and its bad memories and try out California. While Billy hopes they can find their mother in San Fransisco (even though she abandoned the family), Emmett believes they can get a fresh start with fixing and then selling houses (the original house flippers).

But Duchess made a mess of everything. Once he steals Emmett’s car and heads up to New York, it completely delays Emmett’s and Billy’s plans.

From there, we follow Emmett and Billy’s journey to regain the car and they meet an interesting cast of characters along the way.

The Ending

Remember, this is spoilers, spoilers, spoilers from here on out! So don’t read this unless you’ve finished the book. Seriously!

Up until about the last 60 pages or so, the story is fairly straightforward coming-of-age tale with vivid imagery of the time period and lots of pondering about the past and what’s next. So the shift in tone during the climax to the ending was pretty shocking.

Emmett finds Woolly dead in his bed from a suicide. He’s distraught but when he sees Duchess, all Duchess cares about his trying to get Woolly’s inheritance that is locked away. This horrifies Emmett and he’s determined for Duchess to finally go to the police to own up to his crimes and that’s when the two get into a fight. Eventually, Emmett knocks out Duchess.

It turns out Woolly did leave each of the friends his money. So the brothers take their share of the money and plan to finally go to California.

But Emmett is concerned that Duchess will try and find them. So he decides to put an unconscious Duchess on a boat with his own share of the money. The boat contains a hole and Emmett stacks stones in order to stop the boat from flooding. However, once Duchess is awake and the money begins to blow away, Duchess shifts the boat to try and get it—causing it to sink and since Duchess can’t swim, he drowns.

We apparently see a flash before Duchess dies that shows the brothers in California, Woolly alive, Sally with a child and Sister Sarah. Clearly this doesn’t represent the future since Woolly is alive but maybe that flash was simply Duchess’ wishes. I’m not sure—what do you think about that scene?

Key Events

While the ending is shocking, there are hints of something more sinister going on earlier in the novel—Duchess’ random act of violence against the taunting cowboy in Morgen and also to Ackerly, the former warren of the juvenile camp. Duchess tries to justify both but it’s undeniable that those were unprovoked actions and the fact he doesn’t see that is pretty disturbing in itself.

And with Emmett, while he did not kill the bully on purpose back in Morgen, it does sound like he has anger issues and only Billy can get him to calm down. Although, who wouldn’t be absolutely furious with Duchess and his behavior, right?

But let’s talk over several key events. First, was this Woolly’s plan all along—to commit suicide and leave his friends his inheritance? I think so. This is why his interactions with his sister seemed to have a farewell component to it. Very sad and tragic.

I have seen people wonder if Duchess had a hand in Woolly’s death—such as ensuring Woolly would get his sister’s medicine bottle (which I don’t think we ever got the name of). So, maybe he didn’t actually kill Woolly but he also didn’t help to prevent the overdose. I think it’s left vague on purpose.

The second event I want to discuss is the fact that Duchess makes it seem like this trip is an effort to get revenge at his father for framing him and sending him to the work camp. But he never does come into contact with his father—although it seems like he does try. I was disappointed they never had an interaction and that really didn’t go anywhere.

Reading the story from Duchess’ first-person perspective caused the reader to try to sympathize with him but soon it became apparent that not only was he a liar but he’s also a dangerous person. While Duchess probably thought of himself as a hero, he was the villain, in the end. I don’t feel he was misunderstood—I believe his actions were loud and clear.

Emmett’s Motivations

And so let’s talk about the big twist—Emmett leaving Duchess in the boat. I’ve reread it a couple times and I don’t believe Emmett purposely killed Duchess. I know some feel that way but I just don’t think that was the author’s intention. I feel Emmett was truly concerned that Duchess would find him and Billy and continue to cause havoc so he had to delay Duchess.

But at the same time, I feel that Emmett didn’t care what happened to Duchess. He knows that Duchess can’t swim and he did just enough to provide some safety but it was up to Duchess to ensure that he could get back to shore. Potentially, Emmett laid the groundwork for Duchess to have to choose between the money or survival. This line Emmett thinks before driving away is significant:

“Having come fifteen hundred miles in the wrong direction, on the verge of traveling three thousand more, Emmett believed that the power within him was new in nature, that no one but he could know what he was capable of, and he only has just begun to know it himself.”

