Kentucky Derby 2011: 5 Longest Shots to Win Greatest 2 Minutes in Sports

Favorites rarely win the Kentucky Derby but you already knew that because as of tomorrow, everyone in the USA is a horse handicapper.

There have been some favorites over the years, the 1970 produced a slew of them, and no pun intended. Here are few that some of us older handicappers remember.

The following horses were all post time favorites that went on to win the greatest two minutes in sports: Riva Ridge, ’72; Secretariat, ’73; Cannonade, ’74; Foolish Pleasure, ’75; Seattle Slew, ’77; and Spectacular Bid, ’79. Surprisingly, Affirmed, the last Triple Crown winner in ’78, was not favored at Louisville.

Over the past three decades, only four favorites have triumphed, all since 2000, they include Big Brown, ’08; Street Sense, ’07; Smarty Jones, ’04; and Fusaichi Pegasus, ’00.

Did you know that three of the longest shots to ever win the Derby have done so in the past 12 years? Keep in mind, this race is 137 years old tomorrow.

So sit back, click through history, and learn a little about the five longest shots to conquer Churchill Downs on the first Saturday in May.

No.5: Charismatic, 1999, 31 to 1

Charismatic was a third-generation descendant of both Secretariat and Northern Dancer and he began racing as a two year old in claiming races.

In fact, he ran in a claiming race just three months prior to the Derby.

Trained by D. Wayne Lukas and ridden by 1991 Kentucky Derby winning jockey Chris Antley, Charismatic took the lead away from Lukas’s other entry, stable mate Cat Thief inside the eighth pole and held off the 5-2 favorite Menifee, to win the 125th run for the roses.

Trainer Bob Baffert had three morning line favorites entered in hopes of winning his third Derby in a row. It was not to be, as the week belonged to Lukas.

D. Wayne was inducted into the Horse Racing Hall of Fame that Tuesday before the Derby.

Baffert's entries of General Challenge and Excellent Meeting finished 11th and fifth respectively, while Prime Timber finished third.

Charismatic broke from the gate out front for a brief time but settled into eighth and stayed there until the run before the final turn.

He moved to fifth entering the final turn and by the time he was exiting the turn, he was third and driving.

Menifee was way back on the backstretch but also moved into contention on the turn and joined the battle as the second largest crowd (151,051) in Derby history went nuts.

At the head of the stretch, the winner was third on the outside, with his stable mate Cat Thief on the rail. Worldly Manner was in between but beginning to fade as Menifee was charging hard and closing fast.

Charismatic then took the lead away from Cat Thief inside the eighth pole and started the duel of holding off Menifee.

Charismatic crossed the finish line in 2:03:29, holding off the charging Menifee by a neck. He paid a whopping $64.60 to win and the two dollar exacta of 11 & 13 paid $727.80 in Louisville.

The win was especially pleasing for jockey Chris Antley, who just the year before, was out of racing battling drug addiction and weight problems.

Antley eventually passed away because of his drug addiction. In 2000, he was found dead on the floor of his California home.

Originally ruled a homicide due to the nature of the head trauma Antley sustained, it was later determined the trauma was cause because of a fall from a drug overdose.

Antley would ride Charismatic to victory in the 124th Preakness Stakes in Baltimore but his quest for the elusive Triple Crown fell short when Charismatic broke his leg in two places on his run down the backstretch at the Belmont Stakes.

Charismatic still finished third in the race after injuring his leg in the stretch run. Antley jumped off the horse after the finish line and attempted to hold the horse's leg in place while the horse limped.

The horse recovered following surgery and the moment was voted was selected by racing fans as the 1999 National Thoroughbred Racing Association Moment of the Year.

Charismatic finished his career with five wins, two places, and four shows in 17 career starts, for total earnings of $2,038,064. He won the Eclipse Awards for 3-year-old Colt of the Year and Overall Horse of the Year for 1999.

