By B. Jason Brooks

SARATOGA SPRINGS, N.Y. – Phipps Stable’s homebred Mystifying is making her third career start and first on the turf in Race 11 on Monday, September 2nd, the closing day of the Saratoga meet.

The lightly-raced Curlin filly had shin trouble last year, postponing her debut until January of this year.

Making her first start a winning one over six furlongs on the dirt at Gulfstream Park, she dueled inside a pair of foes while racing in the two-path before kicking clear in the upper stretch and digging in to repel a late challenge for a half-length victory.

In a February interview (here) with Horse Racing Nation’s managing editor Ron Flatter, Mystifying’s Hall of Fame trainer Shug McGaughey stated, “I’d like to have the opportunity coming off that three-quarter [of a mile] race to have a little bit of time in between to let her get over that. We’ll try to come back a little bit farther.”

She returned in mid-March among allowance company over seven furlongs on the dirt at Gulfstream, driving four wide in the turn and weakening in the stretch to finish seventh.

Following the March effort, she went two months without any timed breezes before clocked workouts resumed in mid-May at Niall Brennan Stables in Ocala.  Since then, she has put in a steady series of near-weekly workouts, returning to Mr. McGaughey’s barn at Belmont in June and at Saratoga for the current meet.  (See her four-furlong August 25th breeze over the turf with stablemate Statesman, a juvenile colt by Constitution, on XBTV here.)

Ending a 170-day layoff, Mystifying will have jockey Tyler Gaffalione aboard, breaking from post No. 5 in a field of a dozen for the mile-and-a-sixteenth allowance race for fillies and mares of ages three years and older.  Post time is 6:17 pm Eastern.

She enters the race with 10-to-1 morning-line odds.  In his TimeformUS Race Analysis (here), David Aragona notes that Mystifying “has plenty of Phipps turf pedigree in her female family, and has also worked well on the surface ahead of this start. Shug McGaughey also has strong statistics coming off layoffs in turf routes.”

Mystifying is the sixth foal out of stakes-placed Ghostzapper mare Puzzling, with all of them being winners. Puzzling’s seventh foal, a 2022 Street Sense colt named Cipher, was purchased by Centennial Farms for $500,000 from the Claiborne Farm consignment at the 2023 Keeneland September yearling sale and is in training.

A sixth-generation Phipps homebred, Mystifying hails from the elite female family tracing back to blue-hen mares Blitey, by Riva Ridge, and Lady Pitt, by Sword Dancer, the latter being the 1966 champion 3-year-old filly acquired privately in 1969 from Golden Triangle Stable by Ogden Phipps.

Lady Pitt’s descendants include 2022 Horse of the Year Flightline, by Tapit, grade 1-winning sires Oscar Performance, by Kitten’s Joy, and Instilled Regard, by Arch, grade 1 American Oaks winner Queen Goddess, by Empire Maker (who sold for $1.525 million at the 2022 Fasig November Sale), and nine grade 1-winning Phipps homebreds, including Hall of Famer Heavenly Prize, by Phipps sire Seeking the Gold, as well as Dancing Forever, by Rahy, Dancing Spree, by Nijinsky II, Fantastic Find, by Mr. Prospector, Finder’s Fee, by Storm Cat, Furlough, by Phipps sire Easy Goer, Good Reward, by Storm Cat, Oh What A Windfall, also by Seeking the Gold, and Persistently, by Smoke Glacken.

Photo: Mystifying at Saratoga, July 2024, courtesy of Daisy Phipps Pulito

Phipps Stable and St. Elias Stable would like to thank New Vocations for finding the perfect home for Dynamic One. The retired grade 2 winner has been adopted from New Vocations Racehorse Adoption Program by Madison Thompson for a new career in eventing.

The former owners also thank Ms. Thompson for adopting the 6-year-old gelding, giving him a great new home, and journeying with him in his second career.

