I had to consult his PPs...

You have the right race, the right odds and the first time blinkers.. but... it wasnt Montreal Red, it was Wild Escapade. Montreal Red was about 3-5 in the Hopeful that year and finished second...

I know this is dating me,but I'm surprised no one has mentioned Hoist The Flag.

Graustark in the 60's.

Sir Gaylord, injured before the 1962 Derby. I don't thing Buckpasser or Dr.Fager ran in their derbies either.

Not necessarily horses that would have won, but some who would have had a fighting chance:

'88- Cherokee Colony
'89- Prized
'90- Roanoke
'91- Olympio, Compelling Sound, Scan
'92- A.P. Indy, Bertrando
'93- Peteski, Miner's Mark, Colonial Affair, Strolling Along

Dixie would not be very happy if he read this....as we all know, the best that Calumet ever had (and that Dixie galloped and trained personally) was Coaltown.

I think Man O' War would have had a decent shot in the 1920 Derby.

AP Indy is the one that seems obvious from the last 20 years or so.

How about Silverbulletday? I think she was faster than that crop of colts in the spring of 1999, and she dominated the Oaks in a faster 9f than the boys ran the next day.

She didn't seem faster in the Belmont.

Hoist the Flag, of course - beat the same horses who were winning other preps, by daylight and with glee. And with him out, Good Behaving, who beat the same horses in the Wood and Gotham. But Good Behaving wasn't Derby nominated and no supplements in those days.

Buckpasser out with quarter cracks; Derby went to Kauai King??? who couldn't finish in the same furlong with the champion.

The Derby scenario would have been hard on Dr. Fager, like the famous Woodward where he was run into the ground by a rabbit. The Good Doctor wasn't a natural 10f horse; he won at the distance on his class.

One who ran in the Derby and should have won was Blue Larkspur. The track came up muddy but BL's trainer had gone to the hospital with appendicitis and nobody in the stable felt they had the authority to get him shod with mudcaulks. Slipped and slided to fourth.

this is the horse i was trying to think of. definitely a sad story, a star crossed talented horse for sure.