‘Winning a Gold Cup is like sex – you always remember your first time!’ – Michael O’Leary on Cheltenham’s greatest prize

RYANAIR millionaire Michael O’Leary says ‘winning a Gold Cup is like sex – you always remember your first time!’

I’ve never thought of it like that.

Our man Chappers caught up with top owner Michael O’Leary

The Ryanair boss has been a successful owner for a number of yearsSportsfile

But that’s probably because I’ll never own the winner of a Cheltenham Gold Cup.

At least I have the memory of one of the two, although not a particularly great one.

O’Leary has experienced both. And the Gold Cup not once, but twice. He is certainly no Festival virgin, that’s for sure.

And he has a third chance of landing the ultimate prize with Conflated running in his Gigginstown House Stud colours in the big one.


There’s no doubt the entrepreneur is a love or hate character, something some of us know all about, but I find his enthusiasm infectious.

He’s like a buzzing bee when I get to chat to him at his plush Ryanair offices in Dublin.

The 61-year-old is polite. Great fun. He gets banter and buys lunch!

But, boy, he’s agitated.

Just like the jet engines on his planes, you can almost feel his mind constantly churning over.

Always in overdrive. You wonder if he ever stands still.

He’s in the office working most days, incidentally, and runs Ryanair more like a family business than anything else.

So is winning the Gold Cup with Conflated the ultimate for a man worth in the region of £900million. As he said to me, no one knows the exact figure, probably not even him.

“It’s the most important race for me by a distance,” O’Leary explains.

“It’s the one everybody wants to win at Cheltenham. I’d take it over the Champion Hurdle, Grand National or Derby — and every other race.”

It seems O’Leary was bitten by the racing bug in his early days.

He tells me: “As a kid the first race I watched was the Grand National — I remember the TV coverage starting at 11am and we would watch all day.

“But I think you are naturally drawn to the Gold Cup. It’s the pinnacle and the best chasers and best horses usually win it.”

I cheekily suggest the Gold Cup is a better race than the Ryanair.

O’Leary pauses, winces, and then says: “I think it’s a close run thing but history would tell you it’s marginally better than the Ryanair Chase.

“But the Ryanair Chase is coming up the inside which is why we have extended our sponsorship for another four or five years which takes us up to about 22 years of sponsorship.”

O’Leary has won the Gold Cup twice — with War of Attrition in 2006 and Don Cossack ten years later.

“War of Attrition was trained by Mouse Morris and ridden by Conor O’Dwyer. He was really a two or two and a half mile horse, but had injury problems as a novice chaser.

SportsfileO’Leary has had plenty of winners at the Festival[/caption]

Getty Images – GettyHis horse Don Cossack won the Cheltenham Gold Cup in 2017[/caption]

“He was a great chaser but after he won it he had a tendon injury and was never quite the same again.

“Like sex, you always remember your first Gold Cup.

“On my death bed I will remember the birth of my four children, the marriage to my wife and War of Attrition winning the Gold Cup.”

Don Cossack was a monster as a Bumper animal, but then lost his way over hurdles. O’Leary says: “He was a super chaser, and it took us a while to work him out. AP rode him in the Melling Chase and he banged him out and won by a distance.

“Bryan Cooper gave him an awful ride in the King George, then a great one in the Gold Cup. That was very memorable as we’d had a bad Festival up until then that year.”

Now O’Leary relies on Conflated, who fell in the Ryanair last year but comes into the main event on the back of a Grade 1 success in the Savills Chase at Leopardstown.

So what chance does he think he’s got? Ever the straight-talker, of his leading contender O’Leary says: “I think really we have no chance.

“If Galopin Des Champs stands up he will win. If something goes wrong with him it’s a pretty open race and I think Conflated has the quality to win an average Gold Cup.

“He’s not a superstar. “We ran him in the Ryanair last year and he was probably going a shade too fast. He will be suited by the three miles and two furlongs and he’s won two Grade 1s round Leopardstown.

“He deserves to be there, I just don’t think he has the quality to beat an in form Galopin Des Champs.”


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Galopin Des Champs is trained by Willie Mullins, a man who used to train horses for O’Leary, then didn’t, but now does again.

So what’s the story? “It was like a divorce,” O’Leary said. “Willie put up the training fees and we couldn’t agree on them so we took the horses away.

“It’s a mistake for anyone to take horses away from Willie, but a lot of those horses went to very good homes.

“That said, Willie has a great buying and training operation. He’s not the multiple champion in Ireland for no good reason.”

O’Leary won the Gold Cup in 2006 and 2016, but is downsizing now.

He said: “I was buying north of 50 or 60 horses a year and now I’m buying five to ten.

“I just don’t have the time for it with four teenage children. I’ll have two or three runners at Cheltenham in future rather than 20 or 30.

“There are different things in my life now. My time needs to be devoted to my children now. When they grow up and fly the nest things may be different.”

O’Leary is still mad keen on racing though and would love to see Conflated fly in.

Not everyone takes to him. I do.


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