DRAGGING himself out on the bike after dinner on these cold, dark, wet evening following a full day in the yard is a bit of a chore but the motivation is powerful for Philip Dempsey with his participation in the John Shortt Legends Day race at Punchestown looming next Thursday.

Michael Kinane, Paul Carberry, Charlie Swan, Norman Williamson, Luke Harvey, Arthur Moore and Graham Bradley are just some of the luminaries participating as they bid to raise funds for Shortt’s wife Ann Marie and daughter Alex.

Some of the lads have been swearing that they are doing nothing but the competitive juices have resurfaced by all accounts. The word is that Lorcan Wyer has returned to riding out every day and they are all pursuing good horses. Gordon Elliott’s phone is hopping and Dempsey is hoping to be at the top of the queue. Brendan Sheridan is said to have secured a spot aboard a Willie Mullins vehicle, while Conor O’Dwyer is on a promise from Aidan O’Brien.

These lads all know their former colleagues will be unforgiving. But Dempsey, whose last ride of a career that yielded more than 200 winners was 12 years ago, isn’t worrying about their barbs. Sipping on a mug of tea in the conservatory of the totally revamped, glorious family home at Kilkeaskin House with wife Genie nearby giggling at the prospect of a continuation of the banter that is de rigeur around here, the Carbury-based trainer is dreading the grief his offspring Luke and Sarah will give him if he lets the side down.

“Them two, they’ll see any weakness,” he assures you. “You couldn’t go riding long now or anything… I got a loan of a bike off a friend and I can’t wait to give it back to him. I was out in the rain the other day and I was thinking ‘Fuck this!’”

SLAGGING

He rides work every day but is leaving nothing to chance, even doing a bit of running, though he walks until he’s out of sight of the general public.

“I’d be staggering along,” he laughs.

“The two kids of course, there’s fierce slagging here. Sarah would be saying ‘That’s my Dad, the little, fat jockey behind Richard Hughes.’ And the other lad pipes up. ‘The stump.’ You couldn’t listen to them! You can’t come out looking like Billy Bunter.”

Sarah and Luke have grown up among horses and always rode out before going to school. They both competed on the pony-racing circuit and there is a photo of them riding in the same race. Outside them are Connor King and man-of-the-hour Colin Keane.

Sarah developed a reputation for winning numerous best-turned-out prizes and having served an internship in HRI last year, is intent on a career in racing once she has finished her commerce studies in UCD.

Luke is a Cheltenham Festival-winning rider of course who has long been touted as a real talent in the saddle. He suffered the common post-claim-losing lull but is coming out the other side. Doing it on his father’s horses must make it all the sweeter and the Dempsey crew are flying right now.

IN FORM

As we sit down to talk, 11 of the last 12 horses to run over the previous 14 days have finished in the first three. Grallagh is the odd one out, having fallen, but she finishes third in a subsequent race. The crop yields five winners and puts Dempsey on six for the season. His previous best is nine and with some promising young horses just getting their campaigns under way, as well as a few for JP McManus, a new mark will surely be set.

“It’s great. The horses have been flying. There’s none of them I expected to run bad but I never thought it’d be that good. Normally when you do think it, it doesn’t happen.”

Clearly, the continuing development of his facility has had a huge impact. Having established a niche for himself, largely in the ultra-competitive point-to-point trade sector, he moved to Kilkeaskin House, where his father grew up, when his uncle Luke died.

It wasn’t just the house that needed renovation. It was a cattle farm but with acreage of more than 200, even though much of it was forestry, it was a blank canvas for a man of vision. Having had 11 acres up the road, he went for it, the ever-supportive Genie backing him all the way.

Tom Furlong was invaluable, bringing all his experience to bear in design and on-site work. The development continued this year with a four-furlong straight sand gallop added to the four-furlong round one. Outside that is a mile-and-a-half grass gallop. There is a straight schooling strip of three hurdles and three fences and another one on the turn.

He admits if he had another €100,000 he would toy with the idea of putting in a wood chip gallop but is happy with what he’s got.

