A 9-year-old gelding, Cloudy’s Knight won for the second time in as many starts this season and notched the fifth graded stakes victory of his remarkable 38-start career. The son of Lord Avie, a homebred of Jerrold and Shirley Schwartz’s S J Stables, has earned more than $2.2 million. He is trained by Jonathan Sheppard.

Cloudy’s Knight, ridden by Rosemary Homeister Jr., was in no hurry during the early stages of the 1 1/2-mile Sycamore while longshot Rumor Has It rolled to a big lead. Timeless Fashion, Americain, Free Fighter, and Caberneigh all chased the early leader through splits of: :24.16 and :48.19.

When they made their made onto the backstretch, Timeless Fashion and Free Fighter (one-mile in 1:41.45) each made strong moves to the front, while American and Gentleman Chester also made their way near the front approaching the final turn. But Yate's Black Cat, under the handling of Miguel Mena, was the biggest threat as they continued to the quarter-pole and he came off the turn with the lead.

Timeless Fashion and Free Fighter chased Yate’s Black Cat into the stretch as he opened up a half-length lead at the eighth-pole and extended his advantage by mid-stetch. But just when it looked as though the 6-year-old son of Black Minnaloushe was home free, Cloudy’s Knight and Winchester came roaring down the stretch while splitting horses together. Just a few yards from the wire, the duo caught Yate’s Black Cat, with Cloudy’s Knight hitting the wire a head in front of Winshester and Ramon Dominguez.

The final time for 12 furlongs on the firm turf course was 2:30.87. Yate’s Black Cat was a half-length back in third.

"At the eighth-pole, I thought I might be second or third," Homeister said. "When (Winchester) headed him, he just took off with him. He's very game, aggressive, and he handled the turf course perfectly."

Cloudy’s Knight, recovering from a hind leg tendon injury at the beginning of 2009, made his season debut Sept. 19 in the Kentucky Cup Turf (gr. IIIT) at Turfway Park after a more than one year layoff. The veteran won by 2 1/2 lengths to set up his run in the Sycamore.

Bred in Kentucky and out of the Solar City mare Cloudy Spot, Cloudy’s Knight produced his best season in 2007 when he won the Sky Classic (Can-IIT) and Pattison Canadian International (Can-IT) at Woodbine en route to being named Canada’s champion grass horse. Overall, he has now won 12 times for earnings of $2,255,626.

"He's quite something," Sheppard said. "He's an amazing animal, he really is. He's got a great stride and Rosemary seems to have a great rapport with him. All of this came together at the right time."

Sent off as the second choice, Cloudy’s Knight paid $10.20, $4.80, and $4.20. The exacta (9-12) returned $33 and the trifecta (9-12-8) was $361.60.