Heck, earlier this week his main concern was getting a top-25 finish so he could play in the next event.
But after a whirlwind four days, Flanagan got up-and-down from the greenside bunker on the 18th - on the third playoff hole - to win the BMW Charity Pro-Am over Cameron Percy. Flanagan and Percy both completed 72 holes at 15-under par.
"I'm very glad that bunker shot went to a foot," Flanagan said. "So that I wouldn't have to think too much about the next one."
Percy struggled at the 18th in regulation to open the door for Flanagan. Playing in the group ahead, Percy pushed his approach on the long par-4 into the greenside bunker and missed a 10-foot downhill par attempt. Ten minutes later, Flanagan sunk a 10-foot putt of his own - this one for birdie - to force the playoff.
Flanagan will admit that he got lucky on his approach, as his shot from 206 yards out flew the green - but bounced off the grandstand and back within 10 feet.
"I got super, super lucky," Flanagan said. "It took a long time to come back onto the green. I didn't realize it was 10 feet, but I'll take it."
The win does a lot for Flanagan's career. Playing on conditional status, this was only his second event of the year. Now he has full Nationwide Tour status for this year and next, and he no longer has to worry about eligibility on a week-to-week basis.
Not only is he surprised to be holding a trophy, he is rather surprised that he is still playing competitively at all.
"It's been so long since I've been playing golf tournaments," Flanagan said. "Three or four years ago when I started struggling, I didn't know if I'd be playing tournament golf at all. I'm pretty happy to win."
That's because in 2007, after winning three Nationwide events to earn a mid-season promotion to the PGA Tour, Flanagan's game began to fade. After striving for years toward gaining eligibility on the PGA Tour, he couldn't get comfortable when he finally got to the big stage.
He found that the Tour was more professional than social. Golf was the sole focus, and Flanagan found it difficult to push forward whenever his game stalled.
"I hadn't grown into it yet," Flanagan said. "Week to week, I felt like I was battling the whole time. It's hard to get motivated when you're playing terrible, and I didn't feel like I was part of the Tour."
The culture change led Flanagan into a downward spiral with his golf game, where he went five years without a win. That is, until things came together this week in Greenville. After years of struggle, it looks like Flanagan is finally finding his way back.
It's a good thing, too, because he doesn't really know what he would do otherwise.
"I don't really know how to do anything else," Flanagan said.
For at least the next year and a half, he won't need to.
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Percy looked to be in control of the tournament down the stretch, but a few miscues did him in. After a long backup on the 16th tee box, he managed to reach the par-5 in two strokes. However, he left his eagle putt 8 feet short and missed the birdie bid, failing to take advantage of the short par-5.
To Percy's credit, he responded with a 18-footer for birdie on the par-3 17th, but the untimely bogey on 18 allowed Flanagan to take advantage.
Flanagan did take advantage of the back-to-back short par 5's, 15 and 16, with birdies on both. Flanagan had seven birdies in total on the day, and he needed them all to force the playoff.
Percy had a chance to win on the first playoff hole with a 10-footer for par, but was unable to will it in. Percy remains winless on the Nationwide Tour, while Flanagan notches his fourth career win.
Still, Percy will take positives from the week. After leading by two strokes going into Saturday, he went 6-over par over his first 11 holes and found himself back in the pack.
But Percy knew there was still a long way to go, and he was able to fight his way back into contention over the last 25 holes of the tournament. He may not have closed the deal this time, but he is confident at his prospects moving forward.
"I still felt like I could shoot anything here," Percy said. "I saw the leaders hadn't gotten too far ahead. I'm looking forward to playing Raleigh next week, and I'll try to get a win there."
Darron Stiles looked to be in good shape to contend for the title, at 15-under with four holes to play. But Stiles failed to take advantage of the short par-5's, and he bogeyed 18 to share third place with Robert Streb.
Third-round co-leaders Brad Fritsch and Steve LeBrun failed to make noise down the stretch. Fritsch shot a 70 that left him tied for 5th, and LeBrun struggled to 74 and a T22.
The Tour returns to action in two weeks, for The Rex Hospital Open in Raleigh.
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