Posted along photos of herself and Dynamic One happily together on Instagram, Ms. Thompson wrote “Welcome to the family Dynamic One! When things are meant to be, they fall into place at the right time. Huge thanks to New Vocations for bringing this special horse into my life.”

After being retired in April, Daisy Phipps Pulito stated, “Phipps Stable bred him and sold him… We were lucky enough to be able to stay in and enjoy him racing. He gave my family a lot of memories and enjoyment watching him run and rooting for him. I think everyone from owners, breeders and trainers, exercise riders, bloodstock agents and grooms should be good stewards of the industry, its history and its future. Dynamic One doesn’t owe us anything but we owe him a good retirement.”

Read more in Joe Nevills’ Paulick Report story on Dynamic One’s journey this year which has brought him from the Pegasus World Cup Invitational, to the Keeneland sales ring, to the New Vocations Racehorse Adoption Program, where he has been successfully adopted from by a great new owner for a second career: “‘We Owe Him A Good Retirement’: Kentucky Derby Runner Dynamic One Retired To New Vocations After Keeneland April Sale“

By B. Jason Brooks

SARATOGA SPRINGS, N.Y. – Ending a 45-day layoff after finishing runner-up by a head last time out, overwhelming 1-to-5 favorite Pentathlon lived up to expectations, cruising home to a three-and-a-half-length victory under newly-elected Hall of Fame jockey Joel Rosario.

In the one-mile maiden special weight race starting in the chute, Pentathlon broke well and dropped from the two-path to the inside, rating just off the pace and saving ground while drafting behind the leader through the first turn, up the backstretch, and through the far turn.  He was urged while moving back to the two-path at the top of the stretch, closing in on the leader before going to the front outside of the sixteenth pole and drawing clear for his first victory.  The chestnut Speightstown colt finished in 1 minute and 37.06 seconds.

The race was the third of his 3-year-old campaign and fifth of his career.  The win brings his career record to one win, one runner-up, and two third-place finishes.

Bred by Phipps Stable and co-owned by the breeder, Vincent Viola’s St. Elias Stables, and the Farish family’s Woodford Racing partnership, he was foaled on February 6, 2021 in Paris, Kentucky at Claiborne Farm.  Pentathlon was broken and pre-trained in Ocala, Florida at Niall Brennan Stables and is trained by Hall of Famer Claude R. “Shug” McGaughey.

A sixth-generation Phipps bred out of stakes-placed Tapit mare Parade, Pentathlon is from the Personal Ensign branch of the female family tracing back to imported Argentine-bred Dorine, by British sire Aristophanies, acquired by Ogden Phipps in 1970.

See yesterday’s story “Promising Phipps Colt Pentathlon Chasing First Score” on the Phipps Stable Fan blog for more on Pentathlon’s racing career and pedigree.

Photos by B. Jason Brooks

by B. Jason Brooks

SARATOGA SPRINGS, N.Y. – After knocking on the door of his first trip the winner’ circle earlier this summer, Phipps homebred Pentathlon is ending a 45-day layoff for the third start of his sophomore campaign on Thursday, August 15th in Race 3 at Saratoga Race Course.

The maiden special weight race covering one mile on the dirt for ages three years and older has a purse of $100,000 and a post time of 2:22 pm Eastern.  Pentathlon is breaking from post position No. 2 in a field of eight entries for Hall of Fame trainer Shug McGaughey.

The Speightstown colt came up a head short last time out at Aqueduct on June 30th, breaking from the outside post in field of five entries.  He stalked the pace from the three-path before nudging ahead for the lead entering the stretch.  He dug in for a stretch duel, bumping with a foe as they raced shoulder to shoulder six lengths ahead of the rest of the field before finishing a close second.  His runner-up effort came after finishing third in his previous two starts. 

He enters the race on Thursday as a 2-to-5 morning-line favorite.  Wearing saddle cloth No. 1, Pentathlon is a paired entry with 3-year-old Curlin colt Upstanding, a Todd Pletcher-trainee co-owned by St. Elias Stables who also co-owns Pentathlon with Phipps Stable and Woodford Racing.

