The Gordon Elliott-trained eight-year-old can be bet at 10-to-1 on both the Ryanair Chase and the Boodles Cheltenham Gold Cup, having won the Grade 1 three-mile race at Leopardstown at 18-to-1 a fortnight ago.
But concerns over Conflated's stamina for the Gold Cup's extended three-mile, two-square trip could see Yeats' son prefer the Ryanair Chase over two and a half miles on Thursday - the race sponsored by his owner - to the Blue Riband Chasing the following day.
"I would lean towards the Ryanair Chase," said O'Leary's brother and race director Eddie.
"It looked like it would stay all day at Leopardstown, but there's a big difference between three miles at Leopardstown and three and a half miles at Cheltenham.
Elliott had persuaded the horse's owners to let him run in the Irish Gold Cup that day, and spectators were not surprised to see him gallop away under Davy Russell, beating Minella Indo, Janadil, Frodon and Asterion Forlonge, the heroes of last year's Cheltenham Gold Cup.
Conflated is fifth in the betting for the Cheltenham Gold Cup on March 18, with odds of 10 to 1, behind A Plus Tard, Galvin, Minella Indo and Protektorat.
For the Ryanair race, for which Allaho is the clear favourite, he is also at 10 to 1 and is available at the best price (Even Money).
O'Leary recently pulled two-time Grand National winner Tiger Roll from the March event after judging the handicap weight levied as "absurd". Tiger Roll was amongst the favourites to win and was on course to make history with a third win if it were to happen. No stranger to big decisions, this may just be another in less than a month for the Irish horse owner and CEO of Ryanair.
O'Leary has three Grand Nationals and one Cheltenham Gold Cup trophies to his name, which means he knows what it takes to win.