Joseph O'Brien gave Imperial Monarch a fine ride to land the bet365 Classic Trial at Sandown.
The young son of trainer Aidan O'Brien decided to take his mount (11-8 favourite) away from his three rivals and steer a wide course under the trees.
With five lengths to find turning for home, it initially looked as if O'Brien Jnr had made a costly error, however his willing mount picked up well passing the bushes and in the end won a shade cosily.
John Gosden's Thought Worthy (9-2) cut out most of the early running and stayed on well for second, ahead of rivals Rougemont and Stipulate.
O'Brien jnr told Racing UK: "We had a look at the wide outside and it was nicer ground out there. There are tyre tracks all the way round and the ground is much more compact.
"The ground is bottomless down the inside and barely raceable.
"I was very happy where I was. I was a good six or eight lengths back turning in but I was very happy where I was.
"Me, my dad and Paul Smith (owner's representative) discussed it in the parade ring and we decided to take the chance.
"He's a nice horse. I was saving a lot of energy and I was travelling a lot better than those on the inside.
"At home he's easy to ride and very uncomplicated. He covers a lot of ground and has a good action."