Now, with the Buckeyes headed to the NCAA semifinals in St. Petersburg, Fla., O'Brien is a mystified as anyone.
"I personally just wanted to win more than we lost. I know it sounds a little ridiculous right now but I thought that was real," he said. "I just thought that after five straight losing seasons that a winning record would have been nice."
In O'Brien's first season at Ohio State, the Buckeyes went 8-22, losing 17 straight games and tying the school record for losses.
Even the most ardent fan would have felt foolish to ask for a winning season this year.
"I thought that would have gotten us to the NIT and would have shown some pretty good progress," O'Brien said. "Obviously, we have far exceeded that."
Yes, they have. The record is downright startling: 27-8, with Connecticut (32-2) up next on Saturday night.
The latest victory came in the South Regional title game, a 77-74 win over St. John's 77-74.
This is the Buckeyes' first trip to the Final Four in 31 years. The last time they went, O'Brien was a scrawny freshman point guard at Boston College.
The captain of the last Ohio State team to make it to the Final Four gives a lot of the credit to O'Brien for the remarkable turnaround.
"He's the catalyst," said Bill Hosket, a Columbus businessman and Big Ten basketball commentator. "He's getting the most out of the kids, but more than that he's doing a terrific job of hiding their weaknesses. That's something he's done well for two years.
"There's no question of which team had the best coaching in the last 80 minutes of basketball I saw in Knoxville. It's phenomenal what the guy has done."
Ohio State's leading scorer, Michael Redd, said there are several reasons why the Buckeyes have survived this long and all are attributes nurtured by O'Brien.
"Teamwork. Playing hard. Every possession we played with a lot heart," he said. "That was the key for us. It really was."
Before the season, point guard Scoonie Penn brashly predicted the Buckeyes would make it to the NCAA tournament.
"I'm looking at him like, you know, he's nuts," O'Brien said.
Penn insists the Buckeyes are deserving of the trip to St. Petersburg.
"It's something we work real hard for," he said. "I don't think anyone thought we could do it, but here we are."
When he took over the Buckeyes two years ago, O'Brien inherited several malcontents and borderline players. All but two transferred or quit: seniors Neshaun Coleman and Jason Singleton.
This season, O'Brien points to the character of his players and the contributions from the entire roster.
"Just when you don't know if they can keep iving there's always more," he said. "They always come back."
O'Brien has been a head coach for 17 years at Ohio State, Boston College and St. Bonaventure. He was an assistant for five years before that at, of all places, UConn.
The moment is not lost on him. He hugged his daughters and then danced with his players after the victory over St. John's.
"Guys coach forever and ever and never get a chance to get to the Final Four," he said. "People go through their careers, players play three or four years, and never get this opportunity.
"We just have to be thankful that we get this opportunity. It's special."
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