For those who believe the dead can affect the living, the story of Sippican Harbor is compelling. For disbelievers, the improbable rise of the daughter of Orb bound for the Tito's Handmade Vodka Breeders’ Cup Juvenile Fillies still provides reason to pause.
New York-based trainer Gary Contessa would like to think the late David Cassidy, the former actor and pop artist who became a close friend, is looking out for only the second Grade 1 winner of his career. There is no doubting that everything has gone Sippican Harbor’s way since she ran a troubled fifth when she debuted at a mile and a sixteenth on the turf on July 22 at Saratoga Race Course.
Contessa attempted to wheel her back on the grass at the same distance on Aug. 22. Nature had other ideas. When rain prompted a switch to dirt, Sippican Harbor responded by demolishing her field by 17 lengths.
“It was just meant to be,” said Contessa, 61. “It steered me in the right direction. Just by Mother Nature, we were decreed a dirt horse.”
That eye-opening performance led Contessa to take a shot in the Spinaway, a Grade 1 acid test at seven furlongs on Sept. 1 at Saratoga. In responding to the wishes of Cassidy, an avid breeder and owner, Contessa watched that morning as his friend’s ashes were scattered at the training track at Saratoga.
When the trainer observed that Sippican Harbor faced long odds minutes before the Spinaway, he sought otherworldly intervention. “I looked up at the sky and said, ‘David, if you could help me here, I’d really appreciate it.’ Bingo, she wins.”
Joel Rosario sat chilly at the back of the pack before calling on his mount for her run. She responded with a tremendous rally and defeated Restless Rider by two lengths, delivering at 16-1. The outcome was all the more impressive because Restless Rider, trained by Kenny McPeek, rebounded to win the Grade 1 Alcibiades Stakes last Friday at Keeneland Race Course.
Contessa recorded his only other Grade 1 victory when Do It With Style secured the Ashland Stakes with style in 1991. Do It With Style resented a whip, so Contessa instructed jockey Shane Sellers not to carry one into the Ashland.
“You sure no whip?” Sellers asked incredulously.
“I know my horse,” Contessa replied.
The unorthodox approach was rewarded with a neck victory.
Contessa is looking to send his fourth starter into the Breeders’ Cup World Championships. His first three were sent off as impossible longshots – and they ran that way.
“I’ve always been kind of a blue-collar guy. I go to the sale to spend $50,000 on a horse, not $600,000,” he said. “I’ve never had deep pockets. I have to do what I can do.”
Contessa, who began playing bass guitar as a teenager, and Cassidy were drawn to each other the first time they met. “He was a rock star who wanted to be a horse trainer,” Contessa said, “and I was a horse trainer who wanted to be a rock star.”
Contessa played primarily with club bands. One of his claims to fame as a musician? His band played at the 50th wedding anniversary of mobster Carlo Gambino. Guests were eyeballed at the door by a man with a shotgun.
Cassidy would often invite Contessa to play bass guitar during his concerts. Otherwise, they were united by their passion for Thoroughbreds, not music.
“We always talked about horses,” the trainer said. “You never met a guy as studious on the breeding side as David. He would tell me things that had my head spinning. He was a tremendous student of the game.”
Racing provided an escape for Cassidy, who had a series of issues related to abuse of alcohol. Over the years, Contessa learned to be a good listener when his friend needed to talk, even when those calls came in the middle of the night. Cassidy died on Nov. 21, 2017 of liver failure. He was 67.
Contessa knows Sippican Harbor, owned by Lee Pokoik, is the kind of filly Cassidy would have loved. The greater the distance, the more she relishes it. The versatile youngster already owns victories on the front end and from far back.
Contessa could not be more optimistic as he looks ahead to Nov. 2 at Churchill Downs.
“God willing we get there, I’m going to win the damn thing,” he said. “I love the position I’m in.”
Cassidy would have loved it, too.