Woolly Wolcott Character Analysis in The Lincoln Highway

Woolly Wolcott is one of Emmett’s friends from Salina. He comes from a wealthy family, but he has been disinherited since his relatives consider him “temperamentally unfit” to receive his trust fund. Woolly struggles to think through the consequences of his actions, but he cares deeply about the people around him and wants to help his loved ones. After he escapes from Salina with Duchess, Woolly agrees to split his trust fund equally with Duchess, Emmett, and Billy if the boys successfully steal the money. Woolly has a troubled relationship with his family, but he is close to his sister Sarah, and he treasures his memories of his childhood at the family’s house in the Adirondacks. When Duchess brings Woolly back to the Adirondacks house, Woolly feels at peace and decides to take his own life. His decision is, at least in part, shaped by a desire to stop being a burden on his loved ones. In one final act of love, he leaves a last will and testament that splits his trust fund evenly among his friends.

Woolly Wolcott Quotes in The Lincoln Highway

The The Lincoln Highway quotes below are all either spoken by Woolly Wolcott or refer to Woolly Wolcott. For each quote, you can also see the other characters and themes related to it (each theme is indicated by its own dot and icon, like this one:

[…] it suddenly occurred to Woolly that maybe, just maybe, St. George’s and St. Mark’s and St. Paul’s organized every day to be an every-day day not because it made things easier to manage, but because it was the best possible means to prepare the fine young men in their care to catch the 6:42 so that they would always be on time for their meetings at 8:00.

Related Characters: Woolly Wolcott, Sarah Whitney, Dennis Whitney

Page Number and Citation: 100

Explanation and Analysis:

––I’ll start in front of the cabinet at FAO Schwarz, he said to himself with a smile. And my sister will come […]. And after Duchess meets me at the statue of Abraham Lincoln, he and I will attend the circus, where Billy and Emmett will suddenly reappear. Then we’ll go over the Brooklyn Bridge and up the Empire State Building, where we’ll meet Professor Abernathe. Then it’s off to the grassy train tracks where, sitting by the fire, we’ll hear the story of the two Ulysses and the ancient seer who explained how they could find their ways home again––how they could find their ways home, after ten long years.

But one mustn’t rush, thought Woolly […]. For a one-of-kind kind of day deserves to be relived at the slowest possible pace, with every moment, every twist, every turn of events remembered to the tiniest detail.

Related Characters: Woolly Wolcott (speaker), Emmett Watson, Billy Watson, Duchess Hewett, Ulysses, Sarah Whitney, Professor Abacus Abernathe

Page Number and Citation: 501

Explanation and Analysis:

––You should have been there when your brother talked about the house he wants to build in California. I’ve never seen Woolly so excited. He could just picture the two of you living there together. If we go to the cops now, I’m telling you, within the hour this place is going to be crawling with people, and we’ll never get to finish what Woolly started.

Related Characters: Duchess Hewett (speaker), Woolly Wolcott, Emmett Watson, Billy Watson

Page Number and Citation: 540

Explanation and Analysis:

Sitting together on a nearby bench were Woolly and Billy, smiling at the floor plan of the house in California. And there was Sally leaning over a pram to tuck in the blanket of the child in her care. And there by the flower cart was Sister Sarah looking wistful and forlorn. And right there, not more than fifty feet away, standing by the door of his bright yellow car, was Emmett, looking honorable and upright.

[…] I could hear the distant chiming of a clock. Only it wasn’t a clock, and it wasn’t distant. It was the gold watch that had been tucked in the pocket of my vest […].

Related Characters: Duchess Hewett (speaker), Woolly Wolcott, Billy Watson, Sarah Whitney, Sally Ransom, Emmett Watson, Harrison Hewett

Page Number and Citation: 576

Explanation and Analysis:

Woolly Wolcott Character Timeline in The Lincoln Highway

The timeline below shows where the character Woolly Wolcott appears in The Lincoln Highway. The colored dots and icons indicate which themes are associated with that appearance.

...chapter switches to 1st person as Duchess gleefully compares Emmett’s surprise at seeing him and Woolly to a crowd witnessing a stage magician’s trick. Duchess explains to Emmett that he and... (full context)

Once they are alone, Emmett asks Duchess what he and Woolly are doing in Nebraska. Duchess explains that he has no intention of returning to Salina,... (full context)

...enjoys Sally’s “country cooking” and the Watsons’ quaint lifestyle. As they dine on the casserole, Woolly asks Duchess about “the escapade,” and Duchess tells Emmett that Woolly’s family has deemed him... (full context)

...walks to the Ransoms’ house to ask them to jumpstart his car, leaving Duchess and Woolly with Billy. Duchess talks to Billy about The Three Musketeers, pointing out that the story... (full context)

...so Duchess grew up running with his father from bill collectors. Duchess joins Billy and Woolly in Billy’s bedroom, and Duchess explains to Billy that his nickname comes from his birthplace,... (full context)

While Duchess and Emmett are in town, Woolly is alone in the house with Billy, watching the boy read a book that contains... (full context)

Woolly flashes back to the first time he repeated his junior year of high school. He... (full context)

Emmett plots out a route for San Francisco, intending to drop Woolly and Duchess off in Omaha along the way, and he and the others depart early... (full context)

...find Duchess in the building, and when he emerges, Billy informs him that Duchess and Woolly have “borrowed” the Studebaker for a trip to New York. Emmett calls Sally, who agrees... (full context)

...the Lincoln Highway, appreciating the contented purposelessness he sees in the towns that he and Woolly pass. Woolly adjusts the car radio, turning through channels to listen to commercials. After listening... (full context)

The Studebaker starts to slow, and Duchess doesn’t know why until Woolly points out that the car is low on gas. Duchess parks the car and heads... (full context)

