Ghostzapper mare Wayfaring hails from a deep, successful Phipps family described by pedigree analyst Kaitlin Free “as one of the greatest in recent history.”  Being offered as Hip 16 in Book 1 of the Keeneland November Breeding Stock Sale on Tuesday, November 4, she is consigned by Lane’s End and is in foal to Horse of the Year Flightline.

Wayfaring is a half-sister to Surprisingly, by Mastery, who launched a fierce closing rally to win her graded debut in the 2023 Endeavor Stakes (G3) for Hall of Fame trainer Shug McGaughey.  She was purchased later that year by Repole Stable as a racing or broodmare prospect for $1 million from the Claiborne Farm consignment at the 2023 Keeneland November Sale.

Wayfaring’s dam Vagabond, by Arch, is half to Alpha Delta Stables’ Great Island, by Scat Daddy, who was runner-up in the 2021 Flower Bowl Stakes (G1) behind the classy three-time grade 1 winner War Like Goddess, by English Channel.  In her prior race, Great Island defeated three graded winners thanks to an impressive rally that took her from last to first to win going away in the Matchmaker Stakes (G3).

Second dam Voyage, by Rahy, is a half to two multiple grade 1 winners, a stakes winner, and a stakes-placed finisher who produced a stakes winner.  Her most successful sibling is five-time grade 1-winning sire Point of Entry, by Dynaformer, who retired in 2013 with nearly $2.5 million in career earnings.  His marquee victories included three successive grade 1 victories in 2012 – including the Man o’ War Stakes (G1), Sword Dancer Invitational Stakes (G1), and Joe Hirsch Turf Classic Invitational Stakes (G1).  He finished his campaign that year with runner-up honors in the Breeders’ Cup Turf (G1). 

Point of Entry’s 2013 campaign kicked off in the Gulfstream Park Turf Handicap (G1) – renamed the Pegasus World Cup Turf starting in 2019 – with an impressive victory over a field that included 2011 Kentucky Derby winner and Eclipse champion Animal Kingdom.  He picked up his fifth career grade 1 win next time out with a come-from-behind victory in the Manhattan Handicap (G1).  An Eclipse award finalist in 2012 and 2013 for male turf horse (won both years by Hall of Famer Wise Dan), Point of Entry entered stud in Kentucky in 2014 at Adena Springs and is the sire of two champions and a dozen graded or group stakes winners in the U.S., Canada, Japan, and United Arab Emirates.

Voyage’s half-sister Pine Island, by Arch, won the prestigious Alabama Stakes (G1) and Gazelle Stakes (G1), and finished runner-up in the Mother Goose Stakes (G1) and fillies classic Coaching Club American Oaks (G1).  Voyage’s half-brother Bokeelia Island, by Medaglia d’Oro, went from last to first to earn his first stakes victory in the 2019 JR Malouff Handicap and won the Veterans Stakes later that year.  Her other half-sister Chili Cat, by Storm Cat, placed in the A Wild Ride Stakes and produced Cat’s Claw, by Dynaformer, who rallied to win the 2014 Waya Stakes at Saratoga. 

Wayfaring’s winning third dam Matlacha Pass, by Seeking the Gold, is a full sister to Pleasant Home who won the 2005 winner of the Breeders’ Cup Distaff (G1) by 8 lengths.  That year, she also won the Bed o’ Roses Stakes (G3) and was runner-up in the Ballerina Stakes (G1) and Spinster Stakes (G1).

Though her daughter Magical World, by Distorted Humor, Pleasant Home is the granddam of a multiple grade 1-winning Three Chimneys Farm-bred Guarana, by Ghostzapper.  She was a 6-length winner of the 2019 Acorn Stakes (G1) in her second career start, followed by a victory in the Coaching Club American Oaks (G1).  In 2020, Guarana added a third grade 1 win in the Madison Stakes (G1), bringing her career earnings to more than $1 million.  Guarana sold the following year in foal to Into Mischief for $4.4 million at the Faisg-Tipton November Sale.  Her dam Magical World, who was also in foal to Into Mischief, sold at the same sale for a whopping $5.4 million.

In addition to Guarana, Magical World produced Pioneer of the Nile colt Beatbox, who was purchased at the 2019 Keenland September Yearling Sale for $2.1 million and won the 2024 Fair Grounds Stakes (G3).  Magical World’s third stakes winner Magic Dance, by More Than Ready, placed in the 2019 Adirondack Stakes (G3) after a victory Churchill’s Debutante Stakes.

Matlacha Pass’s full sister Country Hideaway was a four-time graded winner, with victories in the First Flight Handicap (G2) in 1999 and 2000, Vagrancy Handicap (G2) in 2000, and Bed o’ Roses Handicap (G3) in 2001.  She was also three-time grade 1-placed after finishing runner-up in the Ballerina Handicap (G1) in 2000 and 2021 and placing in the Ruffian Handicap (G1) in 2000.  Country Hideaway is the dam of Boca Grande, by A.P. Indy, who had victories in the 2006 Demoiselle Stakes (G2) and 2007 Comely Stakes (G2).  In addition to her graded wins, Boca Grande placed in the Mother Goose Stakes (G1) and Test Stakes (G1) in 2007.  Through Boca Grande’s branch of her family, Country Hideaway is the third dam of Osamu Satomi’s Satono Tempest (JPN), winner of the 7-furlong Takasegawa Stakes in 2023 in his native Japan.  Country Hideaway also foaled Vacation, by Dynaformer, who rallied five wide to convincingly win Arlington Park’s 2009 Hanshin Cup Handicap (G3) by 2¼ lengths.

