Whirlaway was widely known as "Mr. Longtail" because his tail was especially long and thick and it would blow far out behind him during races, flowing dramatically in the wind.

[2] The champion colt had a habit of "bearing out," drifting toward the middle of the racetrack, during the latter part of his races and losing as a result.

In preparations for the Kentucky Derby, this had been such a problem that trainer Ben A. Jones fitted the colt with a full-cup blinker over his right eye.

In Whirlaway's final workout before the Derby, Jones cut a small hole in the blinker so that the horse had a tiny field of vision.

Jones positioned himself ten feet off the inner rail and told jockey Eddie Arcaro to ride the horse through that space.

[6] Arcaro was the sole rider for Whirlaway in all of his 3-year-old victories, but dismounted for most of the 1942 season, when he served a long suspension for racing infractions.

[7] On July 15, Whirlaway broke the Suffolk Downs track record for a mile and one-eighth with a time of 1:48 1/5 in winning the Massachusetts Handicap.

On September 19, 1942, Alsab defeated the Triple Crown champion in a match race at Narragansett Park in Pawtucket, Rhode Island.

On December 12, more than twenty thousand people turned out to watch Whirlaway win the inaugural Louisiana Handicap at the Fair Grounds Race Course.