He did something that can often be guaranteed to beat a stayer - he sprinted Rising Romance hard from gate 14 to cross to the rail after 120m.
It nearly won him the race.
Cheekily, on the home turn McDonald sneaked Rising Romance through underneath the leaders and shot clear as rivals were deciding when to make their finishing dashes.
At the 150m, Rising Romance was two lengths clear and looked home and would have been if the only chaser had not been world-class Japanese stayer Admire Rakti.
Japanese stayers are the strongest on the planet and Admire Rakti was relentless, gobbling up the New Zealand mare inside the 75m.
Even in defeat, McDonald showed why his star is heading for the galaxy - he is his own harshest critic.
Like all true champions he is never satisfied.
While everyone else was marvelling at his ride, McDonald was saying quietly: "I went 50m too soon [on the home turn]."
No one else was blaming McDonald, not even Rising Romance's trainer Donna Logan, who declared pre-race that victory would be the greatest moment of her life.
"James rode her beautifully," she said. "He couldn't have done any more." McDonald tried bravely to mask his bitter disappointment. "I thought we were home, I really did."
The sad part for the Rising Romance team is that it is the first time in eight years the Japanese horses have been in Melbourne.
In almost any other year the Rising Romance camp would still be drinking champagne this morning.
The Logans have done a marvellous job with Rising Romance who had her first race 12 months ago almost to the day, finishing fourth in an Avondale maiden.
Some of the team are keen to tackle the A$1 million Mackinnon Stakes at Flemington on Saturday week, but Logan wants to get the mare home for a spell.
"She's an Oaks winner and has done a great job. There's plenty of racing ahead for her, there is no hurry.
"I'd love to take her home right now."
For McDonald the fight goes on. He rode his 1000th winner at Caulfield on Saturday.
He will be in the headlines and one who could help take him there is that 1000th winner, former English stayer Contributor, who made a winning Australian debut in the A$150,000 David Jones Cup.
The High Chaparral stayer was bought by Godolphin from the stable of Ed Dunlop after winning at Ascot in June. McDonald has a high opinion of the 5-year-old. "I rate him better than Fiorente [2013 Melbourne Cup winner]."
If that's accurate the 2015 Melbourne Cup is in the crosshairs.
Meanwhile, the Tomoyuki Umeda-trained Admire Rakti reinforced the strength of Japanese stayers in world racing and his win came eight years after Japanese duo Delta Blues and Pop Rock ran the quinella in the Melbourne Cup.
In claiming one of Australia's best races, Admire Rakti has also stamped himself as having undeniable claims for the Melbourne Cup.
He is the new favourite for Flemington on November 4.
Jockey Zac Purton has climbed to the top of the tree in Hong Kong racing with his first premiership last season and Saturday's win was one of his biggest moments on home soil.
"I thought I was on the right horse for this race," Purton said.
Kerrin McEvoy said third-placed Lucia Valentina was game in defeat after settling back in the field.
"She still hit the line strongly but the winner was just a bit too sharp inside that last furlong and a half."
Melbourne Cup plans remain in place for Lucia Valentina.
So near, yet so far
*Rising Romance looked the Caulfield Cup winner in the home straight.
*Melbourne Cup favourite Admire Rakti proved too strong.
*Win confirmed the class of Japanese-bred stayers.
- additional reporting: AAP
