Making Money Betting the Synthetic Surface Specialists in Turfway's Jeff Ruby Steaks
As the Road to the Breeders' Cup series picks up momentum this month, the focus for upcoming weekend shifts to Woodbine in Toronto, which will host three “Win and You’re In” Challenge Series races on Saturday, Sept. 17.
Saturday’s slate at the Toronto, Ontario track is highlighted by the Ricoh Woodbine Mile Stakes, a “Win and You’re In” qualifier for the FanDuel Breeders’ Cup Mile Nov. 5 at Keeneland. Earlier on the card are the Natalma Stakes and the Pattison Summer Stakes. These are Challenge Series “Win and You’re In” races for the Breeders’ Cup Juvenile Fillies Turf and the Breeders’ Cup Juvenile Turf on Nov. 4, respectively.
A handful of other races scheduled for the weekend, while not “Win and You’re In” races, have been influential on the World Championships in years past, particularly the Iroquois Stakes and Pocahontas Stakes for 2-year-olds at Churchill Downs. Both of those races were removed from the Challenge Series for 2022.
The 14 Breeders’ Cup races attract the best Thoroughbreds in the world to compete for more than $31 million in purse money and awards, and the selection of starters in each race is determined in part by a points system for graded stakes and the selection criteria of a panel of experts. However, there is one way for an owner to bypass the secondary criteria and secure a spot for their horse in a Breeders’ Cup race, and that is by winning a stakes race in the Breeders’ Cup Challenge Series.
Here’s some background on this weekend’s “Win and You’re In” qualifying races and other races that have made an impact on the Breeders’ Cup.
The Ricoh Woodbine Mile has a rich history since its first running in 1997, and the crossover between this signature race north of the border and the Breeders’ Cup Mile began immediately. Inaugural Woodbine Mile winner Geri shipped to Hollywood Park for the Breeders’ Cup Mile and finished second behind European invader Spinning World for owner Allen Paulson and trainer Bill Mott of Cigar fame. In 1998, Woodbine Mile winner Labeeb was third in the Breeders’ Cup Mile and, over the next several years, Woodbine Mile winners continued to make good showings in the Breeders’ Cup Mile on occasion, including Good Journey (third in 2002), Touch of the Blues (second to Six Perfections in 2003), and champion Leroidesanimaux (second to Artie Schiller in 2005). In addition to those horses, 1999 Woodbine Mile fifth-place finisher Silic won the Breeders' Cup Mile two starts later by a neck over Tuzla. The Woodbine Mile was run as the Atto Mile from 1999 to 2005.
In 2007, fan favorite and Oklahoma-bred Kip Deville was in the midst of a breakthrough season when he finished second by a length in the Woodbine Mile to Shakespeare. He subsequently unleashed a career-best performance in his next start, powering through the stretch of Monmouth Park’s rain-softened turf course to take the Breeders’ Cup Mile under Cornelio Velasquez. Kip Deville would continue his good form into 2008, and finish second behind Hall of Famer Goldikova in that autumn’s Breeders’ Cup Mile.
Juddmonte Farms' Ventura, trained by Hall of Famer Bobby Frankel, won the Woodbine Mile in 2009, a year after taking the Breeders' Cup Filly and Mare Sprint on Santa Anita Park's synthetic main track. Durable Court Vision made three consecutive starts in the Breeders’ Cup Mile from 2009 through 2011, and also appeared in two editions of the Woodbine Mile. The son of Gulch won the Woodbine Mile in 2010 but finished seventh in 2011 to Turallure. He had finished fourth and fifth, respectively, in his prior Breeders’ Cup Mile efforts and was sent off at odds of 64.80-1 at Churchill Downs in 2011, coming out of that seventh-place showing at Woodbine and squaring off against heavy favorite Goldikova, who was aiming for her fourth consecutive Breeders’ Cup Mile win. What commenced was one of the most exciting races in Breeders’ Cup history and a monumental upset win for Court Vision, who edged Turallure by a nearly imperceptible nose, with Goldikova a vanquished third. Court Vision had changed owners and trainers through the years and was by fall 2011 owned by B. Wayne Hughes’ Spendthrift Farm and conditioned by Dale Romans. The Breeders’ Cup Mile was his final career start.
