Godolphin's Encke (25-1) spoiled Camelot's Triple Crown bid in the Ladbrokes St Leger at Doncaster.
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Ballydoyle's red-hot 2-5 favourite was tucked in at the back of the pack as the field made their way around Town Moor and he had just two rivals behind him as they turned for home.
Joseph O'Brien still seemed have plenty of horse under him but needed a gap - which eventually appeared with two furlongs to run.
But Encke had stolen a march under Mickael Barzalona as Camelot went in pursuit under pressure from the distance.
He closed all the way to the line but only managed to get to within three-parts-of-a length as Encke claimed the final English classic of the season with Michelangelo (10-1) back in third.
Trainer Aidan O'Brien said: "It wasn't what we thought it was going to be. It was a steadily-run race and Joseph said he was a little bit fresh with him, but that was probably always going to happen in a slowly-run race.
"You have to take your time on him over a mile and six which he (Joseph) did and when he got out he just stayed on rather than quickened.
"In the Guineas he quickened and in the Derby he quickened, but he just stayed on here.
"He ran a great race but just got beat. It's disappointing for everybody but that's the way it is. That's racing.
"We expected him to win and if I thought they were going to go that steady I would have had a pacemaker in or two pacemakers. But that's my fault.
"I was sure they were going to go a pace, but that's the way it was.''
Godolphin racing manager Simon Crisford heaped praise on Barzalona as Sheikh Mohammed's operation won the Leger for the sixth time.
He said: "It's absolutely fantastic. This is a robust horse and we put a line through his run at York (defeat in the Great Voltigeur). The pace was so slow that day and it was falsely-run race.
"Mahmood had been very happy with his work in the build-up to the Leger and Sheikh Mohammed gave the green light to run him.
"Mickael rode a beautiful race and when he kicked at the two-pole he put the race to bed really.
"We weren't sure about his stamina going into the race but he's quite stoutly bred, so we thought it wouldn't be a problem.
"What we loved about that race was the turn of foot he showed, that stands very well for next season and he will stay in training.
"I would imagine it's very unlikely (that he will run again this season) but we will see what Sheikh Mohammed wants to do."
Gosden, responsible for the Michelangelo and also sixth-placed Thought Worthy, said : "The ground dried up too much for Thought Worthy. If the race had been run on Wednesday he would have been a lot closer.
"The other horse (Michelangelo) has finished strongly to get third. The favourite got a little bit trapped.
"Our pacemaker (Dartford) set a nice even gallop. There was no point going off like a lunatic because they know you're only rated 70-something.
"Thought Worthy was in a great position but hated the ground."