Betting the Kentucky Derby: How to Wager and Win on America's Biggest Horse Race
Big-Race Days The Good Ol' Days When I was 11 or 12 years old I used to enthusiastically walk a mile or so from my parents' rental up Central Avenue to Yonkers Raceway, now known as the illustrious Empire City Racino. Back in those days I was financially loaded for bear. My bankroll consisted of $5, and I would like to say I earned it by mowing the neighbor's lawn or taking out the trash. The truth is, my father gave me the $5 starting bankroll. Now that I look back many years later, it probably was some type of small-time bribe for all the afternoons we snuck to the track when my mother thought we were at the beach, zoo, amusement park, shopping for groceries, or at a Yankees game. I believe the correct term for my old man was "juvenile enabler." My father was even kind enough to throw in an advance program, which he picked up at Dan's Tobacco & Candy store after working the 12:00 to 8:00 shift. In those days, $5 was all a responsible and patient harness handicapper needed to succeed. If you could expertly and confidently collect 9 or 10 show bets on drivers Carmine Abbatiello and Rejean Daigneault at $2.60 or $2.80 a pop, you were well on your way to a successful career. On the good nights when Carmine or Rejean didn't make an unexpected stretch break at 3-5, I'd leave the track with a $12 or $15 profit. All was well in the world of high-stakes harness-racing betting. Unfortunately, a lot has changed since the days of my harness-racing show parlays. The game has gotten considerably tougher to beat with a traditional "grind-along" style of play while attempting to compete with shrewder players and unimaginable advancements in technology. For starters, the parimutuel competition is much more prepared today than it was 15 or 20 years ago. Intricate computer programs that can track live odds and weaknesses in the betting pools, advanced trainer and pedigree information, superior speed and pace figures, and sophisticated betting syndicates (which are heavily bankrolled and professionally managed) in the United States and overseas make it much more difficult for the average player to find any value.  Today, there are only a handful of bettors that consistently wager on the traditional win, place, and show format with any degree of success. There are just too many obstacles for this type of player to succeed in today's game. But do not despair! Today's horseplayer has a tremendous opportunity that was not available to his counterpart of several decades ago--a vast array of betting options beyond win, place, and show.  That's a strong advantage in day-to-day play, but even more so on racing's biggest days--and  there is no bigger day or bigger opportunity than America's most famous horse race, the Kentucky Derby at Churchill Downs on the first Saturday in May.     Big-Race-Day Guaranteed Multi-Race Pools Today, the most successful players are those that consistently adjust to the changing times and have learned to save their bankrolls for the bettor-friendly, multirace bets, many of which have guaranteed pools.  In these types of pools we're essentially looking for a collection of bettors that consist of the fewest tiger sharks and are instead bloated with schools of lazy winter flounder. Where do we find these uninformed, lethargic bettors? Fortunately, they exist almost every weekend of the year at racetracks across the country. The following monthly schedule of racetracks and big-race days offers the savvy handicapper the opportunity to play into portly pools where there are guaranteed to be uninformed bettors coughing up uninformed dollars.  These types of days are what I like to call the New Year's Eve of racing days. You have your amateur sloppy drinkers on New Year's Eve, and you have your legion of recreational bettors on big-race days. There's nothing more appealing to the seasoned pro than watching the "Uncle Leos" and "Cousin Gracies" of the world betting on birthdays, anniversaries, favorite colors, and names of horses and jockeys. These big-race days are usually heavily advertised in the local media and consistently bring out novice fans and fledgling bettors. Mark your calendars and clear out the bank account. Month Racetrack Big-Race Days January Gulfstream/Santa Anita Sunshine Millions February Gulfstream Park Swale, Holy Bull Stakes, Donn Handicap February Fair Grounds Mineshaft H., Fair Grounds Handicap,               Silverbulletday Stakes, Risen Star Stakes March Gulfstream Park Gulfstream Park Handicap, HutchesonStakes, Richter Scale Handicap,  Fountain of