Youngest of Five has been first or second in three of four seven-furlong starts. Overall, he has six wins and $282,100 in earnings from 22 career outings.

What he doesn’t have – yet – despite several sterling efforts, is a stakes win. Youngest of Five has finished second, third, second, and fourth in his last four outings, all in stakes company. Two of those defeats came by a head and a neck, and none was by more than four lengths. Those came after the son of Super Saver had won two consecutive allowance contests.

“He’s had some troubled trips – he really has,” McMahon said of his runner’s stakes outings. “I think a couple of them, he might have prevailed in those races.”

Last time out, in the Not for Love for Maryland-breds, Youngest of Five finished a somewhat disappointing fourth, though beaten less than three lengths, as the 5-2 post time favorite. He was up close early, steadied and dropped back rounding the turn, then found his best stride too late.

“The horse is massive. He’s got a lot of muscle mass,” McMahon said. “Once he’s in gear, you can’t interrupt him. If you kill the momentum, it’s hard for him to regroup and get going again.”

Angel Cruz had ridden Youngest of Five in six straight, including the two allowance wins, and while McMahon doesn’t blame the journeyman for the troubles Youngest of Five has found, he is making a rider switch. Apprentice Jean Alvelo will get the mount, and a chance to earn his first stakes victory.

Though as an apprentice, Alvelo typically can ride with a five-pound weight allowance, in stakes competition that allowance is waived. But McMahon is not troubled by that.

“He’s just been riding so well for us lately,” he said. “He’s got a good head on his shoulders, and I’m not bothered about the weight. He’s one of those kids that listens, and he does his best. I know there are a lot of external variables that influence the outcome, but he tries to do what we ask, and if you lose on your terms, that’s on us.”

The Whiteley is carded as Saturday’s seventh race. Among the rivals Youngest of Five will face are G3 General George show horse Sir Alfred James; American Patrol, making his first start since last June; and Dave’s Friend Stakes winner Threes Over Deuces.

Youngest of Five was bred in Maryland by Sagamore Farm LLC and began his career in Sagamore colors. McMahon claimed him for $50,000 out of his fourth career start, in June 2020. He’s now owned by Larry Rabold.

Rabold also owns the comebacking Excellorator, the 2021 Tesio Stakes runner-up who recently returned from a lengthy break to win a Laurel Park allowance. In the game for more than 20 years, and the owner of nearly 270 wins since 2000, Rabold has just one stakes win to his name, that coming in 2009, according to Equibase.

“He’s so excited,” McMahon said of his owner, and the big season he may be looking at. “He’s a guy that was on the brink of getting out, and this has given him a revival.”

YOUNGEST OF FIVE PHOTOS