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Tommy, how's you Phelan?

Updated: Jan 9

The Racing Life of Ex-Jockey Tommy Phelan

'It’s all non-stop at the moment but that’s part and parcel of the job,’ says the cheerful ex-jockey Tommy Phelan, describing his position of head lad for top trainer Donald McCain. There’s lots of banter, such as saying that he’s ‘pushing on now a bit’ about the age of 43; there’s laughter and stories too – a love of horseracing that runs deeply through his veins.

Growing up in Ballynonty, near Killenaule, in rural County Tipperary, right where Edward O’Grady trains, Tommy explains that his father worked for there for thirty-seven years. ‘One summer, my mum suggested I got a job – I wasn’t sure where to go so she suggested I went to Edward O’Grady’s,’ he explains. ‘Tommy Ryan was the head man at the time and he said come in – the rest is history; that’s how I started in racing.’

A move to Jonjo O’Neill’s brought Tommy over here to cold Cumbria and then to Gloucestershire. ‘I remember the phone signal was non-existent at Jackdaws Castle. We’d be sticking our heads out through the skylights of the top flats and still getting zero.’ Tommy chuckles and laughs – the vivid memories bouncing back and forth: people, names, places and horses – every one of them golden and warm.

Tommy, lives ten minutes from Donald McCain's yard in Whitchurch, Shropshire with Andi, his fiancée of eight years and their three dogs Mindi, Ozzy and Tilly.

Did you have a childhood? I had ponies and first sat on a pony at six years of age. Obviously, back home in Ireland, you get on, give it a kick in the belly and just go. My dad was tough but always fair, giving me advice and helping me as much as he could but he'd also let me get on with it and hoped for the best.

How did you get into racing? My dad was in racing all his life and I couldn't learn as well from anyone else as I did him but he passed away when I was eleven on Edward O’Grady’s gallops – he had a massive heart attack on one of the horses. When that happened, I lost interest in racing for about three years – I didn't do my pony or anything until about 1995, when I got back into riding. I rode on an old hunter and then I started riding racehorses in Edward O’Grady’s.

Do you have a key memory of riding out as a boy? My idol was Richard Dunwoody – he used to ride Sound Man for Edward O'Grady and go up against Viking Flagship and all the other good horses at the time. One morning, this man arrived carrying his helmet and it was Richard Dunwoody. I was about fifteen and like ‘Oh my God, Richard Dunwoody’s just walked in’. A bit later on, the string was walking up to the grass gallop in two rows of about ten; I was riding a lovely little mare, a darling of a thing and Edward O'Grady was saying his usual ‘You go with him, you go with him, you go with him’. And he said to me, ‘You go with Richard’. I had the biggest grin of my life and couldn’t believe that Richard was talking to me and I was like, ‘what do I do or say?’ Just to ride work once with the man was unbelievable.

I got a bollocking that morning as well – Edward O'Grady was a good fair man but he'd let me know if I'd done something wrong. When I was pulling up, he demanded, ‘What did you do in the first furlong?’ But I didn't know what I’d done because I was riding beside Richard Dunwoody. ‘Jeese,’ I muttered, ‘I don't know Mr O’Grady.’ ‘You got a head in front of him,’ he retorted. He always used to say if horses fell back, you'd go forward and keep on working but I weighed about five stone and was working all over Richard Dunwoody and I'd pulled up with an even bigger grin on my face. After, Mr O’Grady pointed out that I’d headed Richard, I went from being on cloud nine to rock bottom in a few seconds. Yet, Richard came up besides me and said, ‘That was perfect, Tom.’

Tommy winning on Sherkin Island at Uttoxeter in January 2004

How did you come over to ride in the UK? In ‘96, I went to the apprentice school called RACE in Kildare for ten months. Then, I went straight out to Frank Berry’s and I absolutely loved every minute. If he was still training now then I'd still be there. Yet, he got the job as JP McManus’ racing manager and it was Frank who said, ‘Do you fancy going to England to Jonjo O'Neill's?’. I’d gone racing to England with horses at Frank’s so I thought I'd give it a go but thought I'd be back in a year's time. In November 2000, I moved to Carlisle straight after the Paddy Power meeting at Cheltenham, before Jonjo made the big move to Jackdaws Castle about eight months later.

