Tim Sypher told jurors on Thursday that Pitino asked him to take his now ex-wife Karen Cunagin Sypher to get medical aid and counseling in August 2003. Sypher ended her pregnancy with an abortion in Cincinnati and pocketed the bulk of the money given by Pitino, Tim Sypher said. Tim Sypher drove her to the appointment and the trip started a romance, he said.
"We hugged," he said. "I walked out the door and she said, 'Is that it?"'
The two would marry less than a year later.
Tim Sypher is due to continue testifying on Friday.
Karen Sypher, 50, has pleaded not guilty to extortion, lying to the FBI and retaliating against a witness. Prosecutors say she demanded money, cars and a house from Pitino to keep secret their tryst in August 2003 at Porcini, an Italian restaurant in Louisville. She also has claimed Pitino raped her that night but he has not been charged.
Tim Sypher and other witnesses said he and his ex-wife went to Louisville functions with Pitino, including a holiday party at the restaurant where the coach and the ex-model had sex.
"She was very friendly with everyone," Tim Sypher said. "No problems."
By 2007, Tim Sypher said, finances were tight and the marriage was falling apart. Attorney Dana Kolter of Louisville sent Tim Sypher a letter on behalf of Karen Sypher asking for a separation. That's the first time Karen mentioned the rape allegation, he said.
"All of the sudden she started using the 'rape' word. It just came out of the blue," said Tim Sypher, who speaks with a strong Massachusetts accent.
Over the next two years, Karen Sypher was "wishy washy" about the marriage at times hugging and kissing her husband, at other times exploding when Pitino called for something work related, Tim Sypher said. All the while, the rape allegation would pop up periodically, Tim Sypher said.
When Pitino received threatening phone calls in February 2009, Tim Sypher said the coach sent him a text message asking him to bring Karen Sypher to the basketball practice facility immediately.
"I didn't know what to think," Tim Sypher said.
Tim Sypher arranged three meetings between the coach and Karen Sypher over the next two days. During those, Pitino and Tim Sypher testified, Karen Sypher said she didn't know who made the calls and started demanding money and cars.
Jurors earlier heard testimony from Lester Goetzinger of Louisville, who acknowledged making the calls in exchange for sexual favors from Sypher.
On March 6, Karen Sypher had a letter delivered to Tim Sypher, with instructions to forward it to Pitino. Tim Sypher said he gave the coach the letter the night before a game against West Virginia.
"I really didn't know what was in there. I don't know," Tim Sypher said. "She's nuts."
The letter, shown to jurors, included a list of seven items Karen Sypher demanded, with the promise that "If all is accepted, I will protect Rick Pitino's name for life."
Pitino said in March 2009, he received a letter from Kolter, accusing Pitino of rape and forcing Sypher to have an abortion and demanded a monetary settlement to prevent a lawsuit from being filed. Jurors saw the letter Wednesday
Pitino, worried that his wife and kids would find out he had a one-night stand, acknowledged Thursday that he didn't immediately tell police about demands for cars, cash and housing in order to keep the tryst secret.
He told jurors he kept quiet for nearly two months, hoping he could "contain" the damaging information.
No one else has testified to witnessing the sexual liaison after hours at an upscale Italian restaurant. The owner said he left for the night after showing Pitino and Sypher how to get out through a self-locking door. Pitino's driver said he didn't see or hear anything because he had stepped behind a partial wall to leave the couple some privacy.
When Pitino's testimony ended, he had spent about six hours on the witness stand. His attorney, Steve Pence, said Pitino would return to recruiting later in the day.
"This matter, certainly his portion, is behind him now," Pence said. "I'm very proud of coach Pitino in how he handled this."