Mating Plans, Presented By Spendthrift: Chip Montgomery And Haymarket Farm

The TDN's popular annual series 'Mating Plans, presented by Spendthrift,' continues today in a conversation with Haymarket Farm's Chip Montgomery.

“I've always been enamored with the deep pedigrees of the stalwarts of the industry and have gravitated recently to granddaughters, etc. of Personal Ensign, My Flag and Storm Flag Flying,” said Montgomery. “About once a quarter, I will put on the video of the 1988 Breeders' Cup Distaff to hear Tom Durkin's call of Personal Ensign's nose win against Winning Colors to retire undefeated.   It's an honor to own several fillies and mares with this royal blood in their veins, and makes me proud to be a Kentuckian!”

BLESSING THE FLAG, 6, (Distorted Humor–Fly the Flag, by Giant's Causeway). To be bred to Medaglia d'Oro.

We bought her as a yearling and made $130,000 but couldn't win a race!  As a maiden, we will breed her to Medaglia d'Oro as this cross works very well, not only in the population in general, but also within her family (Vigilantes Way and Major Dude, among others).

FLY THE FLAG, 17, (Giant's Causeway–My Flag, by Easy Goer). To be bred to Upstart or Annapolis.

Honoring our investment in stallion shares here as she's in foal to Upstart (bred like Zandon and Trademark) and will likely go back to Upstart or possibly Annapolis.

STAND FOR THE FLAG, 8, (Super Saver–Raise the Flag, by Awesome Again). To be bred to Proxy.

A winner of $290,000, we bought her as a broodmare prospect and she is in foal to Olympiad and going to Proxy. Both good crosses and beautiful animals!

WYCHWOOD, 8, (Tale of the Cat–Queens Wood, by Tiznow). To be bred to Street Sense.

A daughter of a GI-producing mare, she has already produced our homebred stakes winner Cats inthe Timber (Honor Code) as her first foal. Barren this year, she will be bred to Street Sense, needing that size and two-turn power.

QUEENS WOOD, 16, (Tiznow–Salon Prive, by Private Account). To be bred to Forte.

The queen herself, currently in foal to Jackie's Warrior, will be bred to Forte, a proper cross and a powerful two-turn hopeful.

CTIMENE, 15, (Consolidator–Persimmon Hill, by Conquistador Cielo). To be bred to Mitole.

A half-sister to GI producer Once Around, she had a breakthrough stakes winner this past year with Katonah (Klimt) and is being bred to Mitole. A big, course mare, she will benefit from Mitole's sprinter physique.

GOOD TOHAVE AROUND, 4, (Good Samaritan–Ctimene, by Consolidator). To be bred to Yaupon.

A more elegant rendition of her mother, as a maiden, will be bred to the magnificent looking Yaupon.

Interested in sharing your own mating plans? Email garyking@thetdn.com.

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Background Check: Personal Ensign

In this continuing series, we examine the past winners of significant filly/mare races by the lasting influence they've had on the breed. Up today is Saratoga's GI Personal Ensign S., renamed in 1998 to honor the undefeated Hall of Fame Phipps mare.

Originally known as the Firenze H. and then the John A. Morris H., the Personal Ensign dates to 1948. While members of the Phipps family have won six editions of the race which now holds one of the greatest names associated with the stable, Personal Ensign never actually ran in the contest.

In 1987, when the great mare was three, she had not yet returned to the races from a broken pastern bone in her left rear leg sustained as a juvenile. That year's race was run on Aug. 30; Personal Ensign would not come back until a week later in a Belmont allowance, her first start in nearly 11 months. The race would also miss the champion's dance card in 1988, but for a very different reason. She was fresh off a win over males in the GI Whitney S. just three weeks prior.

The transcendent mare's champion granddaughter, Storm Flag Flying (Storm Cat), did win the Personal Ensign S. in 2004. Like her legendary granddam, she was a Phipps homebred raised at Claiborne Farm and trained by Shug McGaughey.

