Three Generation Breeders' Cup Heroines

Three Generation Breeders’ Cup Heroines

 Joseph Di Rienzi

The Breeders’ Cup World Championship series of races dates from 1984. In its history, there have been many bloodline connections among the honor roll of victors. There have been Breeders’ Cup winning horses siring future Breeders’ Cup champions and female Breeders’ Cup heroines producing future winners. However, so far, there has been only one female line that has engendered three generations of distaff victors. The Personal Ensign – My Flag – Storm Flag Flying triumvirate is remarkable not only in its achievement but in that all three females were bred and owned by the Phipps family and trained by Shug McGaughey.

Personal Ensign, the matriarch of this tri-generational bloodline, was one of the greatest distaff runners of the 20^th century. A stately bay by Private Account out of the mare Grecian Banner, she by Hoist the Flag, Personal Ensign was a particular favorite of owner Ogden Phipps. In her only starts as a juvenile in 1986, she won a maiden race at Saratoga Racetrack and then scored a narrow victory in the Frizette Stakes at Belmont Park. In preparing for the Breeders’ Cup Juvenile Fillies, Personal Ensign suffered an injury to her right hind ankle requiring surgery and the insertion of five screws which threatened her racing future. Personal Ensign would return in the fall of 1987. In four starts as a sophomore, she won the Rare Perfume and Beldame Stakes to keep her unbeaten record intact at six for six.

Personal Ensign had a more extensive campaign as a four-year-old in 1988 than in her previous two racing seasons. She came into her final start, the Breeders’ Cup Distaff, still undefeated with victories in the Shuvee, Hempstead, Molly Pitcher and Whitney (against males) Handicaps, as well as the Maskette and Beldame Stakes (this for the second time).

The Breeders’ Cup Distaff run that year at Churchill Downs was one of the most anticipated races of the 1988 Breeders’ Cup. Unbeaten in 12 starts, Personal Ensign would put her streak to a test against Kentucky Derby winner Winning Colors, Kentucky Oaks victor Goodbye Halo, last year’s Breeders’ Cup Juvenile Fillies winner, Epitome, and five others. Personal Ensign was the overwhelming favorite, but the concern in the Phipps stable camp was the condition of the racecourse. Because of her injury two years ago, her connections were adverse to training or racing Personal Ensign on wet surfaces. As the fates would have it, the track on Breeders’ Cup Day was indeed muddy from persistent rain.

The race itself was one of the most dramatic in thoroughbred history and has been replayed endlessly, never ceasing to amaze. As expected, Winning Colors under Gary Stevens bounded to a clear lead followed by Goodbye Halo. Personal Ensign was in mid-pack early and did not seem to be running comfortably over the gooey going. Around the far turn, Winning Colors increased her lead as Goodbye Halo gave chase. Steering his mount to the outside to secure better footing, jockey Randy Romero had Personal Ensign in fourth place some 6 lengths from the lead as the field straightened out for the stretch drive. Goodbye Halo was gaining slowly on Winning Colors, but the Derby winner’s victory seemed likely until Personal Ensign changed leads in mid-stretch and closed dramatically with a will that only true champions can muster. At the finish, Personal Ensign thrust her nose on the line in front of Winning Colors who herself was a ½ length in front of Goodbye Halo. This almost unbelievable ending to a perfect race career guaranteed Personal Ensign honors as Eclipse Champion Older Female. Her performance reminded us all of the courage, class and determination in the best of the thoroughbred breed.

Personal Ensign (on left) winning the 1988 Breeders' Cup Distaff
(bloodhorse.com)

Personal Ensign became a foundational mare in the breeding shed at Claiborne Farm in Paris, KY. She produced major stakes winners Miner’s Mark, Traditionally and My Flag. Personal Ensign also produced stakes placed Our Emblem who was the sire of 2002 Kentucky Derby and Preakness Stakes winner War Emblem. It was My Flag who carried the Breeders’ Cup torch forward. Foaled in 1993, she was the product of two of the best horses to carry the cherry red and black silks of owner Ogden Phipps – Easy Goer and Personal Ensign.

The lanky chestnut, who more resembled her sire than her dam, broke her maiden as a juvenile at first asking at Belmont Park, but she then finished fourth in the Schuylerville and third in a Saratoga allowance race. Stepped up to top competition in the 1 mile Matron Stakes at Belmont Park, My Flag produced a mild rally from last position to finish third to juvenile filly division leader Golden Attraction and her Wayne Lukas trained stablemate Cara Rafaela, beaten a total of 5½ lengths. In the 8½ furlong Frizette Stakes (also at Belmont), Golden Attraction was the strong favorite to continue her domination, and she held sway by ¾ of length over My Flag, who outfitted with blinkers to keep her focused, rallied from last in the five horse field. The diminished margin from the Matron Stakes indicated that the daughter of Easy Goer was improving with racing and would be a threat to her rival in the Breeders’ Cup Juvenile Fillies over the same track and identical 8½ furlong distance.

