He believed an older MR BIG could handle the 1,400m trip for the first time and he was proven right.
His reward: His second successive Group 3 Jumbo Jet Trophy, after Super Easy, when Mr Big raced away to land Sunday's $200,000 feature in Race 10 at Kranji.
Pre-race, trainer Michael Freedman had said that it was time his money-spinner, who had won 10 times from 1,000m to 1,200m from 24 starts, to step up his now five-year-old Australian-bred to 1,400m.
Jockey Corey Brown jumped the former Juvenile Champion swiftly and managed to lead by a couple of lengths early from Natural Nice and City Lad, who raced a bit wide.
But the Melbourne Cup-winning Australian rider then eased his mount back a little, which saw City Lad ranging alongside at the 600m mark. They were followed by Natural Nice, the $14 favourite Speedy Cat wide out, Flying Fulton and Running Tall.
City Lad kicked and popped his head in front of Mr Big on straightening but, once shaken by Brown, Mr Big found another gear and broke clear.
Champion jockey Joao Moreira's mount What Now came from worse than midfield to go after the leader. Mr Big's stablemate Nandowra, who was last early in the field of 14, loomed into the picture.
But it was evident that the fast-finishing duo were not going to make it.
Mr Big, who started as the second favourite at $23 for a win, kept up a bright gallop to beat What Now by 2¼ lengths, with a neck to Nandowra. City Lad hung on for fourth, half a length away.
The winner clocked a smart 1min 21.81sec for the 1,400m trip.
It was his first win since he returned from his gallant fifth in the International Group 1 Al Quoz Sprint over 1,000m at Meydan on Dubai World Cup Night.
Between his Dubai run and Sunday, the gelding by Elusive Quality had two seconds, an eighth behind Hong Kong's Lucky Nine in the International Group 1 KrisFlyer International Sprint and a last-start fourth.
Grinning from ear to ear, Freedman said: "I should have tried him over 1,400m a bit earlier. "Yeah, I said to someone during the week, I mean on paper, his form didn't read that well over the last couple of runs. But there were genuine reasons for it.
"You know, when I sat down and thought about whether it was worth trying over this sort of distance, I thought this was the ideal race to do it - back on the short course after not racing on the turf for a while does help on-pacers.
"Corey gave him a lovely ride. You know, when he sort of got left alone for the first 200m, I was really happy and then, obviously, he was taken on a little mid-race but I think, with a horse like him, that actually helps because he's such a competitor.
"He loves being in a bit of a battle and, yeah, it's a big thrill. I mean, he's been an absolute stable stalwart. He's one of the stable favourites and he's racing up in the highest level and that's really satisfying." Now that the O & T Stable-owned Mr Big has come through nicely, it has "opened up a few other opportunities".
"Well, you know, I wouldn't rule out trying over a mile," said Freedman.
"You know, he has certainly run that out pretty well and ran a slick time doing it, so I'll give that a bit of a thought."
Freedman was referring to the Group 1 Panasonic Kranji Mile over 1,600m on Oct 6. Mr Big gave Brown his first winner since he returned from a brief stint in France to resume riding at Kranji.
It was their fourth partnership, having finished second in the Group 1 Lion City Cup and the Group 3 Paititi Gold Trophy, both over 1,200m, and their eighth in the KrisFlyer.
Said Brown: "He's been good to me. He's one of my first rides when I got to Singapore. Look, he's a good horse and I am really happy for Michael and his connections to actually get a win with me on board.
"He's actually very good. He's getting more and more mature. I said to Michael after his win Monday it wouldn't be a surprise if he gets the mile the way he went.
"He never showed a turn of foot with me over six furlongs (1,200m) but, Monday over seven furlongs (1,400m), he actually attacked the line solid."
Mr Big, whose victories included the RM1 million ($385,000) Malaysian 2012 Magic Millions Classic over 1,200m in Penang last December, has now brought his stakes past the $2m mark with Sunday's win.
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