Looks Like Trouble was a highly talented, if fragile, steeplechaser trained by Noel Chance, famous for winning the Cheltenham Gold Cup in 2000. In so doing, he provided Richard Johnson with his first winner of the Blue Riband event.
Although apparently well regarded at home, Looks Like Trouble had looked fairly ordinary in his first half a dozen races over hurdles and fences but, on his seventh start under Rules, belied odds of 20/1 by hacking up in an eventful, but decidedly ordinary, novices’ chase at Doncaster in January, 1999. He followed up in a similar race at Sandown a month later, but proved nothing short of a revelation when pushed clear to win Royal & SunAlliance Chase at the Cheltenham Festival by 30 lengths, albeit aided by the departure of hot favourite Nick Dundee at the third last fence, when travelling ominously well.
Looks Like Trouble began the 1999/2000 season by finishing third, beaten 10 lengths, behind See More Business in the Charlie Hall Chase at Wetherby and was subsequently pulled up behind the same rival, on soft going, in the King George at Kempton. Nevertheless, he won his next start, the Pillar Property Chase at Cheltenham, by a distance and so lined up for the Gold Cup as 9/2 joint second favourite, alongside Florida Pearl and behind old rival, and 9/4 favourite, See More Business.
On good to firm going, with Richard Johnson in the saddle for the first time, he jumped ahead at the last fence and stayed on gamey to beat Florida Pearl by 5 lengths. Noel Chance reflected on the victory, saying, “He was a champion. Unfortunately he’d had a leg problem since before he’d won the SunAlliance and it was only a matter of time before it called a halt to his gallop.”