Crystal Quest made headlines in March, defeating stablemate and fellow Live Oak entrant Forever Souper in winning the Turf Classic Stakes at Tampa Bay Downs on Florida Cup Day. The determined score gave Live Oak its 12^th Florida Cup Day winner. It was the second stakes victory for Crystal Quest, who won the 2024 Florida Cup Sophomore Turf Stakes at the Oldsmar track. Crystal Quest is a Live Oak-bred son of Uncle Mo out of Giant Crystal, by Giant’s Causeway, and is trained by Michael Trombetta.

On August 4th, Live Oak Plantation’s homebred, Bring Theband Home earned his first graded stakes win Sunday at Saratoga with a front-running score in the $300,000 Troy S. (G2). He came home a 1 ½-length winner in 1:00.38 for the 5 ½-furlongs on the firm turf, missing the track record by less than a half-second.

In a memorable day of racing for Live Oak, Win for the Money and And One More Time provided Live Oak Plantation with a pair of Grade 1 wins at Woodbine on Sept. 14. Win for the Money captured the $1 million Woodbine Mile and just a few hours later, Live Oak’s And One More Time won the Natalma Stakes (G1).

Win for the Money is a son of Mohaymen acquired by Live Oak Plantation for $350,000 out of the 2021 Fasig-Tipton Florida Sale of 2-Year-Olds in Training. And One More Time is a daughter of Omaha Beach purchased by Live Oak for $750,000 at the 2023 Fasig-Tipton Saratoga Select Yearling Sale. Mark Casse conditions both horses.

Live Oak Plantation’s Ticker Tape Home had to wait patiently for running room on the far turn of the Seaway Stakes (G3) at Woodbine on Aug. 24, but once the daughter of Medaglia d’Oro found daylight, she drove to the front to record her first graded stakes victory.

Trained by Mark Casse, Ticker Tape Home won the Fury Stakes at Woodbine in 2023. Bred in Ontario, Ticker Tape Home is out of the War Front mare Journey Home, a graded stakes winner and multiple graded stakes-placed runner. Ticker Tape Home was a $625,000 purchase at the 2021 Fasig-Tipton New York Saratoga Select Yearling Sale.

Our Flash Drive was among Live Oak Plantation’s standouts in 2023. The homebred daughter of Ghostzapper cruised to a facile victory in the Whimsical S. (G3) in May at Woodbine in her first start since annexing the Bessarabian S. (G2) in November of 2022. She went on to win the Royal North S. (G2) in her next start, making it three consecutive graded stakes wins for the Mark Casse trainee. Our Flash Drive is produced from the unraced Dynaformer mare Dynamotor.

Our Flash Drive turned in the best performance of her career in the $175,000 Bessarabian S. (G2) on Nov. 12 at Woodbine, rolling to a 5 ¾-length win to give the Live Oak Plantation homebred her third career stakes win.

Entering the stretch, she swept past the leaders easily and pulled away with complete authority to finish the seven furlongs in 1:20.76, less than a second off the track record, to earn a career-best Beyer Speed Figure of 99. Our Flash Drive won both the Selene S. (G3) and Ontario Colleen S. (G3) in 2021.

In April, Live Oak Plantation was named the 2021 Outstanding Owner at the 47th Annual Sovereign Awards ceremony, hosted by The Jockey Club of Canada. Live Oak won its first owner Sovereign Award in 2020, and followed that year up with even better results in 2021. The stable had 19 Canadian winners, with seven seconds and four thirds, from 68 starters. Stable earnings topped $1.4 million, including seven stakes wins.

The stable’s top performer was Our Flash Drive, trained by Mark Casse, who won the Selene S. (G3) on Tapeta and the Ontario Colleen S. (G2) on the turf.

Homebred Souper Stonehenge won the Vigil S. (G3) and Jacques Cartier S. (G3), while another homebred, Souper Escape, took the Trillium S. (G3), and a third produce from the farm, Tap It to Win, defeated eventual 2021 Horse of the Year Mighty Heart in the Seagram Cup (G3).

Live Oak Plantation earned two Sovereign Awards for its achievements in 2020. The farm itself won the award for Outstanding Owner, while the farm’s homebred 4-year-old filly Souper Escape was named Champion Older Main Track Female.

