Mike Pence was a young lawyer on the rise, challenging a longtime Democratic congressman in a Republican-leaning Indiana district.
And then, scandal.
Campaign finance records from the 1990 effort showed that Pence, then 31, had been using political donations to pay the mortgage on his house, his personal credit card bill, groceries, golf tournament fees and car payments for his wife.
The spending had not been illegal at the time. But it stunned voters - and undermined Pence's strategy to portray the incumbent, Rep. Philip R. Sharp, as tainted by donations from special-interest political action committees.
"It was a brazen act of hypocrisy," said Billy Linville, who was Sharp's campaign manager. "It was a bombshell, for sure. . . . Without question, he may well have won the election if it had not been for that."
Pence's early stumble proved to be a defining moment, prompting a period of public remorse that helped create the wholesome image many Republicans now say makes him an ideal running mate to counterbalance the bombastic Donald Trump.
In the months after that 1990 defeat, Pence waged a statewide apology tour and disavowed negative campaigning. He told a local reporter that using campaign funds for personal expenses had been "an exercise in naivete."
Pence's 1990 race also led to key changes in campaign finance policies. Experts say that subsequent rules passed by the Federal Election Commission barring the use of campaign funds for personal needs were the direct result of ethics concerns raised by Pence's actions.
Jason Miller, a Trump campaign spokesman, said that Pence had done nothing wrong in the 26-year-old episode and that the FEC had determined that he was "100 percent compliant with the law at that time."
Pence first challenged Sharp in 1988, losing to the then-seven-term incumbent by more than six percentage points. Pence's line of attack was narrow, mostly focused on the support Sharp received from PAC money.
But that campaign provided early hints that Pence was willing to go for the jugular. One Pence mailer depicted images of a razor blade, white powder and rolled-up cash, and declared: "There's something Phil Sharp isn't telling you about his record on drugs." The brochure left readers hanging until a subsequent page: "It's weak," the ad read, using letters formed in powder.
The Washington Post obtained a copy of the brochure from Sharp's archived papers at Ball State University in Muncie, Indiana.
Two years later, Pence tried again, promising to focus on issues Indiana voters cared about and accusing his Democratic opponent of favoring big government. Pence wanted to win so badly that, according to a local newspaper report at the time, he kept a sign in his office that read "congressman in training."
When news of Pence's campaign spending broke, his opponent made the most of it. Linville, Sharp's campaign manager, held a news conference, waved Pence's campaign finance reports in the air and declared, "If you're giving money to Mike Pence, you're paying his mortgage."
Pence was unapologetic at the time, telling reporters that he had taken a 30 percent pay cut to run for office and needed the money. "I'm not embarrassed that I need to make a living," he said.
Miller, the Trump campaign spokesman, pointed to the FEC's proceedings to underscore that Pence had done nothing wrong.
"The nonpartisan Office of General Counsel at the FEC reviewed them, and the complaints were dismissed," Miller said.
Pence, who had incorporated his deep Christian faith into his campaign, also had to deal with the repercussions of his negative efforts, which had hurt his public image.
He offered advice for how would-be candidates could avoid the financial pinch that led him to tap campaign funds for personal expenses: "Don't quit your day job."