...avoid upsetting Billy, a “stickler” for all rules. Billy compares the plan to Duchess and Woolly’s escape in Warden Williams’s car, which Duchess told him about. Emmett tries to warn Billy... (full context)

Duchess and Woolly spend the night in a Howard Johnson’s outside of Chicago. Woolly is well-travelled, but he... (full context)

Duchess and Woolly eat an early breakfast at Howard Johnson’s, though Woolly ignores his food in favor of... (full context)

Woolly drives contentedly, unaware that he is frustrating other drivers. He likes the simplicity of the... (full context)

As Woolly walks back to the Studebaker, he crosses paths with a man in a large hat... (full context)

Duchess finds Woolly by the Studebaker with a police officer, who intends to arrest him. Duchess pays the... (full context)

Woolly dislikes Manhattan and wants to go right to Sarah’s house, but he accepts that Duchess... (full context)

Woolly and Duchess arrive at Woolly’s family home, where Sarah lives with her husband Dennis, but... (full context)

Later, when Sarah returns, she apologizes for clearing out Woolly’s room to use as a nursery for the baby she’ll soon have. Woolly appreciates that... (full context)

Woolly stands in FAO Schwartz, a large New York toy store, happily admiring the dollhouse furniture.... (full context)

While Woolly and Sarah are in the city, Duchess has the run of Sarah’s house, listening to... (full context)

...afraid that Duchess will hurt him. Emmett and Billy watch the circus until Billy spots Woolly in the audience. Emmett brings his brother over to Woolly, who tells him that Duchess... (full context)

Duchess leaves Emmett at Ma Belle’s and drives into the city with Woolly and Billy. Woolly points out the Empire State Building and Billy requests they visit, since... (full context)

The story flashes back to provide Woolly’s perspective on the visit to the Empire State Building. His travels with his family have... (full context)

Billy leads Duchess, Woolly, and Abernathe to the railroad camp, and Woolly pauses to appreciate the wildflowers growing on... (full context)

Back at Sarah’s house, Woolly and Duchess prepare dinner while Billy grows anxious about how long Emmett has been gone.... (full context)

...time, Duchess also calculates the expenses he will pay Emmett for once the boys have Woolly’s trust fund. As the evening progresses and Emmett doesn’t arrive, Duchess calls the brothel. Ma... (full context)

...forgot to leave an address, so Ma Belle searches the Social Register for information on Woolly’s family, since they are old money in New York and Duchess mentioned he was staying... (full context)

Woolly takes Billy upstairs and shows him his collection of discarded objects, which Woolly compares to... (full context)

...with $3,000 and the summary of what he will pay Emmett after the boys steal Woolly’s money from the Adirondacks. Emmett insists he won’t go to the Adirondacks, but Duchess points... (full context)

The story flashes back to the day Sally calls an Episcopalian priest, since she knows Woolly is Episcopalian. The day is a Friday, when Emmett is supposed to call Sally to... (full context)

The morning of June 20, Duchess and Woolly sneak out of Sarah’s house and drive off in Woolly’s convertible. They drive to Woolly’s... (full context)

Woolly brings Duchess to his great-grandfather’s study, which houses the safe full of money. Duchess gestures... (full context)

Emmett wakes to find that Duchess and Woolly are gone. Woolly has left a note apologizing to Sarah and telling her not to... (full context)

Sarah explains that Woolly was sent to Salina because he saw a firetruck on the road with no firefighters... (full context)

Duchess goes to the general store, leaving Woolly to reminisce about his childhood memories in his great-grandfather’s house. He looks at a picture... (full context)

...“unfinished business” with Mr. Hewett and tells the others they need to find Duchess and Woolly. Billy shows Emmett his map of the Lincoln Highway, where Woolly marked his address in... (full context)

...into a motel for them to spend the night while he tracks down Duchess and Woolly. Sally tells Emmett she wants to go with him to California, and Emmett awkwardly tells... (full context)

Emmett drives to Woolly’s family’s Adirondack house and searches the massive property for his friends. He looks through various... (full context)

...He finds Duchess desperately hitting the safe with an ax. He accuses Duchess of letting Woolly kill himself, but when Duchess protests that he didn’t find Woolly until he was already... (full context)

The story flashes back to the previous day. After Woolly reveals that he can’t open the safe, Duchess spends hours trying to break it open.... (full context)

...Duchess rationalizes this as Emmett “acting a little crazy” in response to his grief over Woolly. He sees Billy’s arrival as an act of fate that he can take advantage of,... (full context)

...outside the house in the Adirondacks, Billy emerges. He recognizes places on the property from Woolly’s stories about the house, and notes a checklist of housekeeping duties for “closing the house.”... (full context)

...been “forsaken,” just like Ulysses, so he kicks Duchess and hides in a small alcove Woolly told him about. (full context)

...the rules for closing the house and doesn’t know that the guns are unloaded when Woolly’s family is not in residence. Emmett grabs the rifle, and Duchess protests that he would... (full context)

Billy gives Emmett Woolly’s suicide note, which asks that his inheritance be distributed evenly among Emmett, Billy, and Duchess.... (full context)

...trace that they were there and drag Duchess outside. They say a final goodbye to Woolly, then return to the Studebaker to pick up Sally. Emmett agrees to take a detour... (full context)

...finds himself on a crowded street full of people he knows standing frozen in place: Woolly, Billy, Sally, Sarah, and Emmett. Duchess bows to each one of them and wonders which... (full context)

The Lincoln Highway

Woolly Wolcott Character Analysis

Woolly Wolcott Quotes in The Lincoln Highway

9. Woolly Quotes

2. Woolly Quotes

1. Emmett Quotes

1. Duchess (2) Quotes

Woolly Wolcott Character Timeline in The Lincoln Highway