I had my first ride a month later on Boxing Day on a horse called Creon who was owned by JP McManus. We won round Wetherby and I stayed at Jonjo’s for six years after that.

Is it true you lead up a Cheltenham Festival winner? I was very very lucky – I looked after Iris’s Gift, I never sat on him but he won the Stayer’s in ‘04 and I led him up. Even though I was busy race riding at the time, it was the only chance I got of going into the winner's enclosure at the Festival – it was a golden moment for me to go with him. When he got beaten by Barracuda the year before as a novice, Jonjo, myself and Rob Lester, who owned him, were also absolutely gutted – at that time, we used to have twenty runners going to Cheltenham.

The next year, I was meant to be going up to Fakenham to have a ride so I rang my agent Dave Roberts, saying that I couldn't ride it as I’d done my shoulder so that’s how I ended up going to Cheltenham to lead up Iris’s Gift. I was never lucky enough to ride a Festival winner as a jockey, I got to ride into the winner's enclosure on placed horses but that was a highlight of my racing life.

That second time, when Barry Geraghty was legged up on Iris's Gift – he asked me ‘What do you think?’ I insisted he just kicked on. ‘I was thinking the same,’ he answered. ‘They won't catch you,’ I replied. The had the revenge of coming back and beating Barracuda. It was a great day for the yard – I was lucky enough to look after Creon too who won the Pertemps Final the day before.

I still see Jonjo and text or ring him, always have a laugh – he was a great man to me, looked after me as a jockey and I had a lot of winners for Jonjo. Without him, I wouldn't have been here very long – he's a brilliant man and a great boss.

What were your highlight of working on that yard? At the time, there were really really good lads and good riders. Liam Cooper started settling in and getting many opportunities riding, ending up as stable jockey. He was a brilliant horseman; absolutely class over fence or a hurdle and a really nice lad from a nice family – he’d be brilliant if I ever wanted a bit of advice about a track or a race and so was Jonjo. Richie McGrath was an amateur, Elliott Cooper came along later too – we all moved down south together. Wayne Jones was another one too, Tom Siddall came in and Ben Hitchcock started riding the horses; he won the first bumper on Iris’s Gift at Worcester in the summer.

I remember the competition was healthy – if someone rode a winner today and I was on one tomorrow, then in my head I'd have to ride a winner on that to keep my foot in the door. Obviously in a big yard like that, you'd be wanting to show Jonjo that you were as good as the man beside you but when the other lads rode a winner, you'd be delighted for them too. It was a fun yard with a great atmosphere.

How has racing changed over the years? Racing is changing a lot and it’s scary. Unfortunately, a lot want an easy life and to take the money. And sadly, in this day and age, it's as if history doesn't matter. I'm not saying they don't like looking at the racing and seeing their horses running but if you talk about a horse called Viking Flagship, they go ‘Viking who?’

Think of small trainers, like Oliver Sherwood and what he achieved, and how they are struggling. What's it going to be like in five, ten years’ time? I think racing, especially the BHA, needs waking up big time. I hope I'm wrong and I probably will be wrong but the way things are going in less than ten years’ time, there won't be any small trainers. It'll be all big yards taking each other on.

I've been in the game a long time and I can see the change in it. Even twenty years ago, it was changing but now it's change, change, change – the whip rules and all the watering down of everything. It is a shame because, years ago, the atmosphere used to be always brilliant.

What other roles have you had in racing? After six years at Jonjo’s, things started changing there: AP took the job and opportunities were a little scarce so I moved out and went freelance, going to Heather Dalton's for fourteen months. I rode a lot of winners for her and in 2008-10, I went fully freelance.

I used to ride out at six yards just to keep going – they weren’t big yards but smaller ones that had plenty of horses and winners. An owner I knew called Robert Matthew had a few horses in training at David Bridgewater’s and he said he wanted me to ride them, so Bridgy said come and ride out. I rode out for Bridgy and my first ride was for Robert at Stratford. On the same day, I rode Reg’s Ruby who won and was owned by Bridgy’s mother Mary. The Giant Bolster was a novice chaser at the time so it would have been about 2012 – for two years, I was riding quite a few winners for Bridgy and rode The Giant Bolster round Chepstow in the Totepool Silver Trophy. I also rode Wyck Hill, who was a good horse – I rode him once and won on him at Wetherby.