The Woodbine Mile-Breeders’ Cup Mile symbiosis has continued to be strong in recent years, thanks to champions Wise Dan and Tepin. Wise Dan received Horse of the Year honors in 2012 and 2013, and among the races he won during that timespan were consecutive runnings of the Woodbine Mile and the Breeders’ Cup Mile. In both 2012 and 2013, Charles LoPresti used the Woodbine Mile and the Shadwell Turf Mile at Keeneland as preps for Wise Dan heading into the Breeders’ Cup. The gelding’s only blemish among those six races came in the 2013 Shadwell Turf Mile when it was rained off of the turf and he finished second. All in all, it was an incredible extended streak of excellence by a horse that few will ever forget.
Trade Storm, winner of the 2014 Woodbine Mile, finished third in the Breeders’ Cup Mile as longshots took all top four positions, and Woodbine Mile third-place finisher Bobby's Kitten shortened up in distance and won the Breeders' Cup Turf Sprint with a memorable wide rally through Santa Anita's downhill turf course. A year later, Mondialiste won the Ricoh Woodbine Mile in his first start in North America. He then put forth a valiant effort in his next start, the Breeders’ Cup Mile at Keeneland, that was still 2 ¼ lengths too late to catch dominant winner Tepin. Tepin’s Breeders’ Cup Mile win was the second of what would become nine consecutive victories stretching into fall 2016, ending with a gritty half-length score in the Ricoh Woodbine Mile. She finished second in her final two starts, the last to Tourist in the Breeders’ Cup Mile, before retiring as a two-time champion. Tepin was inducted into the Racing Hall of Fame last month.
The 2017 renewal of the Ricoh Woodbine Mile added to the race’s luster as an important Breeders’ Cup prep. World Approval entered the race off of a visually impressive score in the Fourstardave Handicap at Saratoga, and then made it back-to-back Grade 1 wins, taking the Woodbine Mile north of the border by 2 ½ lengths. Shipped to Del Mar for the Breeders’ Cup Mile, the striking gray gelding collected his third top-level win in a row for owner Live Oak Plantation and trainer Mark Casse (who trained Tepin). Lancaster Bomber, runner-up in the 2016 Breeders' Cup Juvenile Turf, completed the exacta in both the 2017 Ricoh Woodbine Mile and the Breeders' Cup Mile. Based on his stellar late-season run, World Approval was awarded champion turf male honors for 2017.
In 2019, Got Stormy was sent off as the 1.55-1 favorite in the Woodbine Mile coming off of a Saratoga meet where she won two stakes races in one week’s time. The Mark Casse-trained filly was second best to 44.70-1 local horse El Tormenta, who rallied past her late to win by a half-length. Got Stormy followed up that showing with another runner-up effort against Uni in the Breeders’ Cup Mile at Santa Anita (El Tormenta finished sixth). Got Stormy raced for two more years and finished fifth in the 2020 Breeders’ Cup Turf Sprint and fifth in last year’s FanDuel Mile Presented by PDJF, her last race before being retired. Grade 1 winner Raging Bull, third in the 2021 Ricoh Woodbine Mile, was subsequently fourth ahead of Got Stormy in the final career start for both at Del Mar.
Since the Breeders’ Cup Juvenile Fillies Turf was first held in 2008, the one-mile Natalma Stakes has sent several elite fillies on to the World Championships; however, in the first few years when both races were run, it was the also-rans who had more of an impact. In 2010, More Than Real brought famed chef Bobby Flay to the Breeders’ Cup winner’s circle after scoring a 13.60-1 upset in the Juvenile Fillies Turf at Churchill Downs; the More Than Ready filly had finished second in the Natalma one race before.
The next year, Ken and Sarah Ramsey’s Stephanie’s Kitten finished third in the Natalma but then won the Grade 1 Darley Alcibiades Stakes at Keeneland on the synthetic main track and followed that with a driving three-quarter-length win in the Juvenile Fillies Turf, again at Churchill Downs. Stephanie’s Kitten would go on to finish second in the 2014 Breeders’ Cup Filly and Mare Turf and then win that same race in her final start a year later. She earned nearly $4.3 million in a probable Hall of Fame career. (Incidentally, 2011 Natalma runner-up Dayatthespa would become an elite turf filly in her own right, just on a slower timetable. She bested Stephanie’s Kitten in the 2014 Filly and Mare Turf and won the Eclipse Award in her division that year.)
