Sixteen years ago he was a player with the club when they fell agonisingly short of the Leinster title against Thomas Davis thanks to the Dublin side’s goalkeeper’s save in a last minute one-on-one.
The winning margin in that final? Two points.
Flanagan’s next tilt came in 2007 while at the helm of Westmeath’s Tyrrellspass but, once again, it was a Dublin outfit that kept him at arm’s length. That time St Vincent’s proved too strong in the decider.
Now here he is again, back with Clara and just 120 minutes away from that elusive title after a campaign in which they have consistently upset more fancied opposition both in Offaly and in Leinster.
“To be honest,” he said, “Clara had only reached the county quarter-final last year and a lot of people would have felt that they didn’t have much prospect of doing all that well in Offaly this season.
“The players worked extremely hard this year though. They have been going for 11 months now and are still up for it. Even the training sessions we have had the last few weeks have been great fun.”
Prior to this year, their last county title was secured in 2003 and it was their current coach who led them to the promised land back then too.
Their credentials were still being viewed with some suspicion this year until they saw off a highly-rated Rhode side. After defeats of Kildare’s St Laurence’s and Carlow’s Rathvilly, Clara’s progress was temporarily halted last weekend by the weather conditions which caused their semi-final against Portlaoise to be abandoned shortly after half-time.
Clara were a point to the good at that point and against an opponent which carried far more in the way of expectations. The sides will meet in O’Moore Park again this Saturday.
Though not strictly a replay, the worry for the Offaly champions is that the rescheduled fixture will follow the long-established trend whereby underdogs rarely do well when handed a second bite of the cherry.
“Obviously, the two teams will know a lot more about each other at this stage but the weather was so poor the last day, it didn’t really allow for any real analysis,” said Flanagan who has just the one injury concern ahead of the second meeting but fully expects centre-back Matthew Mitchell to recover from a knee injury.
Should they come through on Saturday, Flanagan would be preparing for a final against a Garrycastle side who limited Ballyboden St Enda’s to just six points in the other semi-final.
“I knew ‘Boden were missing a few players and Garrycastle had been training hard all this year. I thought Boden would score more but all credit to Garrycastle for their workrate.”