Now everything is done on site. The hours wasted loading and travelling on winding roads to the Curragh are gone. At HQ you are operating by someone else’s rules, you must consider the other trainers and fit into a time slot. Here there is one boss. More than that though, the horses are more relaxed.

“You can look and admire, and the place is great, I love it, we’re all very happy up here but it has to work too. You can have all the facilities. I suppose it has taken us a while to learn how to use the gallop but I think we have it fairly right now. The temptation is to overdo it. It can be tough that gallop. So maybe it’s more speed and less distance. To go the whole way around the bottom is maybe too much.”

The staff are vital too and with about 25 or so in training, they are optimistic about the season ahead.

It’s all a long way from the boy who developed a passion for horses even though his father tried to deter him, going so far as to buy him an ass that deposited him in numerous ditches but he was never deterred. He has since trained point-to-point winners for Des, who turned 88 during the week, and harbours a dream of Luke riding a winner for his grandfather on the track, which is a distinct possibility given the level of ability Derrinross has shown in two bumpers since beating subsequent maiden hurdle winner Monbeg Chit Chat in his only point-to-point appearance at Oldtown.

SUCCESSFUL

He became very successful in the plate, riding his first winner (Ragged) for Bob Jolly and going on to work for Peter McCreery, Brian Malone, Homer Scott, Mick O’Toole and John Oxx. He was just touched off in the Kim Muir Chase at Cheltenham in 1996 and prior to that, lost the then GPT Amateur at Galway on a steward’s enquiry. But there were good days aplenty.

By the time he moved to Currabeg, he was dabbling in hunters and considering becoming a huntsman. Training wasn’t on the horizon at all. Gradually it moved that way. He did some breaking and training for Tony Martin and Arthur Moore. Then he took out a licence. Hollow Star was one of the early trading successes and he sold future Ladbrokes (now Coral.ie) Hurdle winner Abbey Lane to Willie Mullins for a tidy profit.

The ill-fated Presenting Forever, owned by long-time supporter Denis Cusack, went to Howard Johnson on behalf of the Wylies for £370,000.

Then came Jacksonslady, a filly he bought for €3,500 that won a point-to-point, the Punchestown Kidney Research Fund charity race under racing journalist Niall Cronin and five official races under Rules (including the Grabel Hurdle) in his colours before JP McManus bought her ahead of the Galway Plate in 2013. She went on to finish a brilliant third to Carlingford Lough and bag some big pots for new connections subsequently. In all, she won more than €180,000 in prizemoney.

“Before her we had the odd winner but it was the point-to-points more so. I wanted to get more onto the track although without going mad for it. You needed the horse. She brought us and luckily enough we had luck which you have to have.

“She was a great start – we were delighted to have her and she took us a long way. And it was great that she did well when JP bought her. JP and Frank Berry are great, they’re great for the industry and they leave the horse with you. He has sent some others too and it means a lot to us.”

All Being Well, Ten Ten, Whatareudoingtome and Coeur Joyeux have raced in the famous colours for Dempsey this season but the pick of the bunch could be Teacher’s Pet, a young mare with a staying pedigree that has already run five races.

For the most part though, Dempsey has to buy his own stock.

“Mickey Browne (father of pinhooking legend Willie) told me one time you can be the best judge in the world but no man can walk up to any horse and say ‘This horse will win a race’. You can pick a nice athlete obviously. If a horse is falling over himself, the chances are he’s useless. But you don’t know if it’s a good one.

“I bought The New One as a foal for Denis and everyone knocked him as a three-year-old. David Minton bought him for the same price in June, sent him to Nigel Twiston-Davies and he won his bumper in November. Denis was raging for letting him go but it proved that no-one knows. All the experts looked at him. He was one that got through.”

ATTRACT ATTENTION

Derrinross, Stowaway Forever and Chesterfield King are three with nice bumper form he thinks will improve for jumps and he has a few he thinks might win between the flags and hopefully attract the attention of the big-money buyers.

Mr Diablo is another family favourite but is currently on the easy list. A four-time winner who had already suffered a serious tendon injury, the eight-year-old shattered a carpal bone in Killarney.

