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Overlay players, who’re always shopping for value, and contrarians, who refuse to back popular choices in anything, love the Kentucky Derby. It’s Payday.

For 20 years now, the Derby has confounded the chalk players and played into the hands of the contrarians and overlay bettors. Not since 1979, when Spectacular Bid won the roses, has a favorite crossed the finish line first. Instead, in many instances, a horse that ran second, third or even fourth in a major prep has triumphed on the first Saturday in May.

A good case can be made for joining the Derby overlay or contrarian camps. They figure that anything can happen in the Derby, and it usually does. For example:

• Charismatic, a colt that had raced in a $62,500 claiming event only months before, won the 1999 Derby and paid a whopping $64.60.

• Go for Gin, who had gone to the post three times as a two-year-old before breaking his maiden, walloped highly acclaimed Holy Bull in the 1994 Derby and returned $20.20; the Bull finishing an ignominious third from last.

• Lil E. Tee, who finished second in the Arkansas Derby and had won only $29,106 as a two-year-old, defeated Arazi, acclaimed by some as "horse of the century," in the 1992 Derby, rewarding backers with a hefty $35.60 payoff.

• Ferdinand, racing in the shadow of favorite Snow Chief’s reputation, advanced from last at the half-mile marker to capture the 1986 Derby, paying a handsome $37.40 and giving Bill Shoemaker his fourth and final Derby win.

• Genuine Risk, a chestnut filly, seriously embarrassed the guys when she captured the 1980 Derby, paying a respectable $28.60.

Nice payoffs, huh? And not all that unusual in the span from 1980 to 1999 when 15 double-digit win mutuels were recorded, averaging $27.80.

Double-Digit Derby Payoffs
1980 to 1999

Genuine Risk 1980 $28.60
Gato Del Sol 1982 $44.40
Spend a Buck 1985 $10.20
Ferdinand 1986 $37.40
Alysheba 1987 $18.80
unbridled 1990 $23.60
Strike the Gold 1991 $11.60
Lil E. Tee 1992 $35.60
Sea Hero 1993 $27.80
Go for Gin 1994 $20.20
Thunder Gulch 1995 $51.00
Grindstone 1996 $13.80
Silver Charm 1997 $10.00
Real Quiet 1998 $18.80
Charismatic 1999 $64.60
Average: $27.80
Heavy betting on the two or three top choices in the Derby nearly always results in inflated prices on the other entrants in the Derby field. The sharper contrarians look for odds of 5-1 or up on horses with a legitimate shot to win the Derby. Some contrarians even bet multiple horses, if the odds are attractive enough. This is sometimes called shotgun handicapping.

The bottom line is that contrarians bet against the favorite, and that has worked for 20 straight years. Will it work again in Derby 126? Maybe. But it’s not enough just to eliminate the favorite. You have to find the winner.

A solid approach is to carefully review the past performances of the top four finishers in each of the six major Kentucky Derby preps.

Nineteen, or 95%, of the past 20 winners of the Derby finished in the top four positions in one or more of the six key Derby prep races, which are Gulfstream’s Florida Derby (G1), the Santa Anita Derby (G1), Oaklawn’s Arkansas Derby (G2), Aqueduct’s Wood Memorial (G2), Keeneland’s Blue Grass Stakes (G1) and Turfway’s Spiral Stakes (G2) (formerly the Jim Beam).

While nine, or 45%, of the Derby winners since 1980 had won one or more of these major preps, eight, or 40%, had finished either second or third. Two, or 10%, had finished fourth. Only one Derby winner in the 20-year span from 1980 to 1999 did not earn a key Derby-prep credit — Spend a Buck (1985).

Another Grade II race, the Louisiana Derby, with a purse of $750,000, may become a key Derby prep. Its winner in 1996, Grindstone, went on to capture the Kentucky Derby.

Such stats prove the ancient axiom that class wins the big races. Yet, class is a somewhat elusive quality. So many times, three-year-olds change form dramatically in the weeks and months leading up to the Derby, and their true class is hard to identify.

A prime example is Charismatic, winner of the 1999 Derby, who established his class rather late. In his races at Santa Anita during January of 1999, Charismatic didn’t show much, finishing off the board. But after winning a $62,500 claiming race at Santa Anita in February — on a disqualification — the colt began to exhibit his true class. In his next trip, he finished second in a $50,000 allowance race at Santa Anita and followed that with a close second in the El Camino Real Derby (G3) at Bay Meadows. Next, at 44-1, he finished fourth in the Santa Anita Derby. Clearly, he was ascending the class ladder.

