O'Regan in uncharted territory but loving the change of pace as he heads to the Festival looking to rekindle some old fires
When the name Jeu De Roseau is mentioned, you can see the twinkle in Denis O'Regan's eye.
O'Regan arrived at a humdrum Monday evening meeting at Towcester in May of 2010 for one solitary ride as normal but he quickly knew something was up when bookmakers were staring at him quizzically as he made his way to the weighing room.
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A cryptic message earlier in the day from his agent Sam Stronge - 'Is there something you haven't told me? Do you know something I don't?' - was quickly confirmed as Jeu De Roseau had plummeted from a 25/1 no-hoper to the hottest of 6/4 favourites.
Riding for his "great friend" Chris 'Rambo' Grant, O'Regan hadn't made the connection but Jeu De Roseau was previously owned by renowned gambler Barney Curley and was the final piece of an extraordinary sting which could cost the betting industry millions.
With the third leg of Curley's audacious four-timer going down, the pressure was on O'Regan to deliver the goods in the Niftylift Handicap Hurdle but the six-year-old had beaten just four horses home in his previous five runs.
Struggling to pick up in fourth before two out, it looked like this ship would sink only for Youghal, Co Cork native O'Regan to carry him home by a length showing all the aggression of someone battling for a Cheltenham Festival winner.
Dubbed a "fine ride" by the Racing Post, the scale of what O'Regan had achieved would only become apparent when word of the near €5 million coup was headline news all around the world in the hours that followed.
Some nine years later, it still brings a smile to his face.
"It had gone quiet. I was after losing the Howard Johnson job and Barney Curley took a liking to me. It was Towcester on a Monday night. Did you know, he hadn't an ounce up his sleeve," O'Regan recalls.
"I lifted him out of it. He beat a horse of Kim Bailey's (Ruby Crown). Went off 6/4, he was 25/1 in the morning or something. How much did they make? It was millions. I had no idea. You're better off not knowing."
That's just one of many facets to a colourful career with considerable success enjoyed as first jockey to Johnson in the north of England aboard the likes of Inglis Drever - which he partnered to his third Stayers' Hurdle crown in 2008 - and Tidal Bay before switching south as more winners followed.
O'Regan was later signed up by John Ferguson, who ran Sheikh Mohammed's jumping operation, before returning home as retained rider to Barry Connell in 2016 with the pair enjoying a memorable Cheltenham Festival success two years ago with the Alan Fleming-trained Tully East.
That association came to an end last July and he's been freelancing since - most recently guiding Liam Cusack's Snugsborough Hall and Snugsborough Benny to victory - while basing himself with Gordon Elliott.
With Jack Kennedy, Davy Russell and Keith Donoghue ahead of him in the pecking order at Cullentra, it's not a position he envisaged being at the age 36, nor did he think that the first two days of this year's Festival would pass without a ride.
The veteran is going with the flow, however, and looks a man at ease with the world despite finding himself in uncharted territory heading into the biggest two days in jump racing's calendar.
"I couldn't have predicted it, no. I'd like to have ridden more winners, been in with a shout of champion jockey at some stage, but you need to be in the right yard for that, and have the right backing," he says.
"I rode for Gordon 10 years ago, rode Silver Birch to finish second in the Cross-Country. I don't come here with the view to taking over the world. I'm settled, I've a wife and child. I'm a lot happier.
"I love coming in, being part of the team again, a good team, a winning team. If something comes my way, great. The biggest problem I had was getting on a really good horse. It either wasn't fit, or not right, and he couldn't maintain a run.
"If you're in a huge yard, you get on a good horse, and you stay on him, and a good trainer can keep producing the goods with good horses.
"There is a lot of talented riders here so I wouldn't like to think I'd be overtaking any of them."
O'Regan sees himself as an advisor to aspiring jockeys in Elliott's yard and will always aid those seeking his counsel.
"I'm open to helping young lads getting through. It's hard. I've been in every position possible myself, so I'm here to help," he adds.
Describing Elliott as "one of the best trainers of all time", O'Regan heads to the Cotswolds hoping to pick up a few spare rides later in the week for the Meath trainer and to add to his four Cheltenham Festival winners.
The same fire burns inside him - this week more than ever - and he'd like nothing more than to make another mark on jump racing's grandest stage.