On Monday morning at trackwork, Gray was just sharing with Vlad Duric that the brilliant son of Per Incanto was still riderless in this Saturday's $300,000 Group 1 Lion City Cup (1200m), given regular partner Simon Kok Wei Hoong had opted for Fame Star.
Duric could have been an eligible candidate himself given his regular assistance with the four-time winner's gallops and barrier trials, and more pointedly, he likes the horse, but the four-time Singapore champion jockey was already committed to James Peters' Grand Koonta.
That was when the Australian hoop selflessly suggested Oscar Chavez.
As fate would have the Panamanian-born jockey and MRA (Malayan Racing Association) veteran just happened to be walking up one of the shrub-lined paths at Kranji at the very same time.
Like manna from heaven, the timely deal was closed in a jiffy, but killing two birds with one stone, it was also the perfect opportunity for Gray to square Chavez off with an overdue restitution.
"I didn't have a rider for Sure Will The young apprentice Hakim (Kamaruddin) was free, but at weight-for-age, I preferred a senior jockey," said Gray.
"On Monday, Vlad told me he would have gladly ridden him if he wasn't riding James' grey horse, and that's when he said 'what about Oscar?'.
"As I turned around, guess who's there, Oscar himself. There's no more talented horseman than Oscar Chavez, I knew right away Sure Will Do would be in good hands.
"Oscar will not rush him, especially as he's drawn out (12), he'll look after him, he'll ride him patient. He's the right guy for this.
"But there was also something else I was thinking of when I booked him. Oscar was down to ride Lim's Prestige in the (Group 1 Emirates Singapore) Derby back in 2007, but he was stood down after he got crook.
"Din Azis took the ride and we know the rest, Lim's Prestige won, poor Oscar. It was time to give Oscar another chance to ride in a Group 1 race for me – but wait, the horse has to win first, and then that'll be the story!"
Chavez, who just returned from a thumb injury that sidelined him for two months, not to mention an even longer time twiddling his thumbs for non-renewal of licence – three years (2018-2020) - is certainly hopeful Sure Will Do can live up to his name and tie up those loose ends with a happy ending.
A winner at his second meeting back with Sun Ops last Sunday, the 46-year-old Latino, who is now a naturalised Singaporean, has somewhat got over the Lim's Prestige shortfall.
He actually had already won a Singapore Derby in 1994 aboard Noble Spirits for ex-Kranji trainer Mohd Yusof, but if there was any sting left to the agonising miss 13 years later, Gray's attempt at redemption has brought up the lighter side of it.
"Don't remind me of that Derby that got away!" said Chavez in mock indignation.
"Steve asked me if I forgot how to win Group 1s after that. I told him don't worry, maybe I haven't won a Group 1 race since, but I sure have won a few Group races (like the 2015 Group 2 EW Barker Trophy on Gold Rutile and the 2016 Group 3 Singapore Three-Year-Old Sprint on Conflight, his last 'black-type' win).
"Even if I have never ridden Sure Will Do in a race or in trackwork, I've done my homework and watched all his races, don't worry about that.
"I spoke to Steve today, he was a bit concerned if the horse could measure up at that level at weight-for-age, but I told him not to worry. His horse is an up-and-coming four-year-old and has plenty of upsides.
"He was worried about the barrier, but I told him there was only one way to ride him. If he goes with the speed from that barrier, you will slaughter him.
"The only way is to jump him out, and wait for him to come back by himself as I think there will be a lot of pace in the race.
"Steve was on the same page as Hopefully, we can sit midfield, and I'll just have to ride him for luck."
Among his 1,200-odd wins, Chavez boasts one Lion City Cup win to a decorated riding career that began in Panama before moving to the MRA circuit in 1993 – Golden Glory for Yusof again in 1996.
It was run in the second-slowest time in the premier sprint's 47-year-long history: 1min 15.3secs, just under one second quicker than Fischer's 1min 16.2secs three years later.
"I remember that race. We won on a very heavy track," said Chavez whose last Group 1 success came in the Kranji Mile aboard the John Meagher-trained Recast in 2006.
Besides Sure Will Gray has also engaged Kharisma in the Lion City Cup, which will be the first Group event to be run at Kranji this season. Unlike Sure Will a jockey was secured rather quickly for the four-year-old son of Mossman.
"CC (Chin Chuen) Wong won on him at his last start, but CC is on Rocket Star," said Gray.
"The horse won well for Troy See before. He put his hand up and I was happy to put him back Troy's a good jockey.
"Both horses have drawn wide (Kharisma jumps from gate No but they're both good horses in good hands."