YouthMarch Santa Anita Frank E. Kilroe Mile Handicap, Robert B.Lewis Stakes, Santa Anita Handicap March Aqueduct Gotham Stakes March Fair Grounds Fair Grounds Oaks, Louisiana Derby March Bay Meadows El Camino Real Derby March Santa Anita Santa Anita Oaks March Tampa Bay Downs Hillsborough Stakes, Tampa Bay Derby March Sunland Park WinStar Oaks, WinStar Derby March Turfway Park Lane's End Stakes March Nad Al Sheba (Dubai) Dubai World Cup, UAE Derby March Gulfstream Park Florida Derby April Aqueduct Bay Shore Stakes, Wood Memorial April Santa Anita Santa Anita Derby, Potrero GrandeHandicap April Hawthorne Illinois Derby April Aqueduct Carter Handicap, Withers Stakes April Keeneland Vinery Madison Stakes, StonersideBeaumont Stakes, Maker's Mark Mile,Toyota Blue Grass Stakes, CommonwealthStakes, Coolmore Lexington Stakes April Oaklawn Park Arkansas Derby May Churchill Downs Kentucky Oaks, Kentucky Derby May Lone Star Park Lone Star Derby May Pimlico Black-Eyed Susan, Preakness May Belmont Park Peter Pan, Metropolitan Handicap May Hollywood Park Shoemaker Mile Stakes, Gamely Stakes June Thistledown Ohio Derby June Belmont Park Belmont Stakes, Mother Goose Stakes,Suburban Handicap June Colonial Downs All Along Stakes, Colonial Turf Cup June Churchill Downs Stephen Foster Handicap June Prairie Meadows Iowa Oaks June Hollywood Park Hollywood Gold Cup July Hastings Lt. Governor's Handicap July Woodbine King Edward July  Belmont Park Dwyer Stakes July Calder Princess Rooney Handicap, Smile Sprint Handicap, Carry Back Stakes July Monmouth Park United Nations July Hollywood Park American Oaks, Triple Bend Handicap,CashCall Mile, Swaps Stakes July Delaware Park Delaware Oaks July Colonial Downs Virginia Derby July Del Mar Eddie Read Handicap, BingCrosby Handicap July Saratoga Whitney Handicap, Go For Wand,Alfred G. Vanderbilt Handicap, DianaHandicap, Jim Dandy August Saratoga Alabama, King's Bishop,  Travers, Sword Dancer Invitational August Del Mar Del Mar Handicap, PacificClassic August Mountaineer Park West Virginia Derby August  Monmouth Park Oceanport Stakes, Matchmaker   Stakes, Haskell Invitational August Arlington Park Secretariat Stakes, Arlington Million,Beverly D. Stakes September Saratoga Woodward, Forego Handicap,Spinaway Stakes, Hopeful Stakes September Philadelphia Park Pennsylvania Derby September Del Mar Del Mar Futurity, Del Mar DebutanteStakes September Belmont Park Man o' War, Ruffian Handicap, Futurity Stakes, Gazelle Stakes, Brooklyn Handicap,Jockey Club Gold Cup, Beldame Stakes,  Joe Hirsch Turf Classic, Vosburgh Stakes,Flower Bowl Invitational, Kelso Handicap September Santa Anita Yellow Ribbon Stakes, Oak Leaf Stakes,Goodwood Handicap, Norfolk Stakes September Woodbine  Woodbine Mile, Canadian Stakes, SummerStakes September Louisiana Downs Super Derby September Turfway Park Kentucky Cup Classic, Kentucky CupJuvenile Stakes, Kentucky Cup Sprint,Turfway Stakes September Hawthorne Hawthorne Gold Cup October Breeders' Cup October Keeneland Darley Alcibiades Stakes, SycamoreStakes, Shadwell Turf Mile, Lane'sEnd Breeders' Futurity, JuddmonteSpinster Stakes, Queen Elizabeth IIChallenge Cup October Belmont Park Frizette Stakes, Jamaica Handicap,Champagne Stakes, Jerome Handicap October Santa Anita Clement L. Hirsch Turf, AncientTitle Handicap, Lady's Secret Handicap,Oak Tree Mile  October Woodbine Canadian International, E.P. Taylor Stakes November Aqueduct Cigar Mile, Remsen Stakes, DiscoveryHandicap December Calder My Charmer Handicap, Tropical TurfHandicap December Hollywood Park Hollywood Starlet, CashCall Futurity Every year, around the start of the Triple Crown season and before the Breeders' Cup, acclaimed author and handicapper James Quinn writes an article about the necessity of having a fat wallet in preparation for a realistic assault on these upcoming big-race days. After all, these are the days when potential boxcar exotic scores exist and there are plenty of ripe apples in the betting basket. This sound money-management advice is one that the average handicapper and player should adhere to. In fact, I'd even go so far as to recommend that you cut out Quinn's annual betting-advice column and give it a permanent space on the refrigerator next to the household-chore wish list that's collecting dust. Although each handicapper's betting platform and financial comfort zone differs, do what you can to fatten your bankroll for these types of big-race days - even if it means sitting on the betting sidelines for several weeks.  Remember: It only takes a few races and one special afternoon to make up for months of missed photos and tough beats.