TERRE HAUTE, Ind. — Nobody is tired of winning here.

Not at the Crossroads Cafe, where regulars pick at politics over breakfast. Not at the Rotary Club, where the meeting dutifully opens with the invocation, Pledge of Allegiance and four-way test for ethical behavior. Not at the Indiana Theater, a grand venue where thousands crammed in on May 1, 2016, to see Donald J. Trump, the candidate who vowed to win so much that Americans would become weary of it.

Here in Vigo County, that disappointment carries extra weight — and perhaps a warning sign for the president. For more than a century, its voters have been almost unerring in choosing the winning presidential candidate, and last year they broke convincingly for Mr. Trump.

But now, the president’s grip on voters here seems shaky.

“Winning? I don’t get a sense that we are winning,” said Bart Colwell, the president of the Terre Haute Savings Bank, who described himself as a Republican but declined to say whom he voted for in November. “I think his tone is pretty negative. His tone would not be a tone that most people in leadership would use.”