Classic Empire was retired due to multiple setbacks from an abscess on his right front hoof, as well as slight back problems which plagued him throughout his career.

[3] As a yearling being prepared for sale, Classic Empire was described by his handlers as a "very well-bodied, medium-sized horse, he kind of stood out for folks."

"[3][1] Classic Empire gained a reputation as being a bit of a "bad-boy" in his racing career, after unseating his rider in the Hopeful Stakes and refusing to breeze on several occasions.

He doesn't have a mean bone in his body...."[6] Jockey Florent Geroux, who had fallen off the horse during a workout early on in his two-year-old year, commented, "it's not like he wants to hurt you or anything.

Sent off as the 1-2 favorite and ridden by jockey Julien Leparoux, he broke slowly and rallied from the back of the field to win by 1 1/2 lengths under a hand ride on a track rated as sloppy.

[13] His connections then announced that he would start in the Breeders' Futurity Stakes at Keeneland on October 10, where he would wear blinkers for the first time.

Classic Empire broke quickly and stalked the early front runners before making a strong move around the turn, pulling away to win by three lengths.

[16] Classic Empire was then entered in the Breeders' Cup Juvenile on November 5, which was run at Santa Anita Park, in a race that was considered wide open.

"[17][16] The close finish made Classic Empire and Not This Time the early co-favorites in the Kentucky Derby future wagering.

[18] Two weeks after the Breeders' Cup, it was announced that Not This Time would be retired due to an injury,[19] which made Classic Empire the sole early Kentucky Derby favorite.

[20] On January 21, 2017, Classic Empire was named the American Champion Two-Year-Old Male Horse of 2016, receiving all of the 248 votes.

[22] Classic Empire entered the race with a relatively short work tab, with only four workouts in a span of twenty days.

"[26] Although Classic Empire seemed to come out of the race in good order, Casse subsequently discovered an abscess on the right front hoof.

"[30] Classic Empire's next goal was supposed to have been the Blue Grass Stakes on April 8, but on March 19 at Palm Meadows Training Center, he refused to break off and breeze, for no apparent reason.

[35] Classic Empire stayed calm and relaxed throughout the post-parade, unlike before the Holy Bull, and loaded into the starting gate quietly.

He then unleashed a sustained rally, and, despite switching to the wrong lead near the wire, got up to beat Conquest Mo Money by half a length, with a time of 1:48.93.

"[37][38] The day after the race, Classic Empire appeared to be in great shape, with Casse saying: "I know what happened at Gulfstream was because of his foot abscess because he was an entirely different horse yesterday.

The track was labelled as "Wet Fast (sealed)",[40] with some standing water due to persistent rain over the course of several days.

More than a dozen lengths behind in 13th in the early part of the race, Classic Empire started closing ground around the far turn and into the stretch, only to be bumped again by McCraken.

"[41] Classic Empire came out of the race with some superficial cuts and a swollen right eye; The day after the Derby, he was barely able to open it due to swelling.

[44] At the start, he bobbled slightly but went out to the lead, pressured the favorite, Always Dreaming, as they went through a moderately fast half mile of 46.81 seconds.

Chad Brown, the trainer of Cloud Computing, praised Classic Empire after the race, stating: "I'm not going to dispute the fact that I brought in a fresh horse as part of our strategy.

[52] At Saratoga, Classic Empire was fine physically, but he was not enthusiastic about training, which Mark Casse attributed to the humidity.|[53] His connections decided to skip the Travers and wait for the Pennsylvania Derby, where he would have more time to prepare and the weather would be cooler.

[55] Mark Casse then announced that Classic Empire would also skip the Pennsylvania Derby but stay in training with no particular race being targeted.

His foot abscess took longer to heal than initially expected, and the colt ran out of time to return to form for his intended year-end start, the Breeders' Cup Classic.