On this date in 1990, boxer James “Buster” Douglas did the unthinkable when he decked heavyweight champion and phenom Mike Tyson as a 41-1 underdog. It was a glorious kickoff to sports in the decade of the 1990s. A few months later, we’d witness Mrs. Genter get the hugs of Carl Nafzger and the tears of America as Unbridled wore the roses. Little did we know then that the entire decade of the 1990s, just as the 1980s, would see favorites get blanked in the Kentucky Derby. 

We love a great upset in horse racing, but the Derby has been absent of them for the past six years. Consecutive favorites Orb, California Chrome, American Pharoah, Nyquist, Always Dreaming and Justify have numbed us to the potential for chaos. We haven’t seen anything like this parade of chalk in our lifetimes; six in a row haven’t won since the late 1800s, after all. 

It’s hard to believe that in 2015, I was already itching for a Derby upset. As part of the NBC Sports research team, I was then pitching a story about what we had already started to miss with the formful results. The producers nixed the idea; it never made the air. But reading today of the Douglas-Tyson anniversary got me thinking again, just what it might take to see another puzzler on the first Saturday in May. 

Pardon the all caps (that’s TV script style), but here’s the 2015 NBC piece I pitched as we think about historic upsets on a historic anniversary: 

ANATOMY OF A DERBY UPSET 

BACK-TO-BACK KENTUCKY DERBY FAVORITES HAVE BASKED IN THE ROSES, ORB AND CALIFORNIA CHROME, LENDING CALM TO AMERICA’S MOST CHAOTIC HORSE RACE. BUT FOR THOSE OF YOU WHO BELIEVE IN MIRACLES ON ICE, AND THE UPPER CUT OF JAMES ‘BUSTER’ DOUGLAS, THE NEXT UPSET MAY ONLY BE A MILE AND ONE-QUARTER AWAY. 

THIS DERBY MARKS THE 10TH ANNIVERSARY OF ONE OF ITS MOST UNLIKLIEST OF WINNERS, A 50-TO-1 OUTSIDER NAMED GIACOMO. THE UNHERALDED GREY, IRONICALLY OWNED BY A&M RECORDS CO-FOUNDER JERRY MOSS…AND NAMED FOR THE SON OF MUSICAL GREAT ‘STING’…PROVED TO BE ONE OF THE BIGGEST ONE-HIT WONDERS IN THE RACE’S HISTORY. A $1 WINNING TICKET ON THE TOP 4 FINISHERS IN DERBY NUMBER 131 WAS WORTH MORE THAN $860,000. 

A 50-TO-1 KENTUCKY DERBY WINNER HAD NOT BEEN SEEN IN 92 YEARS BEFORE GIACOMO LIT UP THE CHURCHILL DOWNS TOTEBOARD. BUT YOU DIDN’T HAVE TO WAIT LONG FOR LIGHTNING TO STRIKE AGAIN. JUST FOUR YEARS LATER, ANOTHER 50-1 SHOT … MINE THAT BIRD … SPLASHED UP THE RAIL TO BAFFLE THE EXPERTS AND SET THE DERBY AXIS ON TILT. 

WERE HORSES LIKE GIACOMO AND MINE THAT BIRD RANDOM POSSIBILITIES, OR MIGHT THERE BE AN ANATOMY OF THE UPSET IN THE KENTUCKY DERBY? 

EACH OF THE FOUR LARGEST UPSETS IN KENTUCKY DERBY HISTORY OCCURRED IN YEARS AFTER A FAVORITE HAD SCORED. GIACOMO FOLLOWED SMARTY JONES, MINE THAT BIRD FOLLOWED BIG BROWN....EVEN 91-1 DONERAIL BOASTED HIS RECORD RETURN THE YEAR AFTER AN ODDS-ON FAVORITE TALLIED THE 1912 DERBY. JUST WHEN THE PUBLIC THINKS IT HAS THE DERBY DIALED IN, THE ORDER CAN BE SHAKEN IN HISTORIC WAVES. OVER-CONFIDENCE HAS NO KENTUCKY HOME ON THE FIRST SATURDAY IN MAY. 

ANOTHER FACTOR SHARED BY THE DERBY’S BIGGEST UPSETTERS IS A LATE-RUNNING STYLE. AMERICAN HORSEPLAYERS ARE DRAWN TO SPEED LIKE A MAGNET, AND THOSE WHO RALLY FROM FAR BACK OFTEN ARE CONSIDERED TOO SLOW FOR PRIME TIME. OF THE TOP 5 UPSETTERS IN KENTUCKY DERBY HISTORY, THEIR AVERAGE POSITION IN A 20-HORSE RACE COLLECTIVELY WOULD HAVE BEEN 15TH IN THE EARLY RUNNING. MINE THAT BIRD EMERGED FROM 19TH, GIACOMO FROM 18TH, IN MOST RECENT EXAMPLES. 

AND FINALLY, A DERBY BOMB DOESN’T GET DROPPED WITHOUT A SKILLED PILOT. OF THE FIVE LARGEST KENTUCKY DERBY UPSETS OF THE LAST HALF-CENTURY, ALL FIVE WERE RIDDEN BY JOCKEYS WHO WOULD GO ON TO BE ENSHIRED IN THE HALL OF FAME. CURRENT NAMES LIKE CALVIN BOREL, MIKE SMITH AND GARY STEVENS, ALONG WITH PAST LEGENDS LIKE BOBBY USSERY AND CHRIS ANTLEY. IT TAKES ALL THE STARS TO ALIGN IN THE LOUISVILLE SKYLINE. 

I hope you enjoyed this look back, and perhaps look ahead to bigger prices on the horizon. Who knows, after six years of over-flowing chalk, over-confidence on this coming first Saturday in May might be at an all-time high? If so, put up your dukes, Buster.