In 2002, Charismatic was shipped to Japan to stand at stud

No. 4 Gallhadion, 1940, 36 to 1

A horse named Gallhadion pulled the biggest Kentucky Derby upset since 1913.

In the 1940 race, Gallhadion was a 36-1 post time longshot to the favorite, Bimelich, who went off at even money.

Owned by Ethel V Mars of Milky Way Farms (are you putting this together yet), so named for her company's famous candy bars.

Gallhadion paid $72.40 to win.

The horse would not have much success following the Derby as he finished third in Baltimore at the Preakness and out of the money at the Belmont.

No.3 Giacomo, 2005, 50 to 1

How big was this upset, consider that the only time you heard the name Giacomo called before the final stretch run was to say that he was 17th and leading the last of the 20-horse field. 

Giacomo, a 50-1 longshot was ridden by Mike Smith and trained by John Shirreffs. Smith, who has won all three Triple Crown races and just about every other race in North America worth winning, also rode Giacomo's sire, the great-- Holy Bull.

Holly Bull was the 1994 Eclipse Award Winner as horse of the year.

Giacomo was part of a full 20 horse filed as the second largest crowd to ever see the Kentucky Derby to date was on hand at Church Hill Downs. 

Wood Memorial winner Bellamy Road was the 5-2 post time favorite over 9-2 second choice Afleet Alex.

The speed horses in the race, Spanish Chestnut and Going Wild, both longshots, went to the front as expected.

On a beautiful sunny day in Louisville with a super fast racing surface, Spanish Chestnut recorded the second fastest pace in Derby history.

However, Spanish Chestnut as a 79-1 shot, was to set the race up for third choice Bandini, also owned by Michael Tabor

The strategy backfired as Bandini simply never got going and finished nineteenth. The super fast pace also took a tole on the favorite, Bellamy Road.

The favorite tired at the top of the stretch and faded to finish seventh. Turning for home, 7-1 shot High Fly who was getting a nice trip and sitting in fourth down the backstretch inherited the lead.

Like many young horses, he could not push forward and finished tenth.

Afleet Alex and another big longshot Closing Argument (72-1) looked to be headed to the finish line together until Mike Smith pulled out his whip. 

With less than a furlong to go, Giacomo, who had raced in 18th place down the backstretch and was briefly trapped behind a wall of horses at the 5/16 pole, got out and took off down the middle of the track.

Smith continued to whip and Giacomo continued to run as he pulled off the upset victory by half-a-length over Closing Argument in 2:02.75.

Giacomo paid a whopping $102.60 to win and the two-dollar exacta of 10 & 18 with both longshots paid $9,814.80. The two-dollar triple paid $133,134.80. Closing Argument paid $70.00 for a two-dollar bet to place.

If you were good enough to pick the superfecta that day at Churchill, you left rich. 10, 18, 12, & 7 paid $864,253.20.

Giacomo finished third in the 2005 Preakness Stakes behind the favorite Afleet Alex.

He finished seventh in the 2005 Belmont Stakes, again behind the favored Afleet Alex; Smith said after the race that the horse had breathing problems.

No.2 Mine That Bird, 2009, 51 to 1

This one still makes me sick. I was told to put this horse in an exacta by my father and simply threw it out. I cashed a ticket across the board for Ice Box.

The '09 Derby favorite, I want Revenge, never made it to race day, as trainer Jeff Mullins discovered a hot spot on the horse's left front ankle.

With a wet track expected, Mullins and owner David Lanzman did not want to take any chances, scratching the horse.

A field of 19 three-year-olds went to post but Because of overnight rains, the track was rated sloppy for the Derby.

Friesan Fire, winner of the LeComte, Risen Star, and Louisiana Derby, was the 7-2 post time favorite for trainer Larry Jones. Dunkirk, trained by Todd Pletcher was the 5-1 second choice.

