World history would make the 1940s as the decade of war, starting with the Nazi invasion of Poland in September 1939 and ending with the descent into a conflict that left the planet cold with fear at times. On the racetrack, the decade was one of Triple Crown winners – four in total, the most of any decade so far – yet those years were rich with great performances, a long list of great horses vying for the hearts and minds of the fans that stood trackside.

On that list are three outstanding fillies who came from barns that dominated the sport at its highest levels, leading their divisions while stepping into open company and making their mark there as well.

Vagrancy (1939-1964)

That her sire had already produced one Triple Crown winner would have been enough to give William Woodward high hopes about his filly by Sir Gallahad III. That her damsire was Man o’ War made Vagrancy’s success on the racetrack almost a given. Add to those advantages her dam’s success as a broodmare, then the tall dark bay filly’s success in both phases of her life taps her as a name any racing fan should know.

Vagrancy (Keeneland Library/Meadors Collection)

At 16 hands, 1¼ inches, Vagrancy raced in the white with red polka dots of Belair Stud, trained by Hall of Fame trainer “Sunny Jim” Fitzsimmons and ridden by another Hall of Famer, Jimmy Stout, in most of her starts. With that pedigree and those connections, she had every advantage behind her, and she rose to the occasion.