How I take this is after Emmett murdered that bully, he really worked to contain his anger but Duchess’ behavior left him no choice. If Emmett didn’t stop Duchess, Emmett believes that Duchess would again get in the way of their plans. So Emmett will not get pushed around any longer and is willing to do whatever it takes to get him and Billy to safety. So again, while I don’t think Emmett set out to murder Duchess, I also believe he didn’t care what happened to him—he just didn’t want to deal with his toxic behavior any longer.

Tell Me Your Thoughts

This is how I interpreted The Lincoln Highway ending. Agree, disagree and/or have other ideas completely? Be sure to tell me your thoughts below!


Wednesday 8th of May 2024

As I recall, the 3 arrive at evening and find their dead friend. Thus NONE knew about the 'STRONG afternoon wind' the author explains as Duchess awakens in the boat! I think Emmett thot Duchess, who couldn't swim, with the position of the leaking boat would chose his life NOT the money, but be taught a huge lesson... Remember Emmett was the idol of his very bright little brother so his little brother could see this as a ' life lesson' of not just murdering a person since Duchess would have the power to make a choice... with the money at the other end of the unstable boat. However, fate took over the ending with the strong wind the money blew away and hard as he tried, Duchess could not make it back to shore loosing both....


Monday 1st of January 2024

I just finished this book and felt the urge to look up a discussion about the ending because I just couldn’t let the thoughts keep swirling around in my head! This group has brought up some very thought-provoking points. While I do agree that Duchess was ultimately the villain, a part of me feels very sorry for him. His father (the ultimate ultimate villain) failed to provide him with the basic education to ensure his success in this world, namely reading and swimming. As an illiterate, I’m sure that behind the charm and violence was a deep seated fear of how he would make it in the world. He had no family and no traditional education. As I think about it, though, I suppose he could have applied himself to become a great chef or something. It just goes to show how deep and rich Towles created these characters! I’ll have to read A Gentleman in Moscow.


Monday 1st of January 2024

I thought duchess brought in Fitzwilly to play Billy's famous I guess I was rooting for dutchess to be a better perso

Rita Lacerda

Wednesday 15th of November 2023

I had to find people to discuss this ending, so glad I came across this site! My oh my, what a twist! It's like it turned into a whole new book. I was already loving it and with an hour to go on my audiobook, I was bracing myself for a happy ending, or at least something more about the boys' mum or Duchess' dad. And then the shock of where it went. I was listening while driving and my eyes teared up at Whooly's death. I was very conflicted about Duchess' as well. It felt unavoidable given his character, but completely avoidable if he had Emmett's. Emmett would've been sensible and saved his life and whatever money was left, which is why I choose to believe he didn't set out to kill Duchess. He might have even made it to shore, repaired the boat and set out again to collect the drifitng notes or something. Emmett also didn't know about the breeze so he could have genuinely assumed the lake would remain still for as long as it took Duchess to paddle back.

I agree with others who have mentioned Billy is autistic. It was very obvious. But I believe Whooly was too, which explains why they got on so well. Generous to a fault, the way he saw the world, his special interest in Abraham Lincoln, his difference from his family, his unusual collections, the literal interpretations, the naïveté and sense of wonder, all screamed autism to me. I don't think he was contemplating suicide the whole time. For me, it was the conversation with his brother-in-law that was the tipping point. The whole thing about him having to get a job and start becoming a man, it was too much to face. He realised he would never be free of the world's and his family's expectations of him. He drops his hope to see the Statue of Liberty, which struck me as odd at the time, but I hadn't realised he made the plan to end his life, I was still thinking he would start over in California with the others. But a family with that reach and influence, they wouldn't let him go and he probably assumed that would make his friends a target as well. Poor Sarah, to face the death of her beloved brother while pregnant as well. I do agree with Emmett, she would not forgive herself. Regardless of the brown bottle not being linked to the scene.

I feel this book is going to leave me reeling for a long time. I'm off to find a Gentleman in Moscow next. Apparently that's the thing to do!


Friday 10th of November 2023

I don't think Emmett deliberately killed Duchess. Although he knew he couldn't swim, Duchess could have made it safely to shore if he used his wits. The breeze could have taken him safely to another shore. As for the money flying around from the breeze, a well thrown stone or shirt could have safely secured the cash until he could recover it when he reached shallow water. Another point is once Duchess was capsized, he could have held on to the overturned boat and kicked his way to shore, maybe collecting money along the way....