Pentathlon has been training well since his last start, putting in three timed workouts on Saratoga’s Oklahoma training track, including a four-furlong bullet on July 24th in 48.25 seconds.

Newly-inducted Hall of Fame jockey Joel Rosario has the mount.  He rode Pentathlon two races ago (pictured below) to a third-place finish at Saratoga in which the colt earned his highest career Beyer speed figure of 84.  Mr. Rosario has a record of success with the stable, sharing in the connection’s 2013 Kentucky Derby victory after guiding Orb to a memorable two-and-a-half-length win.

Well-bred Pentathlon shares the same sire (Speightstown) and female family as Phipps homebred multiple graded stakes winner Performer who suffered a career-ending ankle injury at the age of 5.  Retiring with six wins from nine starts in 2021, he was to stand at Claiborne Farm but tragically died from a ruptured stomach prior to his first season at stud.

A sixth-generation Phipps-bred, Pentathlon is the second foal out of graded stakes-placed Parade, by Tapit.  Pentathlon’s second dam is graded stakes-placed On Parade, by Storm Cat, third dam is Breeders’ Cup champion My Flag, by Easy Goer, and fourth dam is undefeated Hall of Famer Personal Ensign, By Private Account, all trained by Shug McGaughey.  The family traces back to imported Argentine-bred Dorine, by British sire Aristophanies, acquired in 1970 by Ogden Phipps.

The deep, winning Phipps female family also includes Storm Flag Flying, by Storm Cat, Personal Flag, by Private Account, Miner’s Mark, by Mr. Prospector, Traditionally, by Mr. Prospector, as well as sires Mr Speaker, by Pulpit, Arabian Lion, by Justify, and Seeking the Soul, by Perfect Soul, all of which are grade 1 winners.

(Race replay of Pentathlon’s runner-up finish last time out on June 30, 2024 at Aqueduct.)

The 103rd Saratoga Sale kicks off on Monday, August 5th and Phipps female families are well represented with 17 yearlings in the catalog, including 9 colts and 8 fillies (listed below).

A total of 8 different Phipps families are represented, including four yearlings from the family of Helvetia, three each from the families of Dorine (Arg) and Erin, two each from the families of Baby League and Big Hurry, and one each from the families of Businesslike, Grey Flight, and Marguerite de Valois (Fr). 

Some of the great Phipps mares represented include undefeated Hall of Famer Personal Ensign and grade 1 winners Dance Number, Educated Risk, and My Flag.  

Seven of the Phipps female families represented include influential reines-de-course or “queens of the turf” mares, identified by the late pedigree expert Ellen Parker for their lasting impact as broodmares.  Parker recognized that their influence goes well beyond the few generations found in the sales catalogs.  Among the families represented in the Saratoga Sale, the reines mares bred or acquired by the Phippses (grouped by family) include: Numbered Account, Intriguing, Glamour, Striking, and Baby League; Searching and Big Hurry; Personal Ensign, Grecian Banner, and Dorine (Arg); Bold Irish and Erin; Pure Profit, Clear Ceiling, and Grey Flight; Lady Be Good; and, Hostility and Marguerite de Valois (Fr).

In addition to their elite Phipps families, these Saratoga Sale yearlings are sired by top stallions, including Bolt d’Oro, Gun Runner, Into Mischief, Justify, Medaglia d’Oro, Oscar Performance, Quality Road, Speightstown, and War Front, among others.

A reason horses from Phipps families remain so attractive to buyers is the fact that they continue to succeed at the top levels of racing in the U.S. and internationally. Last year, horses from Phipps families won a total of 95 graded or group stakes races in top-tier racing countries (see the full list here). The impressive list includes 21 elite grade 1 or group 1 wins, including 8 in the U.S.

