How a Great Depression bankruptcy created America’s prettiest racetrack in Kentucky

Jack Keene’s Depression-Era Dreams Built Modern Keeneland

The Keene family saga began with a gift of 6,000 Kentucky acres from Governor Patrick Henry in 1790. John Keen built Keene Place in 1805 and started a horse racing tradition that ran through generations.

In 1825, the Marquis de Lafayette even spent a night at the estate. Later, John’s great-great grandson Jack had big dreams.

He laid out a racetrack by hand in 1916 and spent two decades building a grand limestone barn with no blueprint. But the Great Depression crushed him.

In 1935, broke and beaten, Jack sold his half-finished vision for $130,000.

Today, Keeneland Race Course stands as one of America’s most beautiful tracks, where Jack’s dream lives on in stone and turf.

Governor Patrick Henry Gave a Revolutionary Soldier Kentucky Land

In 1790, Virginia governor Patrick Henry gave 6,000 acres of Kentucky Bluegrass land to John Keen for his Revolutionary War service.

The land sat in Fayette County, which was still part of Virginia before Kentucky became a state. John Keen moved his family from their Fauquier County, Virginia home to start fresh on this new land.

His land grant would later become home to one of America’s favorite racetracks.

The Keenes Built Their Family Home in 1805

John Keen and his wife Mary (called Polly) built a strong brick home on their land in 1805. They named it Keene Place, adding an extra “e” to their last name along the way.

The house turned into a family legacy that six generations of Keenes lived in for nearly 150 years.

The family set up a private cemetery behind the main house where they buried family members, creating a lasting tie to the land.

Lafayette Stayed at Keene Place During His American Tour

On May 15, 1825, the Keene family hosted Marquis de Lafayette, the last living Revolutionary War major general. Lafayette stayed overnight at Major John Keene’s home during his goodbye tour across America.

He and John Keene had fought together during the Revolutionary War. The general’s military guards camped on the grounds that later became the famous racetrack.

Local history books list this visit as one of early Lexington’s biggest events.

Horse Breeding Ran in the Family for Generations

John Keene started breeding Thoroughbreds at the start of the 1800s, becoming one of the first horsemen in the Bluegrass region.

His family land quickly became known as Kentucky began to stand out as the perfect place to raise racehorses. The horse breeding tradition continued with each new generation of Keenes taking over.

Throughout the 1800s, the Keene name grew more respected in racing circles across the country.

Jack Keene Took His Horse Skills Around the World

John Oliver “Jack” Keene, born in 1870 as the original John Keen’s great-great grandson, grew up with horses all around him.

He started working at Lexington’s Kentucky Association track, learning everything about horse racing. His skills soon took him to Chicago and then California, where he met a rich owner named Jimmy Fletcher.

This friendship changed Jack’s life, as Fletcher’s growing international racing business soon had Jack traveling across the Pacific.

Racing Success Took Jack from Japan to Snowy Russia

Jack Keene traveled with Fletcher’s racing business to both Japan and Russia.

The cold Russian winters taught Jack how to train horses in tough weather, giving him the idea to build an indoor training track back home. His time overseas showed him different building styles and training methods.

Jack paid close attention to how Russians worked with limestone, which later shaped the stone buildings at Keeneland.

A Dream of Building His Own Track Brought Jack Home

Jack Keene came back to the United States and his family’s Keeneland Stud with new ideas. The old Kentucky Association track had fallen apart, so Jack wanted to build his own racetrack.

In 1916, he started building on family land, planning a private club where friends could train and race horses.

Jack worked without blueprints, creating a mile-and-one-sixteenth oval track with west-facing stands so morning viewers would have the sun at their backs.

Money Problems Slowed Jack’s Big Construction Plans

Jack never had much money, so building moved forward slowly over twenty years.

He paid for the project with gambling winnings and horse sales, causing long delays whenever he ran out of cash.

All buildings used limestone dug right from the Keene farm, cut by local workers using methods Jack saw in Russia.

Even after spending over $400,000 on his dream track, by 1935 less than half of what Jack planned was finished.

The Great Depression Ended Jack’s Racing Dreams

The Great Depression finally forced Jack Keene to give up on his racing plans.

On August 29, 1935, Jack sold his limestone barn, track, and 148 acres for $130,000 to Hal Price Headley’s newly formed Keeneland Association.

This group of forward-thinking horsemen came together after the old Kentucky Association track closed in 1933.

They needed a new place for Lexington racing, and Jack’s partly built facility offered the perfect starting point for their plans.

New Owners Finished Jack’s Track in Record Time

The Keeneland Association moved quickly after buying Jack’s property in 1935. They started fast construction, using his limestone buildings as the core of their bigger facility.

The new owners kept Jack’s unique design while adding modern betting equipment and comfortable areas for viewers.

Workers rushed to finish construction before the planned first races in October 1936, turning Jack’s dream into a working racetrack.

Opening Day Proved Jack’s Vision Was Worth the Wait

Keeneland Race Course welcomed 8,000 excited fans on opening day, October 15, 1936.

A talented filly named Myrtlewood won the six-furlong Keen Handicap, a race specially named to honor the family whose land made it all possible.

Jack Keene watched from the stands as horses thundered around the track he had laid out decades earlier.

Though ownership had changed hands, the track bearing his family name went on to become one of America’s most treasured racing venues and Thoroughbred auction houses.

Visiting Keeneland Race Course, Kentucky

You can explore Keeneland Race Course at 4201 Versailles Road in Lexington for free when races aren’t happening.

Take guided tours covering the paddock, grandstand, and 80 years of history, or visit the Keeneland Library weekdays from 8:30 a.m. to 4:30 p. m.

Look for the historic Keene Place mansion where Lafayette stayed in 1825. During race meets, general admission costs $7 on weekdays and $10 on weekends.

This article was created with AI assistance and human editing.

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