Bossman Jack

And Bossman Jack is. The six-year-old has won 3 of his last 6 races — a 50% win rate, meaning he crosses the line first every other time he competes. That is a remarkable return at any level. Across his entire career of just six races, he has won 3 and placed on 4 occasions, finishing out of the top three only once. He has barely put a foot wrong.

What is particularly striking is how quickly he has improved. His first career win only came at Wincanton in January 2025, but since then he has accelerated sharply. Skelton has spoken openly about how much Bossman Jack stepped forward on his first run of this season, winning well at Ffos Las and then following that up with another victory at Chepstow in February 2026. The trainer describes everything at home as very positive and says there could be plenty more to come — words that carry weight when they come from a yard operating at this volume and quality.

He handles wet and muddy ground well, which matters in the British winter, and Skelton considers him a likely runner next time out. His recent form reading — a win, then a win, then a blank, then another win — suggests a horse who performs at a high level more often than not, with only one unexplained blip in an otherwise consistent sequence.

Currently racing at Class 4 level, which sits in the middle tier of British racing, Bossman Jack has won 2 of his 4 races at that grade. The natural question now is whether the team will try him in tougher company. Given how confidently Skelton talks about him, and how quickly he has improved since his first win just over a year ago, that step up might not be far away.