Freewheelin Dylan at Kilbeggan: The Complete Story

Freewheelin Dylan is an Irish-bred bay gelding, foaled in 2012. He is by Curtain Time out of the mare Gaye Future, who was by Beat All, and he was bred by Liam Norris of Dungarvan. Throughout his racing life he was owned by Sheila Mangan, who works in the yard of his trainer, Dermot A McLoughlin, near Fairyhouse in Co. Meath. That closeness between owner, trainer and yard is part of what made his big days feel like small-team wins rather than the work of a major operation.

Like many Irish jumpers, he learned his trade between the flags before going under Rules. He won twice in point-to-points, then made the switch to track racing, where his record came to include six chase wins in Ireland. He was not a flashy, high-class chaser by profile. He was a genuine, hard-galloping handicapper, the sort who wins by being brave and relentless from the front rather than by producing a turn of foot.

That running style matters to the Kilbeggan story. A horse who wants to make all and keep finding under pressure is exactly the type the sharp Kilbeggan circuit rewards, and it was the same set of qualities that later carried him round three and a half miles of Fairyhouse without ever seeing another rival's head in front.

The making-all handicapper

Freewheelin Dylan's whole approach was built on stamina and front-running. He asked opponents to come and catch him, and over staying trips that is a difficult thing to do to a horse who keeps galloping. In the 2020 Midlands National at Kilbeggan he made every yard off a mark of 135 and held on by the minimum margin. That was not a fluke of tactics; it was who he was.

His trainer's own background sits behind the story. Dermot McLoughlin's late father, Liam, rode the 1962 Irish Grand National winner Kerforo and was the first jockey ever to ride the great Arkle. The family's connection to the Irish National ran deep long before Freewheelin Dylan added to it.

The Fairyhouse shock, in context

Freewheelin Dylan's defining day did not come at Kilbeggan. On Easter Monday, 5 April 2021, he won the BoyleSports Irish Grand National at Fairyhouse at 150/1 under Ricky Doyle, making all over three miles five furlongs and holding Run Wild Fred by a length and a quarter. He became the longest-priced winner in the history of the race, which was first run in 1870, and landed a winner's prize reported at €216,000. It remains one of the biggest shocks the race has produced.

That win happened at Fairyhouse, not Kilbeggan, and it belongs here only as the wider career context that makes his Kilbeggan summer so notable. The course-bound part of his story, the racing he actually did at Kilbeggan, is covered in the next section.

Freewheelin Dylan's defining Kilbeggan day was the 2020 Midlands National. It is the run that ties him to the course and the one that set up everything that followed. Kilbeggan's managing director, Paddy Dunican, later described him as "a bit of a Kilbeggan specialist, having won here three times already," so he was clearly a familiar face at the track. The full detail of those earlier wins is not confirmed here, so this section stays with the race that is fully documented: the 2020 Midlands National.

The 2020 Midlands National

The Midlands National is Kilbeggan's flagship handicap chase, run each July over about three miles one furlong, a stamina test over sixteen fences on a sharp, turning circuit. In 2020 it was run on 10 July as the AXA Farm Insurance Midlands National, behind closed doors during the pandemic, so the drama played out in near silence.

Freewheelin Dylan, carrying a mark of 135 and ridden by Ricky Doyle, was sent off at 11/1. He did what he always did and went straight to the front. From there he dictated, kept finding at his fences, and asked the chasers behind him to prove they could get past. In a desperately tight finish he held on by a nose from Three Musketeers, ridden by Davy Russell, with the Gordon Elliott-trained Swingbridge a 50/1 third.

The result did not go through unremarked. The stewards held an interference enquiry into the finish. The judge's placings were left unaltered, so Freewheelin Dylan kept the race, but Russell was suspended for careless riding. The bare result stood, and the winner had booked his summer.

His Kilbeggan record, as documented, reads:

Year	Race	Distance	Weight	SP	Jockey	Result
2020	Midlands National (AXA Farm Insurance)	3m1f	11-2	11/1	Ricky Doyle	Won, by a nose

Why the track suited him

Kilbeggan is a sharp, right-handed circuit of around nine furlongs, with a turn after the penultimate fence and a short, uphill run-in of roughly 300 yards. It favours handy, speedy front-runners and accurate jumpers over long-striding gallopers who need room to build up speed. A horse who can lead, jump economically and keep going up the final climb is in his element.