Photo Credit: Shutterstock

As always in racing, you get to a certain point and you go your different ways but Bridgy and I have kept in touch and we’re good friends. So, I kept freelancing away, riding out for as many yards as I possibly could but in 2017, I lost Dave Roberts as my agent. I had been with him from the start so for about seventeen years – he said things were going quiet so he left it at that. I was a bit like, ‘Oh no, I've got no agent’ but I did get another one and we had a lot of success and a lot of winners together.

Yet, life as a freelance jockey was hard. I had done it for about fifteen years and I was struggling. I eventually moved to Chorley in Lancashire so I rang Donald McCain as there's not many yards round there, especially jump yards. He said to come in and was honest, saying that he couldn't promise me anything. From day one, Donald was always straight down the middle.

I rode out daily, had two rides for Donald and he said to stop being an idiot – come and work for him full time. So, I did – I rode out, helped on the yard – anything they wanted me to do. Alan Bradley, who was head man at the time, wanted an assistant so I took on that role and not long ago, he retired so Donald offered me his position. I've been doing that about twelve weeks – everything changed very quickly.

What type of boss is Donald McCain? Donald is a good man, straight down the middle with you. He wants to go forwards and wants good people around him. AJ Lane as assistant. Ludo Gaubusseau is an A1 head travelling lad and a good man; there are young lads going through the ranks as jockeys. I'm in another good fun yard again, working towards the goal of winners every day.

The best things about being a head lad? At the moment, it's all a bit new to me but I love seeing everyone happy and enjoying the work. I enjoy the care of the horses and seeing the horses all happy. I try and make work fun for everyone.

What's the worst thing about being a head lad? Staff not turning up.

What jockeys do you admire? Obviously, one is AP McCoy; I've seen him take falls no one else would survive. The one day, I saw him have a fall in a hurdle race at Ludlow. As we all passed the stable yard, he fell in front of me and I absolutely kicked the living daylights out of him; I had nowhere to go and all I could hear were groans beneath me. All the rest of the way round, I was thinking that I was after killing AP; the Cheltenham Festival was only about a week away and I thought he was dead.

I came in, asking after AP but he hadn't got back in himself. The next minute, he arrived but couldn't move. He sat down with a cup of tea containing about twenty sugars – he had another ride for Martin Pipe and I thought he wouldn't be riding it but somehow, he got up. His valet Shane had to put the colours on him and button them up and AP pulled himself together, went and rode this horse first time over fences. That will always stick in my mind – there's no way a human should be doing that. He was just a different gravy: schooling, in a race, even near the line, you'd be always thinking where was AP? And he was always there.

Ruby Walsh was a great horseman and amazing and I loved watching Mick Kinane ride on the Flat – he was just a world class jockey but AP McCoy will always be the main man.

What do you remember most about being a jockey? I rode in Ireland on the Flat and National Hunt in over a hundred rides, riding against the best on the Flat, Mick Kinane and Johnny Murtagh. Over jumps, there was Charlie Swan and at the time, Richard Dunwoody was still knocking around.

Over here, Ruby Walsh, AP McCoy and Timmy Murphy were always the best boys. I was very lucky and honoured to be involved with those amazing riders and learned a lot from everyone. When you were in a finish with Timmy, AP, Dickie Johnson, they were only in second gear and I was in sixth gear. When I look back, I was outclassed. They were just proper riders – good lads and good riders. I was lucky to ride in that era.

Best racing party: Jonjo’s Christmas dos. I'll never forget Jonjo doing the Irish Rover after a few, dragging the young ones in and swinging them around.

Best days as a jockey: I rode a few good handicappers, especially at Jonjo’s, a twenty grand handicap on Wyck Hill for Bridgy and I reckon, he was the best horse I've ridden on a racecourse. I rode The Giant Bolster, Geos for Nicky Henderson and I’ll never forget Creon either. I rode good handicappers for Noel Chance as well.

Favourite meal: I love spaghetti bolognese.

Favourite drink: I'm partial to Guinness.

Favourite snack: I love Twirls.

Favourite holiday destination: I have to say home – home is where the heart is.

Favourite film: I love true stories so it's Catch Me If You Can.

Favourite music: I like U2.

Ideal day off: Just chilling out with the missus and all that.

*Many thanks to Old Gold Racing for the help in securing this interview. They published it first in their fabulous newsletter Racing Weekly. To sign up, go to

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