Live Oak finished 2020 with more than $1.1 million in Canadian earnings and five stakes wins. In addition to Souper Escape, the farm’s March to the Arch won the King Edward S. (G2), Salute With Honor won the Durham Cup (G3), and the 2-year-old filly Souper Sensational took the Glorious Song S. Overall, Live Oak won or placed in 57 percent of its starts.

Souper Escape, trained by Michael Trombetta, took divisional honors on the strength of a pair of graded stakes victories: the Seaway S. (G3) and the Trillium S. (G3). The daughter of Medaglia d’Oro also placed in a pair of listed stakes and earned over $200,000 for the year. Souper Escape is out of Oak Leaf S. (G1) winner Cry and Catch Me.

Also in 2020, Florida-bred Win Win Win became Live Oak Plantation’s newest Grade 1 winner at Saratoga with one of the most incredible stretch runs to take the Forego S. (G1) by a half-length in a driving rainstorm.

Win Win Win dropped some 18 lengths off the early pace as he trailed the field of 11 through a half-mile. The 4-year-old colt began to make up ground on the turn but traveled eight-wide coming into the stretch. Still about six lengths from the front with a furlong to run, Win Win Win was in full flight on the outside and came rolling to hit the wire in 1:21.71 for the seven furlongs on a sloppy track.

“What an amazing horse,” said winning rider Javier Castellano. “I’m truly honored to ride the horse and very blessed with the way everything went.”

Live Oak Plantation’s flashy homebred 3-year-old colt Win Win Win turned in a dynamic performance in the $125,000 Pasco S. at Tampa Bay Downs, drawing off to score by 7 1/4 lengths in 1:20.89 for the seven furlongs, breaking the track record by nearly a half-second.

The nearly black colt, who is trained by Michael Trombetta, has now won three of four starts for his connections, with earnings of $127,300.

Live Oak had a banner year in 2017. Once again, World Approval, now 5, was the stable star, with 5 stakes wins, including 3 Grade 1s –  the $2,000,000 Breeders’ Cup Mile (G1), the $800,000 Woodbine Mile S. (G1), and the $500,000 Fourstardave H. (G1). Live Oak enjoyed a graded stakes double at Keeneland on April 8 when Holding Gold won the $200,000 Shakertown S. (G2) and Awesome Slew added the $250,000 Commonwealth S. (G3) to his resume. Awesome Slew also won the Ack Ack S. (G3) and was placed in the $1,000,000 Breeders’ Cup Dirt Mile (G1) and the $600,000 Forego S. (G1).  World Approval and Awesome Slew also surpassed the $1 million mark in progeny earnings, joining Miesque’s Approval, Za Approval, and Revved Up in that exclusive club. At Woodbine, Souper Tapit became a graded stakes winner for the first time in the $125,000 Marine S. (G3). The homebred 3-year-old colt is out of Live Oak’s Grade 1-winning mare Zo Impressive.

In the first half of 2018, Live Oak has seen the return of superstar World Approval winning the Tampa Bay S. (G3) in his 6-year-old debut, bringing his earnings to over $3,000,000. Awesome Slew is poised to have another great season, finishing runner-up in the Carter H. (G1). Let It Ride Mom became the newest Graded stakes winner, taking the Whimsical S. (G3) at Woodbine in her 4-year-old debut.

In 2016, World Approval continued to add to his illustrious resume with a victory in the historic $300,000 United Nations S. (G1) at Monmouth Park. Another Live Oak homebred, the 2-year-old filly Victory to Victory, would taste Grade 1 success in Woodbine’s Natalma S. Victory to Victory’s dam Points of Grace was the 2009 Canadian Champion Turf Female. Golden Hawk also was a graded winner at Woodbine, taking the Grey S. (G3) for 2-year-old colts. Golden Hawk, also a Live Oak homebred, is out of Gone Purrfect, whose siblings include champion sprinter and leading sire Speightstown and a top 3-year-old of 2017 in Irap. Awesome Slew earned his first stakes success in the $300,000 Smart Jones S. (G3) at Parx in a sign of good things to come for the 3-year-old colt. Live Oak wrapped up 2016 with 226 runners finishing in the top 3 in nearly 50% time, with earnings of more than $2.3 million