Also by Seeking the Gold, Matlacha Pass’s other full sister Home Sweet Home is the dam of Birdie Birdie (JPN), by Brian’s Time, winner of the 2010 Unicorn Stakes (G3) in Japan.  He also won four other stakes and retired with nearly US $2.9 million in earnings.

Wayfaring’s fourth dam is Our Country Place, by Pleasant Colony, was acquired by Ogden Phipps in 1993.  She was a half-sister to Sugar Maple Farm-bred Hall of Famer Sky Beauty, by Blushing Groom (FR).  Trained by Allen Jerkens, Maplejinsky was a nine-time grade 1 winner, including the New York Triple Tiara (Acorn Stakes {G1}, Mother Goose Stakes {G1}, Coaching Club American Oaks {G1}) and Alabama Stakes (G1).  Our Country Place and Sky Beauty are half to Silence Beauty (JPN), by Sunday Silence, dam of Charles Fipke’s homebred Tale of Ekati, by Take of the Cat, who won the Wood Memorial (G1) and Cigar Mile Handicap (G1) and entered study in Kentucky in 2011 at Darby Dan Farm.

Wayfaring’s fifth dam Maplejinsky, by Nijinsky II, was half-sister to 1990 English Horse of the Year Dayjur, by Danzig, and her sixth dam was champion sprinter Gold Beauty, by Mr. Prospector.

Yearlings from Phipps Female Families Are Hot, With Three Session 1 Yearlings Topping $1 Million

On the heels of a wildly successful Saratoga Sale where eight yearlings from Phipps female families averaged more than $1 million, yearlings from Phipps families remained hot at Monday’s opening session of the Keeneland September Sale, with two colts and one filly each selling for seven figures.

Hip 177 – Session-Topping Gun Runner Colt

The Session 1 sale topper was a Gun Runner colt (Hip 177) from the Hill ‘n’ Dale Farm consignment who fetched $3.3 million.  Co-bred by Hill ‘n’ Dale and Determined Stud, the colt was purchased by Coolmore’s M.V. Magnier, White Birch Farm’s Peter Brant, and Winchell Thoroughbreds.  The colt’s second through fifth dams are Phipps, from Blitey branch of foundation mare Lady Pitt.

The Gun Runner colt is out of Tapit mare Thoughtfully, a five-length winner of the 2020 Adirondack Stakes (G2) at Saratoga.  From five crops of racing age, Gun Runner has sired six graded stakes winners who are out of Tapit mares, including Peter Blum’s homebred Society, winner of the 2024 Ballerina Handicap (G1). 

Thoughtfully is out of Phipps Stable-bred Seeking the Gold mare Pension and is a full sister to Signator who has found success this year since moving to the turf for Hall of Fame trainer Shug McGaughey.  After winning his turf debut at Tampa in March, the 5-year-old horse earned his first stakes victory in April in the Henry S. Clark Stakes at Laurel.  Declared a “Rising Star” by Thoroughbred Daily News after impressively breaking his maiden at second asking at the age of 2, Phipps Stable is among the horse’s owner partnership that also includes West Point Thoroughbreds, Woodford Racing, Gainesway Stable, Ken Langone, Edward Hudson Jr., and Lane’s End Racing.

Thoughtfully is also a half-sister to Godolphin’s 2015 Futurity Stakes (G2) winner Annual Report, by Harlan’s Holiday, and multiple stakes winner Giant Payday, by Giant’s Causeway. 

The Gun Runner colt’s third dam is Furlough, a grade 1 winner by Easy Goer, and fourth dam is blue hen mare Blitey, a multiple graded stakes winner by Riva Ridge.  Blitey is the ancestress of an elite family that includes nine grade 1 winners for the Phippses, including Hall of Famer Heavenly Prize, by Seeking the Gold.  Some of Blitey’s other descendants having grade 1 success in recent years include Horse of the Year Flightline, by Tapit, Instilled Regard, by Arch, and Queen Goddess, by Empire Maker.

Hip 10 – Flightline Colt Who is Half to Dual-Breeders’ Cup Winner Golden Pal

Another colt from a Phipps family to achieve seven figures was Hip 10.  Representing the first crop of Flightline, the colt was purchased by Resolute Bloodstock for $1.5 million from the consignment of VanMeter Sales.  The colt is a half-brother to dual Breeders’ Cup-winning sire Golden Pal, by Uncle Mo, who is out Midshipman mare Lady Shipman, winner of the 2016 Royal North Stakes (G3).

