Massimo begins his push for the Group 1 Railway Stakes (1600m) in November under a new training combination at Belmont Park on Saturday.
The Sessions gelding has his first start for Chris and Michael Gangemi in the Listed Black Heart Bart Stakes (1200m).
Massimo won eight races from 24 starts for Adam Durrant with his signature victories the Placid Ark Stakes and Farnley Stakes.
A $736,380 stakes earner, the quality five-year-old was bought by the Gangemi stable for $150,000 in an online auction sale.
Massimo gave the Gangemi’s a glimpse of what could lay ahead in the next couple of months after excelling in a warm-up trial.
Never tested and put under any serious pressure by Clint Johnston-Porter, Massimo was eased down on the line and won easily.
Michael Gangemi is sure Massimo can run a good race first-up for his new stable.
“I’ve been really happy the way he has transitioned into a new environment,” Gangemi told The Races WA.
“He has adapted to our way of working and learning a new system very comfortably.
“He doesn’t have to improve that much from where he has come from.
“Adam (Durrant) did such a great job that we might only need another five or 10 per cent out of him.
“If we could get a return this prep it will be a bonus.
“The Railway Stakes is his grand final and he won’t be fully wound up on Saturday, but I’m confident he will run a competitive race.
“I will be disappointed if he doesn’t figure in the finish.
“He’s a real nice horse and up there with some of our better ones.”
Massimo has been easy with Tabtouch, drifting from $3.20 to $4.40.
Laverrod the big firmer, $3 into $2.40 and favourite. Valour Road is next at $5.50.
Gangemi says the market is close to the mark.
“Laverrod is going to be very hard to beat,” Gangemi said.
“And if Simon (Miller) has Valour Road fully wound up it could be a threat.
“It’s going to be a good race.
“Whatever Massimo does I’m sure he is going to improve.”
Clint Johnston-Porter has chosen to ride Massimo over Mystical View.
He’s been aboard the gelding in four of his eight wins including the Farnley Stakes.
Johnston-Porter will steer Massimo from barrier five.