His first win came at Listowel in September 2025, and jockey John Gleason came away genuinely excited. He described Mister Pessimistic as travelling strongly throughout and winning well — the kind of performance that makes a yard sit up and take notice. Gleason noted that the team had already liked what they saw at home, that he had won a point-to-point race smoothly, and that his breeding suggested he would get better with longer distances. Crucially, Gleason flagged that jumping hurdles — putting an obstacle in front of him — was likely to bring out even more improvement. That is a big statement about a horse who had not yet had the chance to prove it.
He proved it quickly. In November 2025, Mister Pessimistic won again at Cork, this time over hurdles, on his very first attempt at the discipline. Trainer Henry De Bromhead, one of Ireland's most respected handlers and a man whose yard has sent out 107 winners this season alone, described it as a good win and noted that the horse remains unbeaten over hurdles. De Bromhead had been pointing him towards a novice hurdle at Leopardstown over Christmas — one of the most prestigious tracks in Ireland — as the next step up in class.
What makes the recent form figures slightly harder to read is that his last three runs, recorded as eighth, ninth, and sixth, came after those two wins. Those results need context — if those runs came at a significantly higher level of competition, as the Leopardstown ambition would suggest, finishing mid-field tells a different story than simply going backwards. Either way, De Bromhead is not a trainer who runs horses without a plan, and a yard operating at 107 winners in a season is one firing on all cylinders. Mister Pessimistic arrived with promise, delivered when asked, and has plenty of road left to travel.
| Course | Races | Results | Last visited | Win rate |
|---|---|---|---|---|
| Leopardstown Galloping |
2 | 2 other | 1 Feb | 0% |
| Cork Galloping |
1 | 1 win | 2 Nov | 100% |
| Listowel Sharp |
1 | 1 win | 25 Sep | 100% |
| Punchestown Galloping |
1 | 1 other | 29 Apr | 0% |