Before Oct. 12, it had been over two years since City Boy ran in the only stakes of his 15-race career. The 5-year-old City Zip gelding was the second-longest shot on the board in Saturday's CA$280,900 (US$212,874) Nearctic Stakes (G2T) at Woodbine, but he got up between horses at the wire to pull a 24-1 upset.
"I nominated him, before his last start, to this," said Michael Keogh, who trains City Boy for The Estate of Gustav Schickedanz and Don Howard. "I just thought if no heavy hitters shipped in, it would be worth taking a shot. And that's what happened."
City Boy last visited the winner's circle in an August 2017 allowance race at Woodbine and only started twice the following spring. He returned from an 11-month layoff in April and hit the board in three of four starts entering the Nearctic. In his previous race, he finished third behind grade 3 winner Shakhimat and fellow Nearctic contender Reconfigure in a six-furlong allowance optional claimer on Woodbine's turf.
Back at the same distance in Saturday's turf sprint, City Boy was settled third by jockey Jesse Campbell as last year's runner-up, Yorkton, took the lead from the outside post and set fractions of :22.54 and :45.13 through a half-mile. Richiesinthehouse was in second, two lengths behind Yorkton, a quarter-mile in, and the lead shortened to one length at the half-mile.
Yorkton yielded in the stretch, but Richiesinthehouse and City Boy continued on to his outside. Coming on the far outside was Reconfigure, who ranged up on City Boy's right. It was a three-horse photo finish, but City Boy got his head down between horses to complete six furlongs in 1:08.18 on yielding turf.
Reconfigure held for second over Richiesinthehouse in third. The 2-1 favorite, Blind Ambition, was fourth, and Yorkton faded to sixth.
City Boy was bred in Ontario by Schickendanz, who died June 17. The bay was the last foal out of the Bold Ruckus mare Princess Ruckus, a stakes winner herself at Woodbine. Princess Ruckus produced seven winners, including multiple Woodbine stakes victor Vibank, and is a half sister to multiple grade 1 winner, Canadian champion, and pensioned stallion Langfuhr.
From 16 starts, City Boy has a 3-6-2 record with earnings of US$297,148. Keogh said he had no immediate plans for the gelding's next race.
"It's been a long year. This one … a difficult year," he said. As for the Nearctic win, "It's great. I'm just going to savor the moment. This one's for Gus."