It’s not a matter of if but when Aidan O’Brien will become the all-time leading trainer of Epsom Derby (G1) winners. The Coolmore maestro is currently in a four-way tie for first with seven victories and, unsurprisingly, he’s taking six shots in a field of 16 for Saturday’s delayed renewal over Epsom’s famed and undulating 1 1/2-mile course.

If O’Brien’s last couple of wins in the “Blue Riband” suggest anything, it’s to think a little outside the box when sizing up his entries. In 2017 Wings of Eagles shocked the racing world (and perhaps connections themselves) with a tremendous rally from the back of the pack at odds of 40-1. Last year, Anthony Van Dyck narrowly bested his more fancied stablemate Sir Dragonet and others.

I admit to drinking the Kool-Aid last year on Sir Dragonet, who had been unraced at two but turned in a tremendous victory in the Chester Vase (G3). The more experienced Anthony Van Dyck should have been held in higher estimation after easily passing my personal eye test winning the Lingfield Derby Trial.

O’Brien has neither of the top two betting favorites on Saturday. Those are Lingfield Derby Trial winner #3 English King (2-1) and 2000 Guineas (G1) victor #6 Kameko (7-2). There’s not much going against English King — his performance at Lingfield was eye-catching and Frankie Dettori is up this time. The primary downside is that it’s hard to take such a short price in what is a seemingly wide-open Derby. The true abilities of these horses is clouded by the fact racing resumed in England and Ireland only within the last five weeks and reasonable comparisons are somewhat murky given the limited evidence available.

Kameko won what is considered a hot renewal of the Guineas, although some of the ratings I’ve seen for the race seem a bit inflated. I could be wrong, but I just don’t see this horse as being the second coming of a Dancing Brave or Sea the Stars. Despite being a son of Kitten’s Joy, he’s also not guaranteed to stay a mile and a half.

Which brings us back to the O’Brien contingent. #9 Mogul (5-1) has been considered their top Derby prospect for a while and Ryan Moore stays faithful even after the colt metaphorically stubbed his toe with a dull run in the King Edward VII (G2) at Royal Ascot. #13 Russian Emperor (6-1), meanwhile, looked a more exciting contender with a rallying win in the 1 1/4-mile Hampton Court (G3) at the Royal meeting.

Another O’Brien horse of note is #15 VATICAN CITY (8-1), our top pick. By Galileo, he’s out of a Group 2-winning full sister to Giant’s Causeway that’s already produced classic winners Gleneagles and Marvellous, as well as Group 1 winner Happily. Indeed, all six of You’resothrilling’s foals to race have won or placed at the top level.

As kin to Gleneagles, Marvellous, and Happily, there is some debate whether Vatican City will stay farther than, say, 1 1/4 miles. At a price hovering around 10-1, I’ll take a chance he does following a strong-second place effort in the Irish 2000 Guineas (G1) when he lacked a clear path at a crucial point in the stretch and fell 1 3/4 lengths short of the talented Siskin. Vatican City should improve for the run and is an exciting prospect under Padraig Beggy, who patiently and brilliantly guided Wings of Eagles three years ago.

In Exacta wagers, I’ll also use English King, Russian Emperor, and #2 Emissary (30-1).