Breeders’ Cup Day in 1995 had typical late October weather on Long Island, N.Y. Overnight rains and morning showers left the Belmont track carrying a lot of water, but the dirt surface was rated good. The Breeders’ Cup Juvenile Fillies attracted only eight runners, but it had presumptive champion Golden Attraction, and her recent closest pursuers, Cara Rafaela and My Flag. Wayne Lukas also had a third entry in Typically Irish the winner of the Oak Leaf Stakes at Santa Anita Park.

In the early stages of the race, the entry mates occupied the first three positions with Golden Attraction leading Cara Rafaela and Typically Irish. My Flag was out of the gate in last place, but not so far back as in her previous starts. As the field went around the single turn, Typically Irish dropped out of contention and Cara Rafaela came up the rail to challenge her stable mate. Jockey Jerry Bailey had My Flag moving up on the inside drafting behind the two leaders. At the top of the stretch, Golden Attraction looked to be holding off Cara Rafaela, but that changed as the latter forged to the lead mid-stretch. My Flag initially seemed to have too much distance to make up, but, when switched to the outside, she closed dramatically to catch and pass Cara Rafaela in the shadow of the finish for a ½ length victory. Finishing third, 1½ lengths back was Golden Attraction who tired in the closing stages. 

My Flag (in middle) winning the 1995 Breeders' Cup Juvenile Fillies
(photo: bloodhorse.com)

History was made by My Flag’s victory, in that she was the first offspring of a Breeders’ Cup winning dam to have Breeders’ Cup glory. (The story would not be completed on this family legacy as we shall see shortly.) This victory also made up some of the disappointment for My Flag’s sire Easy Goer’s two second place finishes in Breeders’ Cup races.

In 1996 My Flag had a strong three-year-old campaign winning the Bonnie Miss Stakes, Ashland Stakes, Coaching Club American Oaks and Gazelle Handicap. She missed out on garnering a championship when she finished fourth in the Breeder’s Cup Distaff. After a brief winless campaign in 1997 as a four-year-old, she joined her dam Personal Ensign in the broodmare barn at Claiborne. As a producer, My Flag was not as prolific as her predecessor, but she did produce a stakes placed filly in On Parade and a minor stakes winner in With Flying Colors. However, her pièce de résistance was Storm Flag Flying, a 2000 foal by Storm Cat. 

A lithe bay or brown, Strom Flag Flying was owned by Ogden Mills Phipps (son of Ogden Phipps). Making her first start in a 6 furlong race at Saratoga on August 18, 2002, she showed inexperience but rallied strongly from off the pace to win by a length. Shug McGaughey, in an uncharacteristic move for him, next stepped Storm Flag Flying up in class in the 1 mile Matron Stakes in which she destroyed her field winning by nearly 13 lengths. Facing stiffer competition in the 8½ furlong Frizette Stakes in the presence of West Coast invader Santa Catarina, Storm Flag Flying tracked the Bob Baffert trainee most of the race. Taking the lead, under John Velazquez, in the stretch, she was under a hand ride to draw clear by 2 lengths. Santa Catarina was second some 11¼ lengths in front of third finishing Appleby Gardens. An indication of the quality of the performance was that Storm Flag Flying’s final time in the Frizette was faster than the male juveniles ran the identical distance in the Champagne Stakes at Belmont later that same day.

With the Breeders’ Cup races at Arlington Park, just outside of Chicago, IL this year, the juvenile races were lengthened to 9 furlongs due to the configuration of the racetrack. The Juvenile Fillies had a ten horse field headed by the odds-on favorite Storm Flag Flying. Her main competition was presumed to come from the Bob Baffert trained entry of Composure and Santa Catrina. After the start, longshot Humorous Lady opened a clear lead followed by Storm Flag Flying, Santa Catarina and Composure. Nearing the far turn, Santa Catrina went up to challenge the leader temporarily putting Storm Flag Flying between her and Composure on the inside. John Velazquez swung Storm Flag Flying to the outside of Santa Catrina around the stretch turn and forged to the lead. But as she did so, Composure, under Mike Smith, surged three wide and actually gained the advantage over Storm Flag Flying in mid-stretch. But the Phipps filly fought back, as only champions can, and she re-captured the lead. At the finish, she edged clear over Composure by a ½ length with Santa Catrina some 9¾ lengths back. With Storm Flag Flying’s dramatic comeback maintaining her unbeaten record at four for four, she was overwhelmingly voted the Eclipse Two-Year-Old Filly Champion.

Storm Flag Flying winning the 2002 Breeders' Cup Juvenile Fillies
(breederscup.com)

Storm Flag Flying had a futile three-year-old campaign in 2003. After finishing second in the Comely Stakes in April and unplaced in the Acorn Stakes in June, it was revealed she suffered a small fracture of her right cannon bone that prevented her from racing the rest of the year. Storm Flag Flying returned strong as a four-year-old in 2004 winning the Shuvee and Personal Ensign Handicaps and finishing an unlucky second in the Breeders’ Cup Distaff to conclude her racing career. Her death in 2016, brings an end to this Breeders’ Cup legacy as none of Storm Flag Flying’s foals have been good enough to compete in the Breeders’ Cup. 

So this narrative ends with the memories of these three special females who were able to pass on their genetic abilities to their respective offspring and achieve the highest success on three Breeders’ Cup days.