Not only was Personal Ensign an unblemished champion on the racetrack, she also was named Broodmare of the Year in 1996. She produced one champion, three Grade I winners, and a dynasty through her daughters that is still churning out major winners today, including 2023's GISW Arabian Lion (Justify), who is set to run in Saturday's GI H. Allen Jerkens Memorial S., and GSW Major Dude (Bolt d'Oro).

Following are highlights of some of the most important Personal Ensign winners by what impact they've had on the sport through their sons and daughters.

Cavorting (2012, Bernardini–Promenade Girl, by Carson City), bred by Swettenham Stud: A mare this young with two stakes winners to her name wouldn't normally make a list of matriarchs, but one of her foals is Clairiere (Curlin), a four-time GISW and 5-2 morning-line second choice in this year's Personal Ensign.

Heavenly Prize (1991, Seeking the Gold–Oh What a Dance, by Nijinsky II), bred by Ogden Phipps: This Phipps homebred and Hall of Famer produced MGISW Good Reward (Storm Cat), as well as GSW and good sire Pure Prize (Storm Cat). Her descendants include GISW Persistently (Smoke Glacken), a 2010 Personal Ensign winner for Phipps Stable, as well as more recent GISWs Instilled Regard (Arch) and Queen Goddess (Empire Maker).

Number (1979, Nijinsky II–Special, by Forli {Arg}), bred by Claiborne Farm: Japanese champion and MG1SW Gold Dream (Jpn) (Gold Allure {Jpn}), Breeders' Cup and GI Met Mile winner Corinthian (Pulpit), French G1 winner and Japanese sire Jade Robbery (Mr. Prospector), and a 'number' of other graded performers trace to this incredibly well-bred mare from one of the most 'special' families in the stud book.

Relaxing (1976, Buckpasser–Marking Time, by To Market), bred by Ogden Phipps: How fitting that this mare's greatest son would be bred to Personal Ensign, resulting in that mare's greatest daughter, My Flag. This 1989 Broodmare of the Year produced champion and Classic winner Easy Goer (Alydar), as well as GI winners Cadillacing (Alydar) and Easy Now (Danzig). Her descendants include GISW Strolling Along (Danzig), MGSW Cat Cay (Pleasant Colony), and MGSW & MGISP Abaco (Giant's Causeway).

1980 winner Relaxing's son Easy Goer was the sire of Breeders' Cup winner My Flag (outside), a filly out of Personal Ensign who would produce 2004 Personal Ensign winner Storm Flag Flying | Horsephotos

Sugar Plum Time (1972, Bold Ruler–Plum Cake, by Ponder), bred by Calumet Farm: A number of big winners trace to this mare, who was the first Phipps mare to win the then-Firenze, although she wasn't a homebred. Among her descendants are GISWs Grand Slam (Gone West), Christmas Kid (Lemon Drop Kid), and Kudos (Kris S.); MGSW Christmas Gift (Green Desert); and MSW & MGISP Bright Candles (El Gran Senor).

Kittiwake (1968, Sea Bird {Fr}–Ole Liz, by Double Jay), bred by Martin Andersen: This bay Florida-bred produced French G1SW Kitwood (Nureyev), six-time GISW Miss Oceana (Alydar), and MGSW & GISP Larida (Northern Dancer). Among the top horses tracing to her are European champion and MG1SW Dawn Approach (Ire) (New Approach {Ire}), GISW Aruna (Mr. Greeley), and English G1SW Magic of Life (Seattle Slew).

Obeah (1965, Cyane–Book of Verse, by One Count), bred by Bertram N. Linder: There may not be a big placeholder for this mare in the breeding annals as her two best foals to make it to the breeding shed–MGSW/MGISP Dance Spell (Northern Dancer) and GSW/GISP Discorama (Northern Dancer)–weren't able to leave a significant mark. Regardless, this mare will forever command a special place in racing due to her beloved champion daughter Go for Wand (Deputy Minister), who was lost too soon.

Straight Deal (1962, Hail to Reason–No Fiddling, by King Cole), bred by Bieber-Jacobs Stable: Desiree (Raise a Native) was the sole Grade I winner produced by this champion, whose multi-year racing campaigns meant she didn't have her first foal until age 10. However, her daughters certainly gave her an assist, with descendants including MGISW Adored (Seattle Slew); Breeders' Cup winner Dangerous Midge (Lion Heart); GISWs Qualify (Danzig), Scorpion (Seattle Slew), and Alwajeeha (Dixieland Band); MGSW and good sire Belong to Me (Danzig); and popular MGSW and GI Kentucky Derby runner-up Eight Belles (Unbridled's Song).