Additionally, Saratoga Sale graduates from Phipps families have been well represented among grade 1 winners in recent years.  This elite club includes a half dozen top winners since 2019, including 2024 Preakness Stakes winner Seize the Grey, undefeated 2022 Horse of the Year Flightline, 2023 Shoemaker Mile Stakes winner Exaulted, 2021 Amesrican Oaks winner Queen Goddess, 2021 Churchill Downs Stakes winner Flagstaff, and 2019 Breeders’ Cup Juvenile Fillies winner Sharing. 

Other Saratoga Sale graduates from Phipps families have gone on to win multiple grade 2 and/or grade 3 stakes races in recent years, including Major Dude, Pink Sands, and Tizamagician.

The Saratoga Sale offers a great deal of promising bloodstock that will be exciting to see go through the sales ring on Monday and Tuesday nights and fun to follow at the track in years to come.

2024 SARATOGA SALE YEARLINGS FROM PHIPPS FAMILIES

Hip #17 – b. f. (KY) War Front – Complicated, by Blame, 1st-6th dams: Complicated / Consequence / Educated Risk / Pure Profit / Clear Ceiling / Grey Flight, Consignor Indian Creek, Barn 6

Hip #25 – b. f. (KY) Gun Runner – Curlina, by Cuvee, 3rd-9th dams: Private Seductress / In Full Cry / In Hot Pursuit / Lady Be Good / Past Eight / Helvetia, Consignor Mulholland Springs, Barn 4

Hip #41 – dkb. c. (KY) Quality Road – Evocative, by Pioneer of the Nile, 5th-7th dams: Leix / Bold Irish / Erin, Consignor Turning Point, Barn 3

Hip #43 – b. c. (KY) Oscar Performance – Fastbridled, by Unbridled’s Song, 2nd-6th dams: Broad Pennant / Pennant Champion / Personal Ensign / Grecian Banner / Dorine (ARG), Consignor Mill Ridge, Barn 5

Hip #60 – b. f. (KY) Quality Road – Grand Prix, by Tale of the Cat, 4th-8th dams: Fiddlesticks / Discipline / Lady Be Good / Past Eight / Helvetia, Consignor Buck Pond, Barn 3

Hip #86 – b. c. (NY) Street Sense – Maximova, by Danehill Dancer (IRE), 8th-10th dams: Boldness / Hostility / Marguerite de Valois (FR), Consignor Denali, Barn 7A

Hip #106 – ch. f. (KY) Justify – Nina Fever, by Borrego, 6th-8th dams: Comic Relief / His Duchess / Businesslike, Consignor Hunter Valley, Barn 2

Hip #110 – dkb. c. (KY) More Than Ready – Off Topic, by Street Sense, 3rd-7th dams: Swinging / Pennant Champion / Personal Ensign / Grecian Banner / Dorine (ARG), Consignor Scott Mallory, Barn 5

Hip #116 – b. f. (KY) Medaglia d’Oro – Piece By Peace, by Declaration Of War, 6th-7th dams: No Fiddling / Big Hurry, Consignor Machmer Hall, Barn 5

Hip #122 – b. f. (KY) Medaglia d’Oro – Princess Julia, by Distorted Humor, 6th-9th dams: Stolen Base / Bases Full / Striking / Baby League, Consignor Taylor Made, Barn 7B

Hip #138 – b. c. (KY) Bolt d’Oro – Sail On, by Into Mischief, 3rd-7th dams: With Flying Colors / My Flag / Personal Ensign / Grecian Banner / Dorine (ARG), Consignor Taylor Made, Barn 7B

Hip #145 – b. c. (KY) Munnings – Secret Jewel, by Bernardini, 5th-7th dams: Leix / Bold Irish / Erin, Consignor Taylor Made, Barn 10

Hip #152 – b. f. (KY) Oscar Performance – Shop Again, by Wild Again, 3rd-6th dams: Impish / Lady Be Good / Past Eight / Helvetia, Consignor Mill Ridge, Barn 5

