His dam Rhadegunda showed good form on the track winning three races including the Listed Prix Solitude, and has had some success as a broodmare, producing the Solario Stakes winner Fantastic Moon.
Other descendants of On the House's grand-dam Courtessa have included Golden Horn, Rebecca Sharp, Habibti and the Australian champions Danewin and Octagonal.
Ridden by Robert Havlin he raced towards the rear of the ten-runner field before taking the lead inside the final furlong and winning by one and a quarter lengths from the Godolphin runner Wild Tempest.
[4] Cracksman began his second season in the Investec Derby Trial over ten furlongs at Epsom Racecourse on 26 April, a race in which he was ridden for the first time by Frankie Dettori.
After struggling to obtain a clear run early in the straight and then finished strongly to catch the Mark Johnston-trained Permian on the line and win by a short head.
On 1 July at the Curragh he faced Wings of Eagles again in the Irish Derby, a race which also attracted the leading French colt Waldgeist.
After being restrained in the early stages he made good progress in the straight but failed by a neck to overhaul the front-running Capri with the Derby winner a short head away in third.
With Dettori in the saddle he went to the front early in the straight and steadily increased his advantage to come home six lengths clear of the Chester Vase winner Venice Beach.
[8] Oppenheimer opted not to run his colt in the Arc citing the unsuitability of the Chantilly track and his desire to save Cracksman for a four-year-old campaign.
[9] On 21 October Cracksman was brought back in distance and was matched against older horses for the first time in the Champion Stakes over ten furlongs at Ascot Racecourse.
With Dettori again in the saddle he was made the 13/8 favourite in a ten-runner field which included Highland Reel, Cliffs of Moher, Barney Roy, Brametot, Poet's Word and Recoletos (Prix Greffulhe).
After racing in fourth place until the final turn, Cracksman went to the front early in the straight and drew away from his opponents to win in "impressive" style by seven lengths from Poet's Word.
"[12] Cracksman began his third campaign in the Prix Ganay at the newly re-opened Longchamp Racecourse on 29 April as 3/5 favourite against six opponents, including Cloth of Stars and Rhododendron.
Later he explained that the colt had lunged forward in the starting stalls, struck his head hard against the framework and "must have run the race in a complete daze".
After being settled in fourth place, he took the lead approaching the last quarter mile and drew right away to win by six lengths from Crystal Ocean, with Dettori waving his whip to the crowd in celebration.