Flashback: Recalling the Ky. Derby's 7 last-to-first winners

In 2020, Authentic became the first horse in 18 years to win the Kentucky Derby in gate-to-wire fashion, turning back a challenge from heavy favorite Tiz the Law to prevail by 1 1/4 lengths.

Front-running Derby winners might be rare, but they’re far more common than Derby winners who rally from last to first. In 146 editions of the Run for the Roses, only seven horses have managed to charge from the back of the pack to visit the Kentucky Derby winner’s circle.

Let’s take a trip down memory lane and recall these heart-pounding Derby champions:

Macbeth II (1888)

The first Kentucky Derby winner to rally from dead last was Macbeth II, a largely unheralded gelding who gradually worked his way forward to defeat half a dozen rivals in 1888. At the time, the Kentucky Derby was contested over 1 1/2 miles, so Macbeth II had an extra quarter mile to spend reeling in the leaders.

Riley (1890)

Two years after Macbeth II, Riley repeated the last-to-first feat to beat five rivals. Under Hall of Fame jockey Isaac Murphy, Riley trailed during the early stages of the 1 1/2-mile race, but he took command by the end of the opening mile and eventually cruised home 1 3/4 lengths in front over a muddy track.

Pink Star (1907)

Pink Star needed every furlong of the Kentucky Derby’s 1 1/4-mile distance to seal the deal on his last-to-first rally. After trailing five rivals for the first six furlongs, Pink Star began to advance around the far turn but still had two horses to pass in mid-stretch. To the surprise of bettors who disregarded Pink Star’s as the longest shot on the board, the 15-1 underdog never stopped charging, rolling past the leaders to score by two lengths.

Ponder (1949)

Capitalizing on quick early fractions of :22 2/5 and :46 2/5, Ponder took a remarkably straightforward route to victory in the 1949 Kentucky Derby. The Calumet Farm homebred simply stayed outside under jockey Steve Brooks and grinded his way to a three-length victory over future Preakness and Belmont winner Capot, in retrospect denying the latter a Triple Crown sweep.

Gato Del Sol (1982)

One of the least dramatic last-to-first Derby victories came courtesy of Gato Del Sol. The pace of the 1982 Derby wasn’t especially destructive at first glance – :23, :46 1/5, and 1:10 4/5 – but Gato Del Sol nevertheless unleashed a wide, sustained rally down the backstretch and around the far turn to spring a 21-1 surprise. Three other deep closers rounded out the top four.

Ferdinand (1986)

A flawless ground-saving ride from Hall of Fame jockey Bill Shoemaker allowed Ferdinand to ride the rail to a 2 1/4-length victory in the Run for the Roses. The future 1987 Horse of the Year benefited from fast fractions (:22 1/5, :45 1/5, and 1:10 1/5), but remains the most recent horse to win the Kentucky Derby from post 1.

Mine That Bird (2009)

No one who witnessed Mine That Bird’s spectacular victory in the 2009 Kentucky Derby will ever forget it. The unheralded 50-1 long shot trailed the field by a wide margin through reasonable early fractions of :22.98, :47.23, and 1:12.09, then defied all logic to rally up the rail, circle a single rival at the top of the stretch and blast clear to win by 6 3/4 lengths. It’s no surprise that jockey Calvin “Bo-Rail” Borel, widely known for his rail-skimming rides, was the author of this storybook moment under the Twin Spires.

J. Keeler Johnson is a writer, videographer, handicapper, and all-around horse racing enthusiast. A great fan of racing history, he considers Dr. Fager to be the greatest racehorse ever produced in America, but counts Zenyatta as his all-time favorite. You can follow him on Twitter at @J_Keelerman.