O’Brien’s mastery, big-spending Joorabchian: Derby contenders jostle for position

As a snapshot of the early state of play in the 2025 Flat season, the field for the Dante Stakes at York on Thursday, the last recognised trial for the Derby at Epsom on 7 June, promises to be pin-sharp. Aidan O’Brien will be hoping to complete an unprecedented clean sweep of the five major trials for the Derby at Epsom with the current ante-post favourite for the Classic, The Lion In Winter. Charlie Appleby, fresh from a double in the 2,000 Guineas and 1,000 Guineas at Newmarket, has supplemented the unbeaten Alpine Trail.

Andrew Balding, the early leader in the trainers’ title race, has the current third-favourite, Royal Playwright, while football super-agent Kia Joorabchian’s Amo Racing operation, in its first season based at the famous Freemason Lodge yard in Newmarket, fields Tuscan Hills, an unbeaten grandson of an Oaks winner.

The reappearance of a long-term favourite for the Derby in Britain’s most significant trial is always a moment to savour, but the fact that O’Brien has won the previous four adds an extra dimension to Thursday’s contest.

His dominance at Chester, Lingfield and Leopardstown is not unprecedented, as he also hoovered up the Chester Vase and the Dee Stakes, and the Derby Trials at Lingfield and Leopardstown in 2013, 2019 and 2022.

His Dante runners in those years, though, were not seen as potential Ballydoyle first-strings for Epsom. Only one, in fact, even set off as the favourite, and that was a swiftly forgotten twice-raced maiden winner, Indian Chief, who finished third in the 2013 Dante, and required 21 subsequent starts and two changes of stable before finally adding to his win tally, off a mark of 65 at Chepstow in 2016.

Alpine Trail, trained by in-form Charlie Appleby, faces Derby favourite The Lion in Winter at York this week. Photograph: David Davies/PA

The Lion In Winter is a very different proposition, having been on top of the Derby betting since his win in the Acomb Stakes at York last August, with Ruling Court, this year’s 2,000 Guineas winner and current Derby second-favourite, back in third. He was as short as 6-1 for Epsom at that early stage of his career, and despite not having seen a racecourse since, The Lion In Winter is now no bigger than 3-1 to give his trainer a record-extending 11th win in the Derby.

In a year when, uniquely, the reigning champion trainers both on the Flat and over jumps in Britain are both based in Ireland, the impression that O’Brien has saved his best Derby contender for last seems to fit with an overall narrative of increasing Irish dominance under both codes.

But the memory of O’Brien’s most recent Dante favourite – in fact, his only Dante favourite since Indian Chief – offers at least a little encouragement for The Lion In Winter’s opponents on Thursday. Like The Lion In Winter, High Definition arrived on the Knavesmire having won his two starts as a juvenile and spent the winter at the head of the Derby betting. He set off at 13-8, finished third – and then, 11 races and as many defeats later, finally got another win on the board a few days short of his fifth birthday, in a maiden hurdle at Leopardstown.

If The Lion In Winter fails to live up to expectations on Thursday, there are several interesting candidates in the lineup that could yet head to Epsom as serious contenders for the Derby, and none more so, perhaps, than Raphael Freire’s Tuscan Hills.

Freire has had a solid start to his time at Freemason Lodge, with four wins from 22 runners so far, but Celestial King, Amo’s sale-topping £1.75m purchase at the Newmarket breeze-ups in April, was only fourth on debut at Ascot on Saturday, when he faded to finish nearly six lengths behind the winner.

Joorabchian has already seen his colours carried into second place aboard big outsiders in the Derby in both 2021, when Mojo Star, at 50-1, was four and a half lengths behind Adayar, and 2023, when King Of Steel, at 66-1, was just a half length behind Auguste Rodin.

In an apparent partnership with Evangelos Marinakis – most recently seen venting his spleen at Nottingham Forest manager Nuno Espírito Santo, after his side conceded a late equaliser against Leicester on Sunday – Joorabchian has been on a spectacular spending spree ever since last October’s Book One sale at Tattersalls in Newmarket, where he went bid-for-bid with Sheikh Mohammed, no less, over a series of seven-figure yearlings.

He snapped up Freemason Lodge after Sir Michael Stoute announced his retirement, was busy in the market again at the December foal sale in Newmarket, where he paid 2.5m gns (£2.63m) for a sister to Chaldean, the 2023 2,000 Guineas winner, and splashed out a further 3.2m gns (£3.3m) on seven lots – including Celestial King – at the breeze-ups.

There have been enough hirings, firings – and re-hirings – in Amo Racing’s relatively brief existence to date to suggest that Joorabchian will be expecting some tangible return on his investment in the not-too-distant future. A big run from Tuscan Hills on Thursday would be timely, to say the least.