That is a fair description of Freewheelin Dylan. His whole method was to make all and keep galloping, and the Midlands National asked exactly those questions. Winning it off a mark of 135, by the minimum margin, in a stewards' enquiry finish, told you he had the courage and the stamina to win a staying handicap by refusing to give in. It was the clearest possible pointer to the bigger staying test he would pass at Fairyhouse nine months later. That later win, though, came at Fairyhouse and forms no part of his Kilbeggan record.

Freewheelin Dylan's Kilbeggan story really comes down to a handful of minutes in July 2020, and to one image in particular: a front-runner with nothing left to give still refusing to be caught on the line.

The nose on the line

The 2020 Midlands National was decided by the smallest margin in racing. Freewheelin Dylan had led from the start, and by the final fences the question was simple: could anyone reel him in. Three Musketeers, under Davy Russell, threw down the challenge on the run to the line. Freewheelin Dylan would not stop. He held on by a nose.

A nose is the sort of result that can turn on a single stride, and this one came with a sting: the stewards looked hard at the finish. When they left the placings alone, the winner kept the race he had led throughout. For a horse whose only weapon was his own stubbornness in front, holding on by the minimum from a rider as strong as Russell was the truest expression of what he was.

The making-all masterclass

The defining feature of the day was not a burst of speed. It was the absence of one. Freewheelin Dylan did not need to quicken because he never let the race come back to him. Off a mark of 135, he set his own pace, jumped for fun on Kilbeggan's turning track, and made his rivals do all the chasing over three miles one furlong.

Making all in a big-field handicap chase takes a particular sort of nerve, from horse and rider alike. Ricky Doyle judged the fractions so that there was just enough left for the climb to the line, and Freewheelin Dylan found exactly that much and no more. On a sharp course that punishes any hesitation into the fences, it was a front-running ride carried off in near silence behind closed gates.

The springboard

The lasting significance of the day is what it pointed towards. A brave, all-the-way win off 135 in a valuable summer handicap was the evidence that Freewheelin Dylan could carry his stamina and his front-running into the biggest staying handicaps of the year. Nine months later, at Fairyhouse, he did precisely that, at 150/1. That win came elsewhere, but the Kilbeggan afternoon in July 2020 was where the racing world got its first real look at the horse who would produce it.

Kilbeggan has no single champion who towers over its history the way Arkle or Red Rum define other tracks. Its story is told instead through course specialists and staging posts, horses who won there often and horses who passed through on the way to fame elsewhere. Freewheelin Dylan matters because he links the small midlands handicap to the biggest staying prize in the Irish jumps calendar.

What his win proved

The lasting value of the 2020 Midlands National is the line it draws from Kilbeggan to Fairyhouse. A brave, all-the-way handicap winner off 135 in July became the 150/1 Irish Grand National winner the following April, the longest-priced winner in the history of a race first run in 1870. It is a reminder that a summer handicap at a jumps-only country track can be a real trial for the sport's marquee staying handicaps, not just a local occasion. For punters, the moral is that the horse who wins ugly and refuses to stop over a stiff Kilbeggan trip is worth remembering when the big-field nationals come round.

The company he keeps at Kilbeggan

Freewheelin Dylan sits within a small cast of horses the track is proud to claim, and it is worth being clear about who was what.

The genuine Kilbeggan course specialist among the recent names is Pakens Rock, a gelding who won three times at the track across both fences and hurdles. His trainer put it plainly after his 2025 win: "He likes it here." Repeated wins on the tight, turning circuit are the mark of a true course horse, and Pakens Rock earned that label.

Two of the biggest names merely passed through. Tiger Roll, later a dual Aintree Grand National winner and a five-time Cheltenham Festival scorer, won a novice chase at Kilbeggan in June 2016 as an early-career staging post, when the track was his owner Gigginstown's local course. Cause of Causes, who went on to win three times at the Cheltenham Festival, recorded an early win at Kilbeggan in 2012 before being sold on. Neither was a Kilbeggan specialist; the track was simply an early rung on the ladder.

Freewheelin Dylan falls between the two groups. He was a familiar Kilbeggan face, described by the racecourse's managing director as "a bit of a Kilbeggan specialist," and his 2020 Midlands National is the fully documented win that ties him to the place. Unlike Tiger Roll and Cause of Causes, he did not go on to fame at Cheltenham or Aintree. His fame came at Fairyhouse, and Kilbeggan was where the run to it began.

That is the verdict worth leaving with. Kilbeggan's honour roll is not built on a single legend. It is built on the honest, hard-galloping types the sharp circuit rewards, and Freewheelin Dylan, the nose-margin summer winner who became racing's biggest-priced national shock, is one of the best modern examples of what a Kilbeggan handicap can lead to.