Tokyo matchup one for the books

History will be made at Tokyo Racecourse on Sunday when three Japanese Derby winners - Deep Sky, Vodka, and Meisho Samson - meet in the Japan Cup. The only other time three national derby winners ran in the same race was in 1917, when Kentucky Derby winners Regret, Old Rosebud, and Omar Khayyam faced off in a memorable Brooklyn Handicap at the old Aqueduct Racetrack.

In an era when most of the best horses in America were trained in New York, the 1 1/8-mile Brooklyn Handicap was one of the country's most important races, and one that provided 3-year-olds with a late-June opportunity to meet the older generation. The 1917 renewal was so good, it rates a strong argument as the winner of the mythical "Race of the Century" award.

The legendary Regret, the first filly to win the Kentucky Derby in 1915, was saddled with 122 pounds in the Brooklyn, but owner Henry Payne Whitney and trainer James Rowe were not concerned, even though the New Jersey-bred mare was spotting the 1914 Derby winner, Old Rosebud, two pounds, and the 1917 Derby winner, Omar Khayyam, seven pounds. Even the presence of the 1914 Horse of the Year and 1915-1916 champion older horse, Roamer, could not dent the optimism of Regret's connections.

Regret, as was her wont, went straight to the front under Joe Notter and appeared to be the winner entering the stretch when cruel fate played its hand. Closing on the outside came the unheralded Borrow, a 9-year-old gelding who was, ironically, owned by Whitney and trained Rowe. Despite every effort by Notter to keep Regret on the lead, Borrow and his rider, Bill Knapp, got up on the line to win by a nose. Old Rosebud came home third, while Omar Khayyam trailed in last as Borrow set an American record of 1:49.40 for 1 1/8 miles. Whitney was later seen weeping in the winners' circle, not for joy at having won with Borrow, but for grief at Regret's defeat.

Many handicappers at the time considered Regret's narrow loss to be the best performance of her storied career. A further measure of the quality of the 1917 Brooklyn Handicap can be found in The Blood-Horse's list of the top 100 racehorses of the 20th century, on which Regret is rated 71st, Old Rosebud 88th, and Roamer 99th.

This year's Japan Cup contains a parallel to the 1917 Brooklyn in the filly Vodka, who in 2007 became the first of her sex to win the Japanese Derby since 1943. Like Regret in her time, Vodka is her nation's most popular racehorse. Unlike Regret, she will not be opposed by a longshot stablemate who might cause her owner, Yasunari Tanimizu, to shed anything but tears of joy should she win on Sunday.