The second dam Sumthingtotalkabt, by Mutakddim, is a California-bred half-sister to stakes winner Rules of War, by Cromwell, and the third dam is California-bred multiple stakes winner Nannetta, by Falstaff.  The damline traces back to the Striking branch of Phipps foundation mare Baby League and the extended family includes Ogden Phipps-bred Landscaper, by Herbager, winner of the 1978 Century Handicap (G1).

Hip 115 – Tapit Filly Out of Second-Generation Breeders’ Cup Winner Sharing

In addition to the two colts, a filly from a Phipps family that sold for seven figures was Hip 115.  By Tapit, the filly was purchased by Whisper Hill Farm for $1.5 million from the consignment of Gainesway.  The dam is Eclipse Thoroughbred Partners and Gainesway Stable’s 2019 Breeders’ Cup Juvenile Fillies Turf (G1) winner Sharing, by Speightstown, and her second dam is Sagamore Farm’s Breeders’ Cup Filly and Mare Turf (G1) winner Shared Account, by Pleasantly Perfect. 

The Tapit filly has the rare opportunity to potentially become a third-generation Breeders’ Cup winner, a feat accomplished on only one prior occasion by Phipps homebreds Personal Ensign, her daughter My Flag, and her granddaughter Storm Flag Flying.

The yearling filly’s damline traces back to the Bold Irish branch of Phipps foundation mare Erin and the extended family includes grade 1 winners Randomized, by Nyquist, Got Stormy, by Get Stormy, and New Years Day, by Street Cry (IRE), among others.

Coolmore and White Birch’s Recent Phipps Bloodline Purchases

In addition to their session-topping $3.3 million Gun Runner colt, like many top owners and breeders, the Coolmore connections and White Birch Farm have shown an affinity for Phipps bloodlines.  Their new acquisition came just a month after they teamed up for the $4.1 million Saratoga Sale-topping Into Mischief colt (Hip 218) whose second through fourth dams are Phipps, from Versailles Treaty branch of Ten Cents A Dance.  They also went to $1.3 million at last year’s Keeneland September sale for a Curlin colt (Hip 262) who is a half to the Gun Runner colt they purchased on Monday.

Following the Saratoga Sale, Peter Brant highlighted his and the Coolmore team’s affinity for Phipps female families, noting that the Into Mischief colt’s damline “[g]oes back to great old Phipps blood we really like.”  (For more on the colt’s family and the overall success of Phipps bloodlines at the 2025 Saratoga Sale, see the recent BloodHorse story “Saratoga Sale Yearlings from Phipps Families Average More Than $1 Million”.)  

Hip 664 – Phipps-Bred Maxfield Colt Selling Wednesday

Another opportunity for a well-bred yearling with Phipps bloodlines will be offered in Session 3 of the Keeneland Sale on Wednesday with Hip 664, a ninth-generation Phipps-bred by Maxfield out of War Front mare Cover Model.  Hailing from the Get Lucky branch of Phipps foundation mare Baby League, he is from one of the most sought-after families in the stud book.

Consigned by Lane’s End Farm, the colt is rated an “A” by TrueNicks and is from the same immediate family as Saturday’s $2 million Ladies Marathon Invitational Stakes (G3) winner Stellify, by Justify.

The dam is a half-sister to Imagining, by Giant’s Causeway, a millionaire who won the Man o’ War Stakes (G1) and placed in four other grade 1 races.  The dam is also a half-sister to Forestry mare Snooze, the granddam of 2022 Frizette Stakes (G1) winner Chocolate Gelato, by Practical Joke, and stakes-placed Browse, by Medaglia d’Oro, the dam of 2023 Victoria Stakes winner Pipit, by Quality Road.

The colt’s second dam is A.P. Indy mare Daydreaming, a multiple graded stakes winner who is a full sister to Godolphin’s Girolamo, winner of the Vosburgh Stakes (G1), and Dinny Phipps’s homebred Accelerator, winner of the Pilgrim Stakes (G3).  Daydreaming is also full sister to Supercharger, producer of Kentucky Derby (G1) winner Super Saver, and She’s a Winner, the dam of dual classic-placed Bluegrass Cat, by Storm Cat, winner the Haskell Invitational Stakes (G1) and runner-up in the Kentucky Derby (G1), Belmont Stakes (G1), and Travers Stakes (G1).  Daydreaming’s third sibling who is a grade 1-producer is Deputy Minister mare Malka, the dam of Got Lucky, by A.P. Indy, winner of the Spinster Stakes (G1). 

The third dam is Mr. Prospector mare Get Lucky, winner of the Affectionately Handicap (G3) at 4.  Out of Beldame Stakes (G1) winner Dance Number, by Northern Dancer, Get Lucky is a full sibling to champion Rhythm, winner of the Breeders’ Cup Juvenile (G1) and Travers Stakes (G1).

Based on the wild success of Phipps bloodlines at the Saratoga Sale last month and the first day of the Keeneland September Sale on Monday, one can expect more yearlings from Phipps families to fetch impressive prices over the remaining two weeks in Lexington and to achieve success for years to come on the race tracks across the nation.