Hip #153 – b. c. (KY) Into Mischief – Shopit, by Yes It’s True, 4th-7th dams: Impish / Lady Be Good / Past Eight / Helvetia, Consignor Blake-Albina, Barn 7A

Hip #194 – ch. f. (KY) Speightstown – Tooken, by Giant’s Causeway, 3rd-9th dams: Oscillate / Dance Number / Numbered Account / Intriguing / Glamour / Striking / Baby League, Consignor Buckland Sales, Barn 4

Hip #215 – b. c. (KY) Charlatan – All Laced Up, by Bernardini, 6th-8th dams: Leix / Bold Irish / Erin, Consignor Gainesway, Barn 6

Hip #225 – ch. c. (KY) Munnings – Azaelia (FR), by Turtle Bowl (IRE), 7th-8th dams: Searching / Big Hurry, Consignor Elite, Barn 8

Photo: From the Phipps family of Blitey and Lady Pitt, undefeated champion FLIGHTLINE sold for $1 million at the 2019 Saratoga Sale.

Phipps Stable’s co-owned stakes winner Perform is looking to get back to his winning ways in Race 3 on Friday, August 2 at Saratoga.

The allowance optional claiming race for ages three years and older has a purse of $115,000 and will cover a mile and an eight on the dirt. Perform will break from the inside post with jockey Dylan Davis aboard for trainer Shug McGaughey.

Perform enters the five-horse race as the second favorite with odds of 5/2. Post time is 2:18 pm Eastern.

He broke his maiden in his sixth career start and second as a sophomore last March at Tampa. He followed it up with a victory in the Federico Tesio Stakes at Laurel Park in April, a win that qualified him for the grade 1 Preakness. He struggled to become factor in the deeper waters, finishing sixth in a field that included Kentucky Derby winner Mage and, now a three-time grade 1 winner, National Treasure. In his last start as a 3-year-old, he finished off the board in the Curlin Stakes at Saratoga in July.

The colt by Hill ‘n’ Dale Farms stallion Good Magic ended a 10-month layoff in May and has finished second or third in each of his three monthly starts so far this year.

Perform’s granddam is a half-sister to sires Into Mischief and Mendelssohn, as well as four-time champion Beholder. He was purchased for $230,000 at the 2021 Keeneland September sale and is owned in partnership by Woodford Racing LLC, Lane’s End Farm, Phipps Stable, Ken Langone, Lynne Hudson, and Edward Hudson, Jr.

Photo: Perform in his June 7th start at Saratoga.

Stuart S. Janney III and Phipps Stable’s homebred Tom Collins is making his 3-year-old debut on Friday, July 12 in Race 3 at Saratoga, a maiden special weight covering a mile and a sixteenth on the turf.

Tom Collins is ending a nine-month layoff after finishing runner-up in his last start, a turf race at Aqueduct. He progressed nicely as a juvenile last summer at Saratoga, taking sixth in his career debut in August and third next time out in September.

He’ll break from the inside post with jockey Joel Rosario aboard for trainer Shug McGaughey, the same connections that won the 2013 Kentucky Derby with Orb.

By Darley stallion Frosted, he’s out of Tiznow mare Party Now, the dam placing in multiple stakes and earning three wins from eight career starts. Tom Collins’ tail-female line is all Janney and Phipps, going back seven generations to La Troienne mare Belle Histoire, acquired in 1946 by Ogden Phipps. The family includes 2003 French champion 3-year-old Bright Sky and U.S. grade 1 winners Carriage Trail and Her Smile.

Phipps Stable’s 4-year-old Into Mischief filly Self Confident followed up her maiden win last time out with a determined allowance victory on Friday at Laurel.

Breaking from the rail in a mile and a sixteenth turf race with jockey Forest Boyce aboard, she broke from the rail and saved ground around the first turn. She stalked the pace from her rail position down the backstretch and far turn before moving to the three path entering the stretch. She made a bid for the lead inside the eighth pole and prevailed to win by a neck.