Trainer D. Wayne Lukas shipped him to Kentucky, where he easily won the Lexington Stakes (G2) at Keeneland in record-shattering time for the mile and one-sixteenth. Two weeks later, he went three-wide to capture the Kentucky Derby.

Ironically, many handicappers still considered him too cheap, even after his impressive Lexington Stakes win, to be a serious Derby contender. He went to post at odds of 31-1.

The following angles are useful in arriving at major players in the Derby line-up.

• Look for a horse that closed sharply in his or her last race, even though maybe finishing third or fourth. Such horses, aptly labeled "now" horses by D. Wayne Lukas, may be ready to peak on the first Saturday in May.

The late Jim Bolus, Kentucky Derby historian and ace handicapper of the event, always looked closely at classy, late-developing Thoroughbreds as patented upsetters in the Run for the Roses. He considered the Blue Grass Stakes a particularly important prep race because of its class and closeness to the Derby. Bolus picked longshot Sea Hero to win the 1993 Derby based on his pedigree and the colt’s strong late move to finish fourth in the Blue Grass Stakes.

• Pay particularly close attention to the entrants of trainers who’ve won the Derby or have Derby experience, including four-time winner D. Wayne Lukas and two-time winner Bob Baffert. This year, Lukas is again planning a multiple-entry in the Derby. Despite his filly Surfside’s less-than-spectacular win in the Santa Anita Oaks in which she clocked a so-so 1:44.03 for the mile and one-sixteenth and barely held off a filly who’d broken her maiden in her last race, Lukas remained high on the daughter of Seattle Slew. She raced without Lasix in the Oaks. He was pointing her toward the Santa Anita Derby against an all-male cast. Her performance in that race will provide a true index to her Kentucky Derby potential. The Lukas party also includes High Yield, who dueled Hal’s Hope to the wire in the Florida Derby, losing by only a head; Exchange Rate, winner of the $125,000 Risen Star; and Commendable, fourth a length behind winner War Chant in the San Rafael but off the board after setting the pace in the Grade II San Felipe at Santa Anita.

Baffert’s top gun for the Derby is Captain Steve, a fast-closing third in the Louisiana Derby. Last year, Captain Steve won Keeneland’s Gr. II Lane’s End Breeders’ Futurity, Churchill’s Kentucky Jockey Club and the Grade I Hollywood Futurity. Another Baffert contender may be the $1.8 million Tribunal, second to Fusaichi Pegasus in a distance allowance race at Santa Anita but a disappointing last in the Louisiana Derby after a bad break.

Trainer-owner-breeder Harold J. Rose’s Hal’s Hope became the first colt to win a key Kentucky Derby prep, when he captured the Florida Derby after a long stretch duel with High Yield on March 11 at Gulfstream.

Frank Brothers also served notice that his Mighty, who closed at 23-1 in the Kentucky Derby Future Wager Pool Two, needs to be taken more seriously after a dynamic stretch run that captured the $750,000 Louisiana Derby by two lengths on March 12.

Meanwhile, Todd Pletcher was squaring off with a double-barreled shot at the Derby with his More Than Ready, who ran a strong second in the Louisiana Derby after leading, and the undefeated Trippi, winner of the Swale Stakes on the Florida Derby undercard.

Neil Drysdale, whose A.P. Indy probably would have won the 1992 Derby had he not come up with an injury and been scratched, has a promising trio of prospects for this year’s Run for the Roses. Both his War Chant, the impeccably bred colt who won Santa Anita’s Grade II San Rafael Stakes, and Fusaichi Pegasus, the $4-million colt who beat an excellent field in the San Felipe, are major players, while his Toqueville, a French Deputy colt, is lightly raced but well regarded.

