Danforth Keeton’s first winning bet at Lewiston Raceway is the decisive beginning of his gambling obsession and, through the chain of losses and concealment it sets in motion, of his financial and civic collapse. The night gives him an intoxicating experience of chance apparently answering desire: a five-dollar wager pays off at long odds, and a brief triumph becomes a habit he cannot control. Its later consequences expose the difference between the money he hopes to win back and the public funds he risks to hide what he has lost.

The First Bet

Keeton reaches the track with Steve Frazier after an evening at The Holly. Frazier urges him toward the betting windows, while Keeton protests that he knows nothing about racing. At the two-dollar window, Keeton pushes a five-dollar bill across and chooses number four. The bet is not the considered move of an experienced gambler; it is an impulsive entry into a world whose scale immediately captures him.

While the teller waits for Keeton to specify whether the wager is to win, place, or show, he notices clerks behind the counter counting and banding stacks of cash—more money than he has ever seen together. The spectacle helps turn a small bet into something larger in his imagination. When the race is announced, Keeton feels a sudden surge of electricity and follows the horses to the rail, where he can watch the finish from less than twenty yards away.

The horse he backed, Absolutely, initially runs sixth. Keeton nevertheless fixes on her, sending what he imagines as telepathic strength toward the horse. As the leaders tire near the finish, Absolutely gains ground, passes Broken Field and How Do?, and wins. The reversal converts his wager from a likely loss into a startling success: Frazier tells him that Absolutely was a 30-to-1 shot. Before leaving the track that night, Keeton has made just over three hundred dollars.

A Windfall Becomes a Compulsion

The win does not teach Keeton caution. It teaches him to return. Having celebrated his first success, he later bypasses the two- and five-dollar windows and bets at the ten-dollar window. He loses $160, a sum that unsettles him but remains within what he can afford. He lies to Myrtle about the amount, telling her the loss was forty dollars. The concealment begins early: even before the losses become catastrophic, gambling creates a private account of events that differs from the one he gives his wife.

Keeton returns the following week intending to recover the money and leave even. He nearly succeeds, but the near recovery only prolongs the cycle; the next week he loses $210. The repeated effort to undo a loss turns gambling into an open-ended pursuit. Rather than stopping at a defined limit, he treats each setback as a temporary imbalance that another wager might correct.

The losses then reach beyond Keeton’s personal finances. When the shortfall creates a hole in the checking account that Myrtle would notice, he takes $100 from the town’s petty-cash fund to cover it. He regards the amount as trivial, but its source changes the nature of the problem: money entrusted to him in public office is now being used to conceal private gambling losses. The first winning bet has thus become part of a chain in which each attempted repair creates a more serious breach.

From Concealment to Embezzlement

Keeton is a certified public accountant, and he uses his financial knowledge to keep the scheme going. By autumn 1990, the concealment is beginning to come apart. He continues hoping to recoup his losses at the track and has found a bookie, allowing him to place larger bets than the track will accept. The larger channel for wagering does not improve his luck; it enlarges the scale of the danger while leaving the underlying behavior unchanged.

The book’s account of his municipal records makes the fraud concrete. Keeton keeps correspondence from the Bureau of Taxation in a locked bottom drawer, separating it from his replies. Although the letters bear the initials of his secretary, Shirley Laurence, she has typed none of his responses. The records that might look like routine administrative correspondence are therefore part of Keeton’s private effort to manage exposure, not evidence of ordinary office procedure.

When the state tells the selectmen that it wants to audit all the town books, the threat extends across tax records, revenue-sharing accounts, town expenses, road maintenance, law-enforcement budgets, Parks Department spending, and even the state-funded experimental tree farm. Keeton’s private gambling losses have become a risk to the town’s accounts as a whole. As his fear turns toward persecution, the word “EMBEZZLEMENT” appears on one of the warning slips that confront him. The accusation is frightening to him not because it is wholly detached from reality, but because it names the underlying crime he has been trying to keep hidden.

The Meaning of the Turning Point

The first win matters because it supplies Keeton with a compelling origin story for his repeated return: the track once gave him an extraordinary payoff, so he keeps acting as though the next bet might restore what has been lost. The actual result is the reverse. The initial gain gives way to concealed losses, a withdrawal from petty cash, increasingly large bets through a bookie, and a looming examination of the town’s financial records.

The event also establishes the difference between Keeton’s private sense of chance and the public consequences of his choices. The race appears to reward his fixation, but the later financial records make the costs legible: funds have been diverted, official correspondence kept under lock, and a full audit is approaching. His obsession and his persecution fears shape how he experiences the crisis, yet the financial breach is not merely imagined. The first winning bet is therefore both a moment of apparent triumph and the beginning of a collapse that gambling cannot reverse.