St Leger hero Highwayman will take on the best stayers in Europe on Saturday after Joseph O’Brien supplemented him for the British Champions Long Distance Cup at Ascot. Connections paid £37,500 to add him to the two-mile Group 1 on Monday, having decided against a trip to Australia for the Melbourne Cup.
He will have plenty to prove against the likes of Gold Cup winner Scandinavia and Prix du Cadran hero Caballo De Mar, and history is not on his side either. Here is everything you need to know about the Classic winner before Saturday.
From 250/1 maiden to Classic winner
Few Classic winners have come from as far back as Highwayman. Unraced at two, the son of Persian King made little impression in his first four starts over sprint trips and a mile this season, and he was sent off at 250/1 when only eighth in a maiden at Naas in June. That was the last time he was beaten.
Stepped up to a mile and three furlongs at Killarney in July, he won his maiden easily at 5/2. He then took the Listed Vinnie Roe Stakes at Leopardstown at 22/1 in August, before landing the St Leger at Doncaster at 11/1. Under Saffie Osborne, he led going well over two furlongs out and, despite hanging right in the closing stages, beat stablemate Enceladus by two-and-a-half lengths. In the process, Osborne became the first woman to ride the winner of a British Classic. His official rating has soared from 76 to 117 since July, with the St Leger alone earning him a 16lb rise.
What connections say
O’Brien is not getting carried away about the task ahead. “He’s had a good preparation. I’m happy with him and he’s trained well since Doncaster,” he said. “It’s a step up to go against the older horses and up further in distance. Hopefully, he can cope with it.”
There is also a change in the saddle. Stable jockey Dylan Browne McMonagle, who rode Highwayman to his Killarney success, returned from injury at Roscommon on Monday and is set to take over from Osborne. “He’s been off for a while now, so it’s great for him and for us to have him back,” O’Brien added.
History is against the three-year-olds
The biggest obstacle for Highwayman may be his age. No three-year-old has won the Long Distance Cup since it became part of British Champions Day in 2011. In that time, 22 have tried and only five have made the frame, with Tashkhan’s shock second at 50/1 in 2021 the closest any of them have come. By contrast, older horses have won with 15 of their 122 runners.
The last St Leger winner to try was Eldar Eldarov, who could only finish seventh at 11/4 in 2022. Even the great Stradivarius was beaten as a three-year-old, finishing third in 2017 before winning the race the following year. Kew Gardens followed a similar path, winning the St Leger in 2018 and then the Long Distance Cup at four. Highwayman will receive 7lb from his elders, carrying 9st 2lb, but that has not been enough to bridge the gap for his predecessors.
His chances on Saturday
Stamina is another question mark, as Highwayman has never raced beyond the St Leger trip of a mile and six-and-a-half furlongs, and his sire Persian King was a top-class miler. That said, he has improved with every step up in distance so far, and he was still running on strongly at the line at Doncaster.
Historically and on the trends, Highwayman looks up against it. Scandinavia beat everything bar Caballo De Mar in the Cadran and has already won the Gold Cup at Ascot, so the three-year-old would need another big step forward to win. However, few horses have improved as quickly as Highwayman this season, and he is unlikely to be far away.
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