Other leading trainers with serious Derby contenders at ATM press time included Alex Hassinger, whose BC Juvenile winner Anees, second choice in Kentucky Derby Future Wager Pool Two at 10-1, ran third in the San Felipe in preparation for the Santa Anita Derby; Robert Frankel with the duo of Cocky, a close third in the San Rafael Stakes, and Aptitude, second in the Grade III Gotham; Jenine Sahadi, whose The Deputy whipped 1-2 favorite Captain Steve in the Grade II Santa Catalina and ran second in the San Felipe; Joe Orseno, whose undefeated Red Bullet, winner of the Gotham, has a powerful late punch tailored to the Derby; and two-time Derby winner Nick Zito, whose Rollin With Nolan, a Gulfstream allowance winner, has to pinch-hit for Greenwood Lake, who was removed from Derby contention after an injury.

• Be certain your top selection can go the classic 1?-mile Derby distance. Although somewhat discredited in recent years, the Dosage-Index factor served as a reliable guide for many years in selecting a horse that could compete effectively at the Derby distance. Be wary of any entrant with a dosage index over 4.0. If a major Derby-prep winner has a dosage index over 4.0, look closely at his pedigree. If he doesn’t have an outstanding sire, who could win at classic distances, then you may want to eliminate him from consideration.

Dual qualifiers — horses with a dosage index of 4.0 or less and which are rated within 10 pounds of the top-weighted male in The Jockey Club’s Experimental Free Handicap — have done well in the Derby. Dual qualifiers won five Derbys in the ’90s while accounting for only 23% of the starters.

This year, nine colts and three fillies are dual qualifiers. The colts are Anees, Captain Steve, Dixie Union, More Than Ready, Chief Seattle, High Yield, Exchange Rate, Mull of Kintyre and Scottish Halo. The fillies are Cash Run, Surfside and Circle of Life.

• Eliminate any horse that has run poorly at Churchill Downs, but move up on your list any horse that has won or raced extremely well at Churchill. This significant horse-for-course factor is sometimes overlooked.

Churchill horses-for-course which are slated to run in this year’s Derby include Captain Steve, who won the Kentucky Jockey Club last year; More Than Ready, winner of the $120,000 WHAS Stakes; and Mighty from the hot barn of trainer Frank Brothers, who won Churchill’s Iroquois and was second to Captain Steve in the Kentucky Jockey Club.

• Study the betting action in the three Kentucky Derby Future Wager pools, particularly the final one, April 13-16, a period that covers the Blue Grass Stakes, the Wood Memorial and the Arkansas Derby. Today’s bettors, probably more sophisticated than those of past years, have a way of targeting likely contenders.

• Compare Derby entrants’ Churchill workouts, paying close attention to those at five furlongs or longer. Pay particular attention to horses who’ve earned bullets, the fastest drills of the day. Silver Charm fired three straight Churchill bullets before winning the 1997 Derby.

Once you’ve narrowed your Derby list to three, four or maybe five horses, consider betting strategies.

It might be profitable to use all of your Derby selections in a Pick Three. (This year there will be three Pick Threes that include the Derby.) Look at the races on either side of the Derby, and try to limit selections to two or three in each of the non-Derby legs of your Pick Three.

For example, if you bet races six, seven and eight (the Derby), and you use two horses in the sixth, three in the seventh and five in the Derby — excellent coverage — the total cost is only $30 for a $1 ticket. If one of the non-Derby legs includes a fat overlay, this Pick Three can produce a whopping payoff.

Last year, when there were only two Pick Threes that included the Derby, the payoffs were fantastic. The Pick Three payoff starting with race six paid $2,995.00 (a $1 ticket paid half that amount), and the Pick Three starting with race seven paid $816.40 (half of that on a $1 ticket). In the sixth race, the winner, Zuppardo Ardo, paid $10.60; in the seventh, the winner, Wild Event, paid $13.20; and Derby winner Charismatic paid $64.60. Even with 3-5 favorite Golden Temper (an obvious ace) winning the ninth, the Pick Three on races seven, eight and nine was still a tremendous overlay.

Nearly every year, the exacta and trifecta payoffs in the Derby also are whoppers. For example, the two logical choices in the 1998 Derby — Captain Bodgit (the favorite) and Silver Charm (the second choice) — used in a $2 exacta box at a cost of $4, paid $31.00, a very nice return. Florida Derby winner Thunder Gulch, played on top in a trifecta with 8-1 Tejano Run second and favorite Timber Country (coupled with Serena’s Song) third, produced a monster $2,099.20 for just $2 in the 1995 Derby.

Derby Day is nearly always Payday for the sharp and daring handicapper. 

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