More recently, Catch a Glimpse became the first filly to win both the Natalma and the Juvenile Fillies Turf when she did so in 2015. Her three-quarter-length win in the latter race at Keeneland was one of two victories for Mark Casse during the two-day Breeders’ Cup, the other coming with the aforementioned Tepin in the Mile.
Last year’s Natalma winner, Wild Beauty, shipped in from England and dominated the race at Woodbine by 2 ¼ lengths over Pizza Bianca for owner Godolphin and trainer Charles Appleby. Wild Beauty went right back to the U.K., however, and did not return for the Breeders’ Cup at Del Mar. Pizza Bianca, on the other hand, did contest the Juvenile Fillies and was sent off as the 9.90-1 sixth betting choice in a wide-open race. Last of 14 after six furlongs, the Fastnet Rock filly weaved through traffic in the stretch under adroit handling by Jose Ortiz to get up and win by a half-length, giving Bobby Flay his second Juvenile Fillies victory following More Than Real in 2008. It was also the first win in the World Championships for renowned trainer Christophe Clement, ending an 0-for-40 streak.
The one-mile Summer Stakes on Woodbine’s turf made an impact on the Breeders’ Cup the year before the Juvenile Turf was inaugurated, which was in 2007 at Monmouth Park. In 2006, the Wayne Catalano-trained filly Dreaming of Anna raced against males and won the Summer Stakes by an easy 3 ¼ lengths one race prior to scoring a similarly impressive 1 ¼-length win in the Breeders’ Cup Juvenile Fillies on dirt at Churchill Downs.
Two years after the Juvenile Turf began, 2009 Summer Stakes winner Bridgetown set the pace in the Breeders’ Cup event at Santa Anita and held on strongly to finish a very good second to European shipper Pounced. And one year later, Pluck became the first horse to win both races, scoring by a length in the Summer Stakes and then rallying from last under Garrett Gomez to win the Juvenile Turf by the same margin at Churchill Downs for Team Valor International.
In 2011, Excaper finished second in both the Summer Stakes and Juvenile Turf, and in 2014 and 2015, Summer Stakes winners Conquest Typhoon and Conquest Daddyo – both owned by Conquest Stables and trained by Mark Casse – each finished fourth in subsequent editions of the Juvenile Turf. In 2016, Good Samaritan won the Summer Stakes by 1 ½ lengths and then ran a good third behind Oscar Performance and Lancaster Bomber in the Juvenile Turf at Santa Anita. He trained on to be a solid turf performer as a 3-year-old and also showed his versatility by switching to dirt and winning the 2017 Grade 2 Jim Dandy Stakes Presented by NYRA Bets. Later in 2017, Graham Motion-trained Untamed Domain captured the Summer Stakes by a neck and then backed that up with a late-rallying second to Mendelssohn in the Breeders’ Cup Juvenile Turf at Del Mar.
In 2018, War of Will finished second to Fog of War in the Summer Stakes and would train on to finish a good fifth in the Breeders’ Cup Juvenile Turf. Switched to dirt, he become a classic winner at age 3 when taking the 2019 Preakness Stakes.
Other weekend races:
The Iroquois Stakes and Pocahontas Stakes are the first qualifying points races for the 2023 Kentucky Derby Presented by Woodford Reserve and the 2023 Longines Kentucky Oaks, respectively. They were Challenge Series qualifiers for the TVG Breeders’ Cup Juvenile and NetJets Breeders’ Cup Juvenile Fillies in years past, but were removed in 2022 as the Breeders’ Cup revised their “Win and You’re In” schedule to conform to a regional format.