2015 saw the explosion of World Approval onto the scene in the male turf division. The 3-year-old, a younger sibling to Za Approval, started his impressive season with a win in the Sophomore Turf S. at Tampa Bay Downs, then stepped up his game to take the American Derby (G3) at Arlington Park. The best was yet to come in the Saranac S. (G3) at Saratoga, where the gray set a 1 1/8-mile track record in 1:45.39. Veteran Florida Won continued to turn in top efforts, winning the Seagram Cup (G3) at Woodbine and travelling to Pennsylvania to take the $200,000 Presque Isle Mile. Souper Colossal also bagged another score in the Texas Glitter S. at Gulfstream, while Under Control won the $100,000 Lure S. at Saratoga. With 234 starters during the year, Live Oak’s runners finished in the top 3 exactly 50% of the time, including 42 victories.

Homebred Za Approval proved to be the stable star in 2013, winning a trio of Grade 3 races: Appleton H., Red Bank S., and the Knickerbocker S. The then 5-year-old Za Approval is out of the top-class broodmare Win Approval and is a brother to millionaires Miesque’s Approval and Revved Up. Other stakes winners during 2013 included homebred Souper Speedy, who took the Jaipur S. (G3) at Belmont Park. Souper Speedy is a half-brother to Brilliant Speed.

Live Oak’s Successful Song kicked off 2013 with a win in her final start before retirement, taking the $300,000 Florida Sunshine Millions Distaff. Another homebred, Successful Song retired with $597,538 in earnings.

In 2014, Za Approval notched another stakes victory in the $100,000 Real Courage S. at Belmont Park, and was but one of several notable Live Oak performers during the year. Two-year-old Souper Colossal made a splash in the juvenile male division with scores in the Tyro S. and Sapling S. during the summer, and Florida Won took the Ontario Derby (G3) in early Autumn.

In 2010, the Live Oak charge featured two-time Grade 2-winning juvenile To Honor and Serve, an Eclipse Award finalist for Champion 2-Year-Old Male. In 2011, Live Oak was led by its eighth and ninth Grade 1 winners – leading 3-year-olds To Honor and Serve and Brilliant Speed. To Honor and Serve captured his first Grade 1 triumph over older horses in the Cigar Mile (G1) to close out the season, while Brilliant Speed earned a berth into the Kentucky Derby with a win in the prestigious Blue Grass S. (G1) at Keeneland earlier in the year.

Homebred Zo Impressive joined To Honor and Serve and Brilliant Speed as stable stars in 2012 when she captured the Mother Goose S. (G1) at Belmont. To Honor and Serve went on to stud and now represent Live Oak as one of the more promising young sires of the decade.

Since 2005, Live Oak Plantation enjoyed banner years with its racing operation. Live Oak, which witnessed homebred Laser Light finish runner-up in the 1982 Kentucky Derby, got back to the world’s biggest race in 2005 with the top 3-year-old homebred High Fly, winner of the Florida Derby (G1) and Fountain of Youth (G2). Live Oak was also represented in that year’s Kentucky Oaks by Grade 1 winner In the Gold, who finished second.

The momentum carried over into 2006 where the success reached another level, with eight Live Oak Plantation stalwarts winning a total of 13 graded races. Leading the way was Miesque’s Approval, a homebred who enjoyed a storybook turnaround at the age of seven to win the Breeders’ Cup Mile (G1) and an Eclipse Award for best male turf performer. The Breeders’ Cup win was the first for Live Oak Plantation and it was delivered by a homebred that embodied the hard work, patience and perseverance upon which the racing operation has built its success. Live Oak Plantation closed out 2006 with 52 stakes horses and over $5 million in earnings.

A perennial leading owner in North America, Live Oak Plantation has had several top-class performers over the years that have won many of North America’s biggest races, including over 30 graded stakes winners of more than 50 graded stakes. Sultry Song and Solar Splendor were brothers who enjoyed immense success in the early 90s. The siblings, out of the Live Oak Stud foundation mare Sultry Sun, captured Grade 1s on the same card at Belmont Park in 1992 and retired as equine millionaires.

An important part of Live Oak Plantation is the network of trainers, and Live Oak employs several of North America’s top conditioners including: Mark Casse, and Michael Trombetta.

Charlotte C. Weber bought the farm in 1968 to build a breeding program that has grown into a massive success over the last 50 years.