Blue Banner (1952, War Admiral–Risque Blue, by Blue Larkspur), bred by Mrs. John D. Hertz: This lovely bay produced a Broodmare of the Year in Key Bridge (Princequillo {GB}), who in turn produced Horse of the Year Fort Marcy (Amerigo {GB}), champion and influential sire Key to the Mint (Graustark), additional GISW Key to Content (Forli {Arg}), and GSW Key to the Kingdom (Bold Ruler). Others tracing to the then-Firenze winner include European champion and MG1SW Silver Patriarch (Ire) (Saddlers' Hall {Ire}), English highweight and G1SW Papineau (GB) (Singspiel {Ire}), and Brazilian champion Mensageiro Alado (Brz) (Ghadeer {Fr}).

Rare Treat (1952, Stymie–Rare Perfume, by Eight Thirty), bred by Erdenheim Farms Co: Among her descendants are European champion and G1 Epsom Derby winner Golden Fleece (Nijinsky II); U.S. champion What a Treat (Tudor Minstrel {Ire}); French G1SWs Mandaean (GB) (Manduro {Ger}) and Wavering (Ire) (Refuse To Bend {Ire}); U.S. GISWs Victory Speech (Deputy Minister) and Ida Delta (Graustark); and European MGSW Be My Guest (Northern Dancer), England's leading sire in 1982.

Parlo (1951, Heliopolis {GB}–Fairy Palace, by Pilate), bred by William duPont, Jr.: Horse of the Year Arts and Letters (Ribot {GB}), champion Silverbulletday (Silver Deputy), MGISW Waquoit (Relaunch), and Chilean champion All Glory (Honour and Glory) are among the top horses that trace to this diminutive chestnut, who also produced Broodmare of the Year All Beautiful (Battlefield).

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The Special Bond Uniting Two Travers Colts

How very apt, that a Saratoga card also featuring a race named in her honor should culminate Saturday in a GI Runhappy Travers S. bearing a twin imprint of the legacy of Personal Ensign. Both Dynamic One (Union Rags) and Miles D (Curlin), one-two in the Curlin S. last month, trace their ancestry to the Hall of Fame mare: Dynamic One's mother is out of Personal Ensign's granddaughter Storm Flag Flying (Storm Cat); while Miles D's dam is Storm Flag Flying's unraced half-sister Sound the Trumpets (Bernardini).

But if nobody could be surprised to see fresh tendrils of class on the family tree developed by Ogden Phipps from Dorine (Arg) (Aristophanes {GB})–the Argentine matriarch imported to Claiborne in 1970–then few will perhaps be aware that both these colts also find a more literal “bond” in a second remarkable female.

For the dams of both Dynamic One and Miles D are among just eight mares grazing the pasture of River Bend Farm, on the banks of the Ohio River near Goshen, north of Louisville. And while the farm's owner Ina Bond is in a position at least to ensure quality, if not quantity, then it is pretty astonishing for so small a band of broodmares to account for two of the six rivals to Essential Quality (Tapit)–especially when you consider that Bond has already bred one Grade I winner at Saratoga this summer, in Coaching Club American Oaks winner Maracuja (Honor Code).

In fairness, this apparent Midas touch did not prevent the sale of Maracuja's dam Patti's Regal Song (Unbridled's Song) for just $50,000 at the Keeneland November Sale of 2019. But if that has turned into a windfall for Checkmate Thoroughbreds, then at that same auction Bond herself achieved a similar coup in buying an 8-year-old mare named Beat the Drums (Smart Strike) for $400,000. She must have been delighted that the Phipps Stable had been willing to cull a mare whose latest yearling had raised as much as $725,000 at the September Sale. After all, while Beat the Drums had shown little in two career starts, the Phipps Stable was glad to retain a stake in the yearling with his purchasers Repole Stable & St. Elias Stable. And this colt, of course, has turned out to be none other than Dynamic One.