After sitting out her sophomore campaign, she has progressed nicely this year, taking fourth in two starts at Gulfstream in January and February, followed by a third-place finish at Tampa in April. Her maiden win came in May at Monmouth, getting up at the wire to win by a head.

Self Confident is a half-sister of Phipps Stable’s stakes-placed Speightstown horse Dreams of Tomorrow and her dam Sabbatical, by Medaglia d’Oro is a half-sister to grade 1 winner Imagining, by Giant’s Causeway. A ninth-generation Phipps homebred, Self Confident is from the Get Lucky branch of La Troienne mare Baby League.

Photo: Jockey Forest Boyce aboard Self Confident after her allowance win at Laurel.

One of Phipps Stable’s most promising 3-year-olds this year is Speightstown colt Pentathlon, who moved forward with a runner-up effort over a mile on the dirt at Aqueduct on Sunday, June 30th, the second start of his sophomore campaign.

Breaking from the outside post in field of five with jockey Kendrick Carmouch aboard, Pentathlon patiently stalked the pace from the three path out of the chute, up the backstretch, and into the far turn. He responded to urging in the turn and nudged ahead for the lead before brushing with a foe in a stretch duel, coming up a head short in an exciting finish.

The colt is the second foal out of Parade, a graded stakes-placed Tapit mare and half-sister of multiple graded stakes-winning horse Parading, by Pulpit. His second dam is graded stakes-placed Storm Cat mare On Parade, third dam is Breeders’ Cup champion My Flag, and fourth dam is undefeated Hall of Famer Personal Ensign. This elite family traces back to imported Argentinian mare Dorine, acquired by Ogden Phipps in 1970.

Trained by Hall of Famer Shug McGaughey, Phipps-bred Pentathlon is owned in partnership by Phipps Stable, St. Elias Stable, and Woodford Racing.

Partnership-owned 4-year-old Medaglia d’Oro colt Juan Valdez is seeking his first win on Friday, June 20th in Monmouth Park’s Race 5, a maiden special weight for ages three years and older covering a mile and a sixteenth on the turf. Post time is 3:53 pm Eastern.

After rallying in the stretch to come up a nose short on March 16th at Gulfstream Park, he took a step back last time out on May 10th at Churchill Downs, tiring in the stretch to finish off the board.

Since returning to Belmont after the race to continue training with Hall of Famer Shug McGaughey, he has put in a series of four workouts, including breezing four furlongs over the dirt training track in 48.48 seconds, the third fastest of 37 on June 4th.

Jockey Paco Lopez has the mount. breaking from post No. 5 in a field of 9. Mr. Lopez was aboard Juan Valdez for his runner-up finish in March.
Juan Valdez enters the race with morning-line odds of 3-to-1, the second favorite behind fellow Don Alberto-bred Main Beach, a 3-year-old Into Mischief gelding out of sold Cynthia Phipps-bred mare Siren Serenade, by Unbridled’s Song. The dam is a daughter of Phipps’ four-time grade 1-winning millionaire Versailles Treaty. The race also includes 4-year-old Speightstown colt Paxsational, the first foal out of sold stakes-placed Phipps mare Browse, by Medaglia d’Oro. Paxsational’s younger half-sister is Quality Road filly Pipit, winner of the listed 2023 Victoria Stakes at Woodbine.

Juan Valdez is a half-brother of multiple grade 1-winning millionaire and sire Constitution, by Tapit. He was purchased for $900,000 from the Hartley Derenzo Thoroughbreds consignment at the March 2022 Fasig-Tipton Florida Select 2-Year-Olds in Training Sale and is owned in partnership by West Point Thoroughbreds, Inc., Woodford Racing LLC, Lane’s End Farm, #PhippsStable, Ken Langone, Edward Hudson Jr., and Lynne Hudson.

Photo: Juan Valdez, January 2023