Recent Longshot Winners of the Kentucky Derby
Joseph Di Rienzi
The Kentucky Derby which will have its 146th
renewal on September 5 (in this plague year) has been won by some of the
thoroughbred sports’ greatest equines. Citation, Secretariat, Seattle Slew,
Affirmed, Spectacular Bid and American Pharoah [sic] come easily to mind, but part of the Derby’s folklore is that its
annals include some much less distinguished victors who surprised almost
everyone when they garnered the roses at Churchill Downs on the first Saturday
in May. In this piece, I will examine three rank outsiders in the 21st
century who went to postward at odds of at least 50-1 but by the proverbial
racing gods were able to grace the sport’s most hallowed winner’s circle.
Giacomo was a gangly gray son of Holy Bull owned and bred by
Ann and Jerry Moss. He was named after the son of the musician Sting as Jerry
Moss, who with Herb Albert, founded A&M Records, liked to give his horses
names associated with friends in the recording business. Trained by John Shirreffs,
Giacomo began his racing career as a juvenile in July 2004 at Hollywood Park,
finishing fifth beaten almost 11 lengths in a maiden race. With Mike Smith as regular
rider, he found the winner’s circle in his next outing in November at Santa
Anita Park roaring home in front by 10 lengths. After a third place finish in
an allowance race at Hollywood Park, Giacomo was deemed ready for stakes
competition by Shirreffs and entered in the 8½ furlong Hollywood Futurity.
Giacomo belied his nearly 16-1 odds with a powerful closing
rally that found him finishing second a length behind the year’s Two-Year-Old
Champion Declan’s Moon but a nose in front of the Breeders’ Cup Juvenile
winner, Wilko. With this strong performance against the best of his age,
Giacomo became a prime prospect for the 2005 classic races.
Prepping at Santa Anita, Giacomo’s Kentucky Derby stock was
diminished by uninspired performances in the Sham Stakes (he finished third),
the San Felipe Stakes (a distant second) and the Santa Anita Derby (a
non-threatening fourth place finish). Despite these defeats, John Sherriffs and
Mike Smith were satisfied with Giacomo’s progress and believed that the 1¼ mile
distance of the Kentucky Derby would enhance their colt’s chances.
The discussions leading
up to the 131st Kentucky Derby centered on whether Bellamy Road was the next Seattle Slew. The Nick Zito
trained colt had won the W
After the Derby field broke from the gate, there was a rush to the lead with Spanish Chestnut outsprinting the pack. The pace was sizzling for a 1¼ mile race. Down the backstretch, Spanish Chestnut had a 1½ length lead with Flower Alley, High Fly and Bellamy Road right behind. Around the far turn, Flower Alley was the first to drop out, but Bellamy Road and High Fly made concerted efforts to take the lead. Afleet Alex, who was 11th in the early part of the race, made significant progress around the far turn but was caught between horses behind the leading group. Mike Smith settled Giacomo far back in 18th place, hoping to make one final run. At the top of the stretch with the leaders faltering, it appeared anybody’s race to win, when out of the pack 71-1 shot Closing Argument forged to the lead followed on his inside by Afleet Alex who had split horses. Just when it appeared the Derby would be decided between these two, Smith had Giacomo lumbering on the far outside and was able get the big gray colt by the embattled pair near the finish for an improbable ½ length victory. Closing Argument held second by a similar margin over Afleet Alex.
Giacomo winning the 2005 Kentucky Derby
In winning Giacomo became (at the time) the second biggest long shot to win the Derby. The Mosses had previously graced the Churchill Downs’ winner’s circle in 1994 with Kentucky Oaks heroine Sardula (and would achieve even greater fame later with the incomparable Zenyatta). For trainer John Shirreffs, this upset victory was a showcase for the racing world to recognize his training acumen. Mike Smith was recording his first Kentucky Derby victory having previously finished second three times. He saw Giacomo’s victory vindication for his sire Holy Bull, whom Smith rode to an inexplicable 12th place finish in the 1994 Derby.
The Kentucky Derby triumph was the zenith of Giacomo’s racing career. He finished third in the Preakness Stakes and a dull seventh in the Belmont Stakes. In both races, Afleet Alex was the runaway victor, atoning for his Derby defeat. Raced until the end of 2006, Giacomo would win only one other race – the San Diego Handicap before retiring to an indifferent career as a stallion.
An even more unlikely Kentucky Derby hero was Mine That Bird. Owned by Double Eagle Ranch and Buena Suerte Equine, he was a bay gelded son of Belmont Stakes winner Birdstone foaled in 2006 and purchased for $9,500 as a yearling. The smallish Kentucky bred began his racing career in Canada winning several stakes races as a juvenile. However, in his lone United States start, he finished 12th and last in the season ending Breeders’ Cup Juvenile. Preparing for the 2009 classics under new trainer Benny “Chip” Wooley Jr. in New Mexico, Mine That Bird finished second and fourth in minor stakes races at Sunland Park.
Despite his recent modest form, Mine That Bird received notoriety leading up to the Kentucky Derby for two reasons. One was that Chip Wooley, despite being on crutches from a motorcycle accident, personally drove the van carrying the horse the 1,500 mile journey from New Mexico to Kentucky. The second attention getter was that Mine That Bird would be ridden by Calvin Borel who was rapidly becoming a Churchill Downs icon. Despite these factors, the gelding went to post at a generous 50-1 odds.