Beat the Drums, moreover, has started to pay her way already. The Honor Code colt she was carrying that November was sold as a yearling to Centennial Farms for $260,000; Bond is very pleased with her weanling colt by Ghostzapper; and the mare is in meanwhile foal to Street Sense.

Miles D, for his part, similarly helped to recoup Bond's investment in his dam. Sound the Trumpets had cost $675,000 at the Keeneland November Sale of 2017, with the bonus of a Curlin cover. The resulting foal was Miles D, who was sold through Denali to White Birch Farm as a September yearling for $470,000.

The next foal out of Sound the Trumpets, a Pioneerof the Nile colt, did not achieve quite the same traction, as a $120,000 RNA, and has been retained to race. “He's called Trumpets Blare, he's with Ian Wilkes and just getting ready to run shortly,” explained Bond, adding that Sound the Trumpets was given this cycle off after the late spring delivery of a fine colt by Medaglia d'Oro. The mare, after all, is still only eight.

“She also has a [Quality Road yearling] filly, that I think I'll keep,” Bond said. “I think I'd like to keep any fillies from that family. It just keeps producing, including in the last couple of years, not just runners but producers as well. And Sound the Trumpets is an extremely good-looking mare. We're very careful always to seek good conformation, because if they have an injury you're lost. Frankly I'm more of a commercial breeder than a racer, so I always try to get correct broodmares with a really strong pedigree–not just 'what have you done for me lately', the way a lot of people go for the hot new stallions. I spend a lot of time and get a lot of help doing the matings.”

There is hardly a stronger maternal line in the Stud Book, of course, than the sequence of three consecutive Breeders' Cup winners comprising Personal Ensign, My Flag (Easy Goer) and Storm Flag Flying. But if anyone should believe in pedigree, it is Ina Bond. For her own “page” is one of the most resonant in Kentucky: her great-grandfather George Garvin Brown founded Brown-Forman–think Woodford Reserve, Jack Daniels–and her grandfather Owsley Brown and father W.L. Lyons Brown both served as chairman. Bond in turn inherited an energetic commitment to both corporate and civic service, giving her time to a bewildering variety of business, community, educational and charity institutions. Now a septuagenarian, she admits that for much of her life, she has been too distracted to make the most of the sanctuary she has always relished on the farm since its acquisition in 1990.

“I got kind of overwhelmed,” she reflected. “I used to do a lot of volunteer work and was on a lot of different boards, commercial and non-commercial, I just got very busy and was always playing catch-up. Nowadays there are so many more tracks, so many horses and sires, everybody loves the betting. But it's a good thing, I suppose: it seems like whatever is going on in the world, the market for horses is very strong.

“I was always fascinated by horses, right from when I was little; in fact, I think I was in a horse show when I was in first grade. My mother was a good friend of Warner Jones, and I bought River Bend Farm from his son-in-law. It's a beautiful farm, but when I was starting out, the market was really bad. But though I had just a few mares, that first year one of them got us the second top price at the September Sale.

“I lived on the farm and it got me out a little bit, away from all these other things I was doing. But I also had children, and then eight grandchildren, as well as all those other different things stopping me from getting out with the horses as much as I'd like. But thankfully I did get some help. I have a nice crew who take care of the mares and foals; they never missed a day this summer no matter how hot it's been. And my farm manager Larry Weeden has helped me for 30 years; he's very good.”

Nurturing pedigrees is itself a task of conservation, and that is an area that has impassioned Bond's son Austin Mussulman–notably in the restoration of Ashbourne Farms in Oldham County, long part of the family and now a wedding, meeting and entertainment venue, securing the habitat alongside Harrods Creek. His wife Janie, meanwhile, comes from another storied Kentucky farm in Buck Pond, through which Maracuja–bred in partnership by Bond, her son and daughter-in-law–was sold as a Saratoga yearling for $200,000.

