In what was considered one of the strongest St Leger fields in years, the James Cummings-prepared Alegron became the first Group 1 Penfolds Victoria Derby (2500m) placegetter to take the autumn classic since Khalif completed the Derby-St Leger double in 1966-67.
With rider Damien Oliver sporting the ANZAC Day khaki silks, worn by every topweight at the meeting, Alegron raced clear of the pace-setting The Cunning Fox to score by two and a quarter lengths with filly Fearentless third, four lengths from the winner.
Raging Bull, who finished fourth in the Penfolds Victoria Derby, filled the same spot in the St Leger.
"It is such a time-honoured race and it is a great honour to be able to win the St Leger," Cummings said. "It's quite something to be able to say that Alegron is a St Leger winner so we can enjoy this win today and we're pretty satisfied that we've got a promising stayer going forward.
"He's got a formidable record at 2000m and above and I think he can continue on with it.
He hasn't got a turn of foot so much as he is a wonderful stayer and he's still working out what it is all about, he's still a bit of a baby. As he continues to develop and put those things together, he's got to be a promising stayer."
The win earned Alegron a ballot-exempt spot in The Andrew Ramsden at Flemington's next meeting on May 14, with the Group 1 South Australian Derby (2500m) on the same day also a possibility as Cummings confirmed that the Teofilo gelding would continue his campaign into May.
And while his next port of call remains up in the air, Cummings reinforced his belief that the three-year-old could develop into a Lexus Melbourne Cup contender and would - in time - prove capable of giving the Godolphin operation their second victory in the race that stops the nation.
"We'll talk about it because both races are of the highest quality and are tough," he said. "The imported horses that you come across in an Andrew Ramsden are very solid and so there's that to consider, while the South Australian Derby is a Group 1 race and attracts a strong field.
"We kept him lightly raced early this preparation for a reason and now we are looking to capitalise on that."
It was a third VRC St Leger win for Oliver, who scored a memorable success on Grey Song in 2002 before riding Moment In Time to a dead heat victory with Inkster in 2008.
"He just outstayed them," Oliver said. "He seems to have relaxed even better and he's always indicated that a trip will really suit him."
Oliver's victory took him to 13 Flemington wins for the season, putting him ahead of James McDonald on 12 as well as Jye McNeil, who rode an ANZAC Day treble. Craig Williams and Damian Lane sit on 11 with Jamie Kah on 10.
The last horse to win the VRC St Leger and the Lexus Melbourne Cup in the same year was Gurner's Lane four decades ago, while it is 30 years since the mighty Subzero finished second in the St Leger before going on to win the Cup that same year.
Under the set weights conditions of The Andrew Ramsden, three-year-olds are well-treated, carrying 54kg as opposed to their older rivals who are saddled with 58kg (four-year-olds) and 58.5kg (five-year-olds).
The William Newton VC Handicap (2600m), which opened the ANZAC Day meeting, also offered a ballot-exempt spot in The Andrew Ramsden if the winner was aged four or five.
The opener was taken by 2019 Ramsden winner Steel Prince, who will not line up in the Ramsden this year due to the conditions of the race.
However, runner-up English King - who started second favourite in the 2020 Epsom Derby before finishing fifth - produced his best run in Australia to date and will head to the race for Flemington trainer Mike Moroney.
Other horses pointing towards The Andrew Ramsden include last year's VRC St Leger winner Through Irish Eyes, promising import Luncies, runaway Saturday victor Grandslam and his stablemate Maserartie Bay.
Adelaide Cup winner Daqiansweet Junior also remains a possibility.
The day's other feature, the Listed ANZAC Day Stakes (1400m), saw the Ben and JD Hayes-trained Tijuana follow in the footsteps of Group 1 winners Merchant Navy and Long John in taking the two-year-old contest.