At the start, longshot Join in the Dance bumped Mine That Bird and like most longshot speed horses in the Derby, went to the lead over the sloppy track. Jockey Garrett Gomez kept Pioneer of the Nile up close to the pace in third.

Favorite Friesan Fire was stuck in traffic at seventh. Veteran Edgar Prado settled Dunkirk, who stumbled badly at the start, into tenth.

Entering the stretch, Join in the Dance continued to lead through a mile in 1:37.49 but like all longshot field setters, tired and eventually finished seventh.

Pioneer of the Nile briefly inherited the lead at the 3/16 pole, but this was short lived.

Calvin Borel, who won the Derby in 2007, was aboard Mine That Bird. The second-longest shot on the board at 50-1, sat in last for the first six furlongs saving ground the whole way. Bird was as far back as 21 lengths.

However, on the turn, and with ease, the longshot began to pick off horses one-by-one.

So easy and smooth was Borel that if you listen to race on the video above, the race announcer on NBC does not even notice the move Borel made with Bird.

In fact, he missed it completely and in my opinion delivered the worst call of a Kentucky Derby ever on network television.

Borel continued passing on the inside until he found a narrow opening between Join in the Dance and the rail and took off to take the lead.

Mine That Bird would never be challenged continuing to pull away and the second biggest longshot in Derby history, won by 6 3/4 lengths over Pioneer of the Nile in a time of 2:02.66.

The winning payoff of $103.20 is the second highest in Derby history.

The day after his Derby win, Mine That Bird's connections were uncertain if they would come back two weeks later and try for the Preakness Stakes. They planned to wait and assess the horse's condition first.

It was announced on May 4, 2009, on ESPN that Mine That Bird would run in the Preakness.

In a twist straight from the popular book, Men are From Mars and Women are from Venus, Borel opted to ride the filly, Rachel Alexandra, which was his regular mount.

In the Preakness, Rachel Alexandra, who had won the Kentucky Oaks by 20 lengths with Borel aboard, was the favorite.

Mine That Bird was ridden by Mike Smith and finished in second place, a length behind Rachel Alexandra.

Mine That Bird ran in the Belmont Stakes on June 6, 2009, where Calvin Borel once again rode him. After starting last, he began moving up along the backside.

After taking the lead at the top of the stretch, he battled with Dunkirk and Charitable Man down the lane but was beaten by Summer Bird and Dunkirk to finish third.

Borel would go onto win last year’s Derby, his third in four years, aboard 8-1 shot, Super Saver.

No.1 Donerail, 1913, 91 to 1

If you remember Roscoe Goose and T.P Hayes, then I want to know what your secret is.

The jockey and trainer of the longest shot to ever win the Kentucky Derby must have been happy men that day.

The 91-to-1 shot, paid $184.90 to win and $41.20 to show.

In the 39 running of the roses, many of the horses in the small field led the race.

As the horses began towards the stretch, a horse named Ten Point was winning but at that point, Donerail made his move.

He came from behind and, at high speed and captured the lead. Other horses pursued him, but they could not catch him. When he crossed the wire, he was half a body length ahead of Ten Point.

Out of 62 starts, Donerail won 10, placed in 11, showed in another 10 with career earnings of, and get this, $15,156.

The average wage in 1913 was $1,296.00. If you were lucky enough to have picked the winner in the eight-horse field, then you just netted 15 percent of your yearly income.

In today’s world, you would have to have a pretty good day at the track to hit 15 percent of the average yearly wage in 2010.

In 2010, Derby winner Super Saver allowed his owner to pocket a cool $1,425,200. Back in 1913, the winner received a purse of $5.475.

Wow what a difference 98 years makes.

In 1913, you could have taken your Derby winnings and almost have paid for half of a new car.

They averaged just $490.00 and you could have filled the vehicle up almost 90 times depending on the size of the gas tank.

Since no video of the race exists and who wants to look at a black and white winners circle photo anyway, Enjoy Secretarait's 1973 Derby Triumph.