Buck Pond stands a surprise Travers winner in V.E. Day (English Channel) and now Bond, her family and her friends can root for another. The scrupulous standards of this boutique operation are certainly commensurate with the task facing Dynamic One and Miles D. Auspiciously, moreover, Bond reckons she has seldom had young stock on the farm of greater elegance and ease of motion than now. Look out, then, for the first foal of the young Ghostzapper mare Persephone's Dawn, an Into Mischief filly presented by Denali as Hip 488 at Keeneland September.

Aristocratic as these bloodlines are, any underdog can take legitimate inspiration from Bond's Saratoga summer: one mare cheaply culled after producing a subsequent Grade I winner, but promptly replaced by one whose own yearling son was even then embarking on a career that has meanwhile already taken in a shot at the Derby.

“That's what makes this business so attractive,” Bond observes. “You never know. When I sold the dam of Maracuja, she hadn't really produced much, but now she has a Grade I winner. I'm not a great big farm, like the ones around Lexington. We're not Juddmonte or Darley. I've basically been a small commercial breeder for 30 years. So needless to say, I'm quite excited by the Travers, though the competition is huge. I did not raise Dynamic One, but he's from that wonderful family; and I know Chad Brown is a great trainer, and he wouldn't have Miles D in there if he didn't think he had a shot, I think he really likes that colt. As I say, I've always been a small player. So this is a big deal for me, and I'd be thrilled if either of them were to be placed–or even give everyone a big surprise and win.”

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Curlin Colt Turns In ‘Jazzy’ Effort at Belmont

2nd-Belmont, $90,000, Msw, 6-12, 3yo/up, 1m, 1:36.94, ft, 2 1/4 lengths.
MILES D (c, 3, Curlin–Sound the Trumpets, by Bernardini) made a single visit to the races last season, a well-bet and close-up fourth at Aqueduct Oct. 11, in an event that has turned out to be no ordinary maiden. Next-out 'TDN Rising Star' and Smarty Jones S. winner Caddo River (Hard Spun) was runner-up to Godophin's Speaker's Corner (Street Sense) and a half-length better than Greatest Honour (Tapit), who would go on to annex the GIII Holy Bull S. and GII Fountain of Youth S. ahead of a third in the GI Curlin Florida Derby. Behind Miles D that day were the sixth-placed Bourbonic (Bernardini), this year's GII Wood Memorial S. upsetter, as well as Original (Quality Road), last of the octet, but since Grade III-placed on the turf. The late money came for Miles D, who was sent off the 1.15-1 chalk in advance of 8-5 fellow second-timer Southern Flag (Union Rags), and proved spot on. Settled back on the fence as Absolute Courage (Into Mischief) set the pace from off the rail, Miles D was asked to come after that one at the quarter pole, stuck a neck in front a furlong from home and kicked on nicely to take it by 2 1/4 lengths. Absolute Courage boxed on gamely at the rail to claim second spot, a head better than Southern Courage, who was slowly into stride, raced three and four wide the trip and was forced to settle for third. Miles D is the first foal for his unraced dam, a half-sister to champion Storm Flag Flying (Storm Cat) who was purchased with this colt in utero for $675,000 at the 2017 Keeneland November Sale. Sound the Trumpets's 2-year-old son Trumpets Blare (Pioneerof the Nile) breezed three-eighths of a mile in :37.40 at the Skylight Training CenterSaturday morning and her most recent produce include a yearling Quality Road filly and a colt foal by Medaglia d'Oro. Miles D's third dam was the irrepressible Personal Ensign (Private Account), who was also responsible for Grade I winners Miner's Mark (Mr. Prospector) and Traditionally (Mr. Prospector) as well as MGSP Salute (Unbridled), whose produce include Lane's End stallion and GISW Mr Speaker (Pulpit), GSW Fire Away (War Front) and SW/GSP Vigilantes Way (Medaglia d'Oro). Miles D is bred on the same cross as GISW Paris Lights and other graded winners Point of Honor, Clairiere, 'TDN Rising Star' Spice Is Nice and Cezanne. Sales history: $470,000 Ylg '19 KEESEP. Lifetime Record: 2-1-0-0, $53,280. Click for the Equibase.com chart or VIDEO, sponsored by TVG.
O-Peter M Brant & Robert V LaPenta; B-River Bend Farm (KY); T-Chad C Brown.

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