Dan Skelton trains him out of Alcester in Warwickshire, and if you need a reference point for how good that yard is right now, consider this: they've sent out 194 winners in the current season alone. This is one of the busiest and most successful operations in British racing, and when Skelton singles a horse out as one he's always held in high regard, that means something. He's spoken glowingly about Bossman Jack's progress, noting that the horse stepped forward significantly on his first run back this season and then improved again next time out — two consecutive jumps in form is exactly what you want to see from a young horse still finding his ceiling.
That ceiling may be some way off yet. He began his career with a win at Wincanton in January 2025, and his most recent success came at Aintree just this week — a famous old track that puts a premium on jumping ability and jumping confidence. Winning there is never a formality. Looking at his last six races, he's won three of them, including a blank run in the mix, which makes his overall consistency even more striking.
He's been competing mostly at Class 4, winning 2 of his 4 races at that level — half of them — but Skelton has hinted that there's more to come, and horses who win at this kind of rate tend to find themselves pointed at better company before long. His trainer has also flagged that he handles wet, muddy ground especially well, which gives the team options when the weather turns. At six years old, he's just entering the prime of his career. The interesting question is how far they decide to push him.
| Course | Races | Results | Last visited | Win rate |
|---|---|---|---|---|
| Ffos Las Galloping |
1 | 1 win | 8 Jan | 100% |
| Aintree Galloping |
1 | 1 win | 11 Apr | 100% |
| Wincanton Galloping |
1 | 1 win | 16 Jan | 100% |
| Chepstow Galloping |
1 | 1 win | 13 Feb | 100% |
| Wetherby Galloping |
1 | 1 other | 11 Feb | 0% |
| Warwick Sharp |
1 | 1 third | 20 Nov | 0% |
| Cheltenham Galloping |
1 | 1 other | 11 Mar | 0% |