The year’s Derby was considered wide open with the late scratch of the pre-race favorite I Want Revenge. As the 19 horse field left the starting gate over the sloppy racing surface, there was the usual rush to gain position heading for the clubhouse turn. Borel, in his trade mark move, sent Mine That Bird towards the rail, settling in the rear several lengths behind the 18th place horse. For much of the run down the backstretch, Mine That Bird seemed disconnected from the race apparently languishing in last position. However, as the field moved around the far turn, Borel signaled to his mount who surged along the inside going by horses readily. Around the final bend, Borel steered Mine That Bird off the rail to pass a horse but then put him back on the inside for the stretch run. Powering by the field in mid-stretch, Mine That Bird drew clear for an implausible 6¾ length victory. Finishing second was Pioneer of the Nile, a nose in front of Musket Man.
Mine That Bird winning the 2009 Kentucky Derby
(photo: nytimes.com)
This was one of the truly underdog stories in the history of the Kentucky Derby. In addition to the long van ride, the mediocre races at unheralded Sunland Park and the unknown connections, the sight of Mine That Bird’s trainer, Chip Woolley hobbling on crutches, only increased the mystique. Due praise was given to Calvin Borel who in a little over 24 hours had won the Kentucky Oaks with a “sure thing” in Rachel Alexandra and now took the Derby with a rank longshot.
Mine That Bird continued racing throughout his four-year-old season in 2010. Competing often at the highest level, he was unable to duplicate his Derby victory, retiring after a string of unplacings. Being a gelding, there was no stud career in Mine That Bird’s future. He currently resides at Double Eagle Ranch (the home of one of his owners) in Roswell, NM.
The last of the “upsetters” owes his Derby success more to serendipity than ability. Country House was a chestnut son of Lookin At Lucky bred in Kentucky by Joseph V. Shields Jr. As the result of Shields’ death in 2018 (just after Country House’s first race), ownership in the colt was assumed by Shields’ wife, Maury and his nephew Guinness McFadden. Throughout Country House’s abbreviated racing career he was trained by Bill Mott.
Winless in two starts as a two-year-old in 2018, he broke his maiden in January 2019 at Gulfstream Park in an 8½ furlong race with a powerful come from behind rally. Judged Triple Crown worthy by Mott, Country House was sent to the Fair Grounds Racetrack where he finished second in the Risen Star Stakes and fourth in the Louisiana Derby. In his final Kentucky Derby prep race, the rangy son of Lookin At Lucky placed third to prime Derby contenders Omaha Beach and Improbable in the Arkansas Derby, beaten a total of 6¾ lengths.
The 2019 Kentucky Derby would be one of the most discussed in history with the final chapter still to be written. The first shock was the scratch of pre-race favorite Omaha Beach, a few days before the Derby due to an entrapped epiglottis. In the aftermath, 19 faced the starting gate on a wet day at Churchill Downs. The Bob Baffert triumvirate – Improbable, Roadster and Game Winner were well supported in the betting with the first named the post time favorite. The second choice was Florida Derby winner and former claiming horse Maximum Security.
The field broke cleanly from the starting gate over the
sloppy surface. Jockey Luis Saez put Maximum Security on the lead closely followed by Bodexpress, Long Range Toddy and War of Will. Everything seemed to be
going well as the field went around the far turn. Tyler Gaffalione guided War of Will off the rail to the outside
of Maximum Security as Code of Honor mounted a challenge up the vacated inside.
Also running a strong race was Country House who was rallying on the outside from mid-pack.
As War of Will was looming next to Maximum Security, the latter did not corner
the turn well, forcing the former wide and also impacting Long Range Toddy.
Briefly Code of Honor gained the lead, but Maximum Security fought back and
repelled the latter, War of Will and Country House. At the finish, the son of
New Year’s Day was 1¾ lengths in front of Country House who
was ¾ of a length ahead of Code of Honor. War of Will faded to finish in eighth
place, and Long Range Toddy checked in 17th.
2019 Kentucky Derby with Country House at far left
(photo: nypost.com)
The stewards did not post an inquiry, nor did the rider of presumably
impeded War of Will (Gaffalione). It was Country House’s jockey Flavien Pratt, perhaps sensing an opportunity,
who claimed foul against Maximum Security. After an agonizing 22 minute
wait, the stewards disqualified Maximum Security (the first in Derby history in
the race itself) and placed him 17th. Country House, at odds 65-1
(second longest in Kentucky Derby history), gained the roses, a first for Bill
Mott. The official victor’s owners
(there was an additional partner in LNJ Foxwoods) were understandably jubilant at their
unexpected good fortune. On the other hand, the connections of Maximum Security
were in a state of shock seeing their Derby glory snatched from them by an
administrative decision.
The racing community was divided on the justness of the
stewards’ verdict. Those supporting it argued there was a clear foul and in any
other race there would be no question of a disqualification. The other side
claimed that this was the Kentucky Derby and only an egregious interference
should merit an alteration in the order of finish. They boosted their argument
claiming Country House, the chief beneficiary of the
stewards’ decision, was unaffected by Maximum Security’s wayward behavior around the
stretch turn and should not be rewarded with the victory. Gary West and his wife Mary, owners of Maximum Security,
convinced of this argument, appealed the disqualification to the Kentucky Horse
Racing Commission. When denied, the Wests and their attorneys took the case to
a federal district court. When informed by the judge that decisions by the
Commission are not subject to judicial review, the connections of Maximum
Security have made a further appeal, which is still pending in the U. S. Court
of Appeals.
The other two horses (Giacomo and Mine That Bird) discussed
above had a combined record of 1 win in 18 starts subsequent to their
respective Kentucky Derby surprise victories. Country House was not able to
improve that dismal record for he never raced again due to a series of ailments
and injuries. Retired in early 2020, it was just recently announced he will
stand stud in 2021 at Darby Dan Farm in Lexington, KY.
So we see that these
three thoroughbreds were dismissed before the Kentucky Derby and, by in large,
drifted into obscurity after, but on that first Saturday in May, they shone
brightly in the Kentucky sun.
