It is a shade over four years since the Al Shaqab Racing-owned gelding came within a nose of an historic victory in the Breeders' Cup Classic, and his subsequent travails have been well-documented.
However, he made a Lazarus-like return from a three-year absence when claiming a fairytale success in this race a year ago - and while the Pegasus World Cup on his next start proved too ambitious, he has since run two sound races at Graded level in America to suggest he is no back number.
After finishing a creditable fourth in the Marathon on Breeders' Cup night on his latest outing, Toast Of New York drops in distance and class in the Betway Casino Conditions Stakes - and Osborne is hoping his stable star can make the most of having his sights lowered.
"We had our hand forced a little bit in America, because Toast Of New York only made the reserve list for the Breeders' Cup Classic and so we had to run him over a trip too far in the Marathon," said the Lambourn-based trainer.
"I felt that he ran very well - and even though he didn't get the trip, what it did show is that he is in great heart.
"We brought him back with the view that we are going to lower his sights and give him a winter campaign in the UK.
"I think the race on Wednesday is a nice starting point for him - and provided all goes well, he could end up in the Betway Quebec Stakes back at Lingfield on December 22 before moving onto the Betway Winter Derby and then hopefully All-Weather Championships Finals Day.
"I feel these races at his age are realistic targets. He is probably not the force he once was, but he is still a force - and his rating of 110 puts him bang there."
Toast Of New York faces five rivals in this £19,000 contest.
The other declared runners are Dragon Mall (Rebecca Menzies), Goring (Eve Johnson Houghton), Scarlet Dragon (Alan King), North Face (Marco Botti) and Mango Tango (Archie Watson).
