1920: Three-year-old season
In 1920, Johnny Loftus was denied a renewal of his jockey's license by The Jockey Club, a development that was rumored to be related to Man o' War's defeat in the Sanford. He was replaced as the colt's rider by Clarence Kummer. Over the winter, Man o' War had grown to 16.2 hands (66 inches, 168 cm) high and filled out to about 1,150 pounds (520 kg) with a 72 inches (180 cm) girth.
Riddle decided early on to restrict Man o' War to races within his own age division, in large part because the most valuable races in the country were restricted to three-year-olds. He decided not to enter him in the Kentucky Derby because it was run only a few days before his preferred target, the Preakness Stakes, which was held close to the Riddle farm where Man o' War had spent the winter. Riddle also did not like racing in Kentucky and believed it was too early in the year for a young horse to go a mile and a quarter. Thus, Man o' War did not have a chance to complete what later became known as the U.S. Triple Crown of Thoroughbred Racing, consisting of the Kentucky Derby, Preakness Stakes, and Belmont Stakes. The previous year, Sir Barton had won the three races, which gained in prestige and importance 10 years later when Gallant Fox accomplished the same feat under a great deal of media attention.
Instead, Man o' War made his three-year-old debut on May 18 in the Preakness Stakes, then run at a distance of 1+1⁄8 miles. Despite the long layoff and never having raced beyond six furlongs (1,200 m), he went off as the 4-5 favorite in a field of nine horses that included his old rival Upset, who had finished second in the Derby. Man o' War broke alertly and took the lead within the first 10 yards, then established a two-length lead down the backstretch while under restraint. As they rounded the final turn, Upset started to close ground so Kummer loosened his grip. Man o' War responded by again pulling away, completing the opening mile in what would have been a new Pimlico track record of 1:383⁄5. Eased in the final furlong, he won by 1+1⁄2 lengths over Upset in a final time of 1:513⁄5.
The horse was then returned to his home base at Belmont Park, where a crowd of 25,000 turned out to watch him in the Withers Stakes on May 29. He was sent off at "generous" odds of 1–7 against two rivals: Wildair, winner of the Metropolitan Handicap who was at odds of 6–1, and the overmatched David Harum at 30–1. Man o' War again seized the early lead, completing the first quarter-mile in :23+3⁄5 while tugging at the bit. When Wildair tried to close ground around the turn, Kummer briefly released his hold and Man o' War opened up his lead again. Eased in the final sixteenth of a mile, he won by two lengths while setting an American race record of 1:354⁄5 for the mile.
Man o' War's next start was on June 12 in the Belmont Stakes, then run at a distance of 1+3⁄8 miles. The race establish him as one of the all-time greats with an "almost unbelievably brilliant performance" before a crowd of 25,000. At odds of 1-20, he faced one rival, the well-regarded colt Donnaconna. Man o' War led from the start, and Kummer let him run freely at the top of the stretch, allowing Man o' War to draw away by 20 lengths. Although eased in the final furlong, he set a world record of 2:141⁄5, beating the previous standard set in England by over two seconds and beating Sir Barton's American record by over three seconds. This time stood as the American record for the distance until 1961, when Wise Ship ran 1+3⁄8 miles in 2:14 flat on a turf course. It stood as the American dirt record until 1991.
Ten days later, Man o' War returned in the Stuyvesant Handicap, which he won against one rival. His odds of 1 to 100 were believed to be the lowest ever offered in an American horse race.
His next start in the Dwyer Stakes on July 10 proved far more demanding. The colt John P. Grier, who had challenged Man o' War in the Belmont Futurity at age two, had matured into the second-best three-year-old in the country. Under the conditions of the Dwyer, Man o' War was assigned 126 pounds while John P. Grier carried only 108. The two colts scared away all rivals, turning the Dwyer into a match race. They raced side by side down the backstretch, with Man o' War on the rail blocking John P. Grier from the view of the spectators. The horses ran the race as a sprint, completing the first three-quarters of a mile in 1:09 2/5 – an American record. As they entered the turn, Man o' War started to open up an advantage but John P. Grier rallied and got back on even terms. They completed the mile together in a time of 1:35 3/5, breaking Man o' War's American record set in the Withers. John P. Grier made another surge, and for a moment the spectators believed that he would win the race. Kummer then hit Man o' War with the whip, and he made a final surge, opening up a lead of two lengths in the final fifty yards. The final time was 1:49 1/5, a world record for 1+1⁄8 miles.
Man o' War was then shipped to Saratoga and was entered in the Miller Stakes on August 7. There was a then-record crowd of 35,000, many of whom gathered in the saddling area where Man o' War was surrounded by twelve Pinkerton guards. His jockey for the race was Earl Sande, replacing an injured Kummer. As expected, Man o' War took the early lead and was unchallenged in a six-length victory. He had been tightly restrained, but even so, his time of 1:56 3/5 for the distance of 1+3⁄16 miles was just 3⁄5 seconds off the track record. "I never felt anything like that horse in my life," said Sande after the race. "He strides farther than anything I ever rode and does it so handily that you would not think he was running at all."
His connections had a brief scare when Man o' War exhibited signs of lameness after a workout on August 17, but he quickly recovered. On August 21, he entered the Travers Stakes where he faced his two strongest rivals: Upset for the fifth and last time, and John P. Grier for the third time. A record crowd overflowed the grandstand and stretched down the rail and track apron. As a result, Saratoga management opened the infield, and 5,000 people moved across the track to line the inner rail.