“He’s actually down the field but (the vet) Ger Kelly is hopeful he’ll come back after Christmas. He’s a funny horse but on his day he could be very good. He was an awful horse to break. Tom Dowling got 13 straight falls off him. And he wouldn’t just give you a fall, he’d absolutely poleaxe you. He’d explode. The squeals of him when you’d put the saddle on him.

“I was fairly good on a rough one in my day. I was watching and sick of looking at lads and said ‘Sure he only needs a bit of pulling together’, so one Saturday, he was after riding out all week, I thought he wouldn’t be too bad.

“Vlad, who was a great lad from Ukraine that worked for me said ‘Mind!’ and I said ‘Oh let him go’ and gave him a kick in the belly. Well he just exploded and my head was the first thing that hit the ground. I couldn’t get up. I couldn’t let on I was hurt. I had to drive Luke to Wexford that day and I remember sitting in the car park there still trying to get myself together! He was a brat and then he turned out a good one.”

Dempsey is pragmatic about the game though and knows that injuries are part and parcel of it. He is fully aware as well that his horses will stop running so well. He sees the changes in the fortunes experienced by the likes of former employers Oxx and Moore and knows that he could not possibly be immune. It isn’t something he is complaining about though.

“You need the big man too to buy horses. They’re doing a good bit with those rated races (for the smaller man). They had a race in Tramore for horses that had never been in the first four. That was a great idea.”

It’s very easy to whinge about racing. I don’t think it’s in a bad place at all. In every walk of life, it’s tough. You have to keep fighting. If you want to stay there, you’ll be there. I was at it for plenty long. I was always fighting.”

Injuries happen to jockeys too and Genie doesn’t watch Luke’s races live. Philip isn’t immune to worry either and was in Dundalk when his son suffered a heavy fall from the ill-fated Toberton.

“Before the horses pulled up I was beside him. He was gurgling on the ground. I thought he was dead. It was an awful fright.

“It’s great to have him; he knows the horses so well and gives good feedback. We mightn’t agree on everything but we bounce off each other well. He’d know the way I think and when it comes to the race, I’ll nearly leave it up to him. You can give all the instructions in the world and it could be gone as soon as the tape is up. So he’ll know if it’s not working he’s to do something else. And I see it, I understand that.”

He’s not one for issuing post-race bollockings he says.

“It’s done. When you’re starting off you’re thinking this and that but sure at the end of the day, they were probably no good anyway. It’s very easy to blame a lad, ‘Why didn’t you go through the gap?’ but sure the gap was probably going faster than you were. I know from riding myself. When you’re on a good horse it’s easy.”

THURSDAY

Dempsey is desperate for a good one on Thursday. Shortt had wanted to buy a plot of land and build a house for his wife and daughter and now his extended family aim to see the project through. Dempsey got it all under way with an Open Day that saw more than 200 people come in through the gates of Kilkeaskin House.

“I knew John almost all my life. I worked with him in Homer Scott’s. He was a great character. He was a great man to do anything bar work. And a great man for the one-liners. Very funny. I used go and visit John – not as much as maybe Conor O’Dwyer and some of the lads, who were very good to him. Myself and Genie went over when they got married. We’d a very good evening.

“They gave him two weeks in June. He said ‘What can I do?’ but he lived until February. The lads were slagging him. ‘You’re taking the piss now!’ The people who turned out at the funeral… He had a lot of friends. He was so popular.”

Meanwhile, he will ride this current wave for as long as he can, using the same basic principle. The gamble of leaving somewhere safe to aim big appears to be paying off but the eye remains firmly on the ball.

“You’re starting from scratch again. You come out of there”, he says, nodding his head up the road towards his former premises and home, “comfortable and you go back to having nothing. People said ‘Look at the place you have’. You just have to work.”

For details on the John Shortt Legends Day and to see list of items available to auction on the day (including 12 months training fees with Jessica Harrington and Michael Halford, trips to the Cheltenham Festival and Dubai World Cup, nominations to a variety of stallions and a fourball with AP McCoy and Ruby Walsh among other attractive lots) go to https://www.punchestown.com/racing/john-shortt-legends-day/.