Banking on his uncanny knack for improving aged horses, Pitman gladly wrote out a cheque for $20,000 for the well-tried El Chico.
He later convinced loyal stable backer, South Island Owner of the Year John Carran and wife Evelyn to buy the horse off him.
But so taken were the Carrans with Pitman's enthusiasm they promptly gifted him a quarter-share.
"I said to John we might have a bit of fun with this horse and what an understatement that's turned out to be," said Pitman.
Yesterday's group three Stewards was the trio's seventh win with El Chico since he won first up for the new owners in October last year.
His biggest victory before now was the group three $70,000 Christchurch Casino Easter Cup (1600m) in April when he more than doubled their investment in one hit.
The Carrans and Pitman were desperately unlucky not to cash in even more during a luckless six-start Queensland campaign last winter.
But Pitman was confident of a decent consolation in the $100,000 Stewards, a race he's now won four times in the past five years.
"We set him for this race and it's very satisfying to have it work out," said Pitman.
"He's such a grouse little horse. He's not a Telegraph or Railway type; just so genuine and honest."
Rider Lisa Allpress was always confident of winning her third straight Stewards once she had bull-dogged her way past Bolinger early in the run home.
"I couldn't even tell you what ran second and third - I was just so focused on getting him up there into a spot he could win from," said Allpress.
"It was pretty devastating losing Coup Align to Singapore. You think how do you replace a horse like that who has been right up there in all the big sprint races?
"But El Chico is just such an honest horse; he's awesome to ride and Michael and the team have done everything right getting his weight right for this."
Pitman said El Chico would back up - "All my horses back-up" - in the $40,000 open sprint at Riccarton on Saturday.
A call to the handicapper last night was to be the deciding factor in My Good Grace's camp keeping the party fires stoked through to the weekend.
Ruakaka co-trainer Donna Logan said the impressive winner of her main Riccarton mission yesterday, the listed Valachi Downs Canterbury Breeders Stakes, may also reappear Saturday if the weight is right.
Before her listed success, My Good Grace had been allotted just 56kg for the R85 1600m, but is unlikely to escape a re-handicap.
Before the 4-year-old's career-high victory - her fifth from just 18 starts - the daughter of Logan's former juvenile star Good Faith had turned in the worst performance of her life.
Logan said that run, an 11th at Ellerslie on October 22, had her owners ready to pull the pin on the raid to Riccarton for the valuable breeding black type.
With a hunch that the mare might just need a sharpen up, however, Logan tried her in a hood for the first time.
"The first time we did that I had the same horse I had when she was a 2-year-old - she worked sensationally," said Logan.
"So I said 'come on, bugger it, we've got to go'."
Logan said the raceday rain didn't help her niggling pre-race doubts that the Ellerslie run masked something more sinister.
But her concerns were dispelled almost from the moment the field jumped and Jason Collett, a late replacement for the injured James McDonald, turned on a copybook display.
"He just sat in behind the speed and waited for the last bite at them - it was a beautifully-timed run," said Logan.