Man o' War's jockey for the race was Andy Schuttinger as Kummer was still recovering from injury and Sande was not available. After the start, John P. Grier tried to match strides with Man o' War but could not keep up. After establishing a clear lead by the first turn, Schuttinger took hold of Man o' War for the rest of the race. Upset made a late run to move into second, but Man o' War won by three lengths. Despite not being extended, he completed the distance of 1+1⁄4 miles in 2:01 4/5, equaling the track record set earlier in the year by Sir Barton. This record stood until 1941. It is possible the time was also a world record, as the existing record time of 2:00 flat credited to Whisk Broom II in 1913 was disputed.
Riddle contemplated entering Man o' War against older horses for the first time in the $5,000 Saratoga Gold Cup but ultimately chose to enter the $15,000 Lawrence Realization Stakes against three-year-olds instead. When his only rival scratched from the race, it nearly became a walkover until Mrs. Riddle's niece, Sarah Jeffords, entered Hoodwink. To compensate for the lack of competition, Riddle announced that Man o' War would be allowed to show his speed. He was reunited with regular jockey Kummer, after being ridden by Sande and Schuttinger while Kummer recovered from an injury. Kummer neither restrained the horse nor urged him at any point in the race. Running as he pleased, Man o' War won by slightly more than a quarter-mile – the official margin was 100 lengths – while setting a world record of 2:40 4/5 for a mile and five-eighths. This broke the world record set in England by 1+3⁄5 seconds and lowered the American record by over four seconds. This world record stood until 1956, when it was broken by Man o' War's great-grandson Swaps.
The performance drew superlatives from the racing community. Turf writer B.K. Beckwith later called it "the most astounding display of arrogant annihilation", adding, "[Man o' War] was like a big red sheet of flame running before a prairie wind". The New York Times commented, "at Belmont Park yesterday [Man o' War] gave what was undoubtedly the greatest exhibition of speed over a considerable distance of ground ever witnessed anywhere."
Man o' War's next start was the Jockey Club Gold Cup on September 12, the first time he entered a race open to older horses. The race organizers tried to lure Sir Barton into entering by promising to increase the purse from $15,000 to $25,000 if he did so, but Sir Barton needed more time to recover from his last race. It was also speculated that Sir Barton's owner was holding out for an even higher purse for a match race with Man o' War. The connections of Exterminator, another future Hall of Famer, were also considering the race but bypassed it because, under the weight-for-age conditions of the Gold Cup, he would have had to concede Man o' War five pounds. As it was, Man o' War faced only one competitor and won under tight restraint by fifteen lengths. Although it was declared a hollow victory by The New York Times, Man o' War still set an American record for 1+1⁄2 miles of 2:28 4/5, breaking the existing mark by 4/5 seconds.
Man o' War next entered the Potomac Handicap at Havre de Grace Racetrack in Maryland on September 18. He was assigned 138 pounds, conceding from 24 to 34 pounds to his rivals, which included Kentucky Derby winner Paul Jones. Man o' War faced an early challenge from Blazes, then turned back a late run by Wildair to win by 1+1⁄2 lengths while breaking the track record by 1⁄5 seconds. Although Man o' War was not seriously challenged, the high weight and a poorly maintained racing surface took a toll: He came out of the race with a swollen tendon on his right foreleg.
The final start of Man o' War's career came in Windsor, Ontario, Canada, in the Kenilworth Park Gold Cup on October 12. The event was so highly anticipated that it became the first horse race to be filmed in its entirety, with the resulting footage later shown in movie theaters across the country. The race was originally intended to be a face-off between the three great horses of the time: Man o' War, Sir Barton, and Exterminator. However, the owners of Sir Barton and Man o' War agreed to a distance of 1+1⁄4 miles, which was too short for Exterminator to run his best, and they agreed to a weight-for-age format, under which the older Exterminator would concede weight to Man o' War. Therefore, Exterminator was not entered, and in fact, raced that same day on a different track.
In what was now essentially a match race, the advantage shifted to Man o' War, whose front-running style allowed him to dictate the pace. He was almost flat-footed at the break but quickly gathered speed to draw clear of Sir Barton in the first furlong. Kummer then slowed the pace while maintaining a two-length lead down the backstretch. On the final turn, Man o' War put in a brief spurt and quickly opened the lead to five lengths. Kummer again pulled him in and Man o' War maintained a steady pace to the wire to win by seven lengths in a "ridiculously easy" fashion. Although the time of 2:03 was well off the American record shared by Man o' War and Sir Barton, it still broke the track record by over six seconds. Man o' War's share of the purse made him the highest-earning horse in American history. The gold trophy presented in the winner's circle, designed by Tiffany & Co, was later donated by Mrs. Riddle to Saratoga and is now used as the trophy for the Travers Stakes.
There were no formal awards for American Horse of the Year at the time, but Man o' War was informally acknowledged as such in a retroactive poll of turf writers. In its summary of the sporting year, The New York Times stated, "A superman (Babe Ruth) and a superhorse – these were sport's greatest contributions to the history of the year about to close. Some might rate the superhorse, Man o' War, as the outstanding figure of the two, for he has passed on from the field of competition and has left a story of achievement which may never be surpassed."
Over his two-year career, Man o' War won 20 of 21 races, setting three world records, two American records, and three track records.