The 3 Greatest Kentucky Derby Champions of All Time

One of my favorite things about sports is something that doesn’t take place at the competition venue. Sure, those who were in the stands when Babe Ruth allegedly “called his shot” witnessed a historic moment. The lucky fans who watched Wilt Chamberlain pour in 100 points in an NBA game against the New York Knicks on March 2, 1962, saw a basketball legend at his very best.

But the most entertaining part of sports — at least to me — is not watching a Hall-of-Famer go off on a guy with a career scoring average of 7.2 points per game (PPG), like Darrall Imhoff, who started at center for the Knicks that historic night. To me, the most entertaining part of sports is debating the answer to a simple question:  What if?

What if Chamberlain played a one-on-one game of hoops with Michael Jordan? What if Ruth was stared down by Corey Kluber with the bases loaded and two outs in the bottom of the ninth inning? What if Sid Luckman, the man who pioneered the position of quarterback, faced off with Tom Brady, the man who has defined it for the past century (or so it seems). A Brady-Luckman showdown would have particular appeal to me because Luckman also played defensive back.

My point here is that the history of sports is what makes them so compelling. After all, without the context that history provides, there can be no greatness. Scoring 100 points in an NBA game is only noteworthy because no one — except Chamberlain — has ever done it.

It was with this in mind that I decided to peruse my database of Kentucky Derby results and present what I believe are the top three greatest performances in Derby history.

Now, anybody who has delved into the history of sports knows that it is not easy to determine greatness by statistics alone.

Things change.

For example, during the 1961-62 season, in which Chamberlain averaged 50.4 PPG, the typical NBA team took 107.7 shots per contest. By the time Jordan was leading the Chicago Bulls to their last title in 1998, teams were attempting just 79.7 shots per game.

Likewise, the racing strip at Churchill Downs, the site of the Kentucky Derby, has changed over the years — making straight time comparisons fruitless. However, as many regular readers know, I have developed my own pace figures, which measure relative speed, so I will be relying heavily on them to make my assessments.

Hence, a quick tutorial is in order:

Early Speed Ration (ESR)

A measurement of a horse’s early energy expenditure in relation to the total race requirements. The lower the figure, the greater the horse’s early exertion in that event.

-15= Demanding.
-10= Brisk.
  -5= Moderate.
   0= Soft.

Late Speed Ration (LSR)

A measurement of a horse’s late energy expenditure in relation to the total race requirements. The higher the figure, the greater the horse’s late exertion in that event. Because late speed is calculated at a time when a horse is being asked for his/her maximum effort, LSRs can be a great indication of form as well.

   0= Excellent.
  -5= Good.
-10= Fair
-15= Poor.

Pace Profile

A simple comparison between a horse’s LSR and the ESR of the race in which it was earned. Positive profiles are greatly desired.

#3 OLD ROSEBUD (1914)

Old Rosebud’s zero LSR ranks as the fifth-highest in Kentucky Derby history and the best ever for a wire-to-wire winner of America’s most prestigious horse race. What’s more his final time of 2:03 2/5 set a Derby record that would stand for 16 years.


Old Rosebud (photo via

#2 WHIRLAWAY (1941)

Whirlaway had great timing. Not only did he possess a potent late kick, but he knew when to raise his game — which he did on the first Saturday in May of 1941. Not only did Whirlaway win the Derby by eight lengths that day, he also recorded a +1 LSR and set a new track record (2:01-2/5) that wasn’t broken until 1957.


No horse — past, present and probably future — ever had the kind of spring that Secretariat had in 1973. After getting upset by stablemate Angle Light in the Wood Memorial, “Big Red” produced a series of efforts that culminated with a Triple Crown, an Eclipse award for Horse of the Year and a new name: legend.

Secretariat’s 1:59-2/5 clocking remains a Kentucky Derby record and his +3 LSR is tied with His Eminence for the best ever.

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