Until 2013, both the Iroquois and Pocahontas Stakes were run during Churchill Downs’ November meet and after the Breeders’ Cup, as Turfway Park held the commonwealth’s September dates. In the years since Churchill has moved both races to its abbreviated September meet, no Iroquois winner has gone on to win the Juvenile, although Not This Time came oh so close in 2016. The Dale Romans-trained colt, owned by Albaugh Family Stable, romped in the Iroquois by 8 ¾ lengths, and was sent off as the 2.80-1 favorite in the Juvenile. He dueled with fellow Kentucky-based colt Classic Empire through the Santa Anita stretch but came up a neck short. Unfortunately, Not This Time was retired soon afterward with an injury; he has become one of the most successful young sires in North America, responsible for such notables as leading 3-year-old Epicenter.
Of note: The winner of the 2007 Iroquois was none other than Court Vision, discussed above, who found his true calling on turf later in his career.
Top-class Untapable won the 2013 Pocahontas Stakes, the first edition run in September, but endured a rough trip and was eased in the 14 Hands Winery Breeders’ Cup Juvenile Fillies. By the end of the next calendar year, the Winchell Thoroughbreds-owned filly was 3-year-old champion female and winner of the Longines Breeders’ Cup Distaff.
The 2014 Pocahontas was won by Cristina’s Journey, with 3-2 favorite Take Charge Brandi tiring late to finish fifth. Take Charge Brandi then performed even worse in the Darley Alcibiades Stakes at Keeneland, finishing eighth, but in her next start she scored a 61.70-1 front-running upset in the Juvenile Fillies at Santa Anita. That improbable win, followed by two more stakes wins to close out 2014, was good enough to earn her the Eclipse Award as champion 2-year-old filly.
In 2015, Pocahontas winner Dothraki Queen finished third behind the sensational Songbird in the Juvenile Fillies; and in 2016, Pocahontas winner Daddys Lil Darling checked in fourth behind longshot Juvenile Fillies victress Champagne Room. Four years ago, Serengeti Empress dominated the 2018 Pocahontas to emerge as one of the top fillies of her age group; she disappointed in her next race at Churchill when seventh in the Juvenile Fillies but came back in 2019 to win the Longines Kentucky Oaks and run third in that fall's Longines Distaff. Serengeti Empress closed out her career with a runner-up finish to Gamine in the 2020 Breeders’ Cup Filly and Mare Sprint.
Girl Daddy, winner of the 2020 Pocahontas, ran third behind Vequist and Dayoutoftheoffice in the Juvenile Fillies at Keeneland, and last year’s Pocahontas winner, Hidden Connection, finished fourth behind champion Echo Zulu in the Juvenile Fillies at Del Mar.
The Locust Grove Stakes at Churchill Downs was held on turf until 2012. Since 2013, it’s been carded at 1 1/16 miles on dirt, with 2014 winner Don’t Tell Sophia going on to finish second behind Untapable in the Longines Breeders’ Cup Distaff. In 2018, Blue Prize held on to win the Locust Grove by a nose during a stellar fall campaign that saw her win the Grade 1 Juddmonte Spinster Stakes at Keeneland in her next start and then finish fourth in the Distaff back at Churchill. The Ignacio Correas-trained Argentinian-bred mare would then return in 2019 to capture the Longines Distaff at Santa Anita before heading to the Fasig-Tipton sales ring, where she sold for $5 million as a broodmare prospect.
Lastly, the Caesars Jockey Club Derby Invitational Stakes was made a Grade 3 for 2022. A year ago, it was a listed stakes but nevertheless was included in the “Win and You’re In” Challenge Series as a qualifier for the 2021 Longines Breeders’ Cup Turf. Yibir, a Dubawi gelding owned by Godolphin and trained by Charlie Appleby, shipped to Belmont Park off of a win in a Group 2 stakes at York and made quick work of six opponents in the 1 ½-mile Jockey Club Derby, winning by 2 ½ lengths. Appleby pointed Yibir to a stellar renewal of the Longines Turf at Del Mar, headlined by 2020 winner Tarnawa. With William Buick riding, Yibir rallied furiously from well back to win by a half-length, the last of an incredible three wins in the two-day World Championships for the owner-jockey-trainer combo. This year, the Jockey Club Derby will be held at Aqueduct while Belmont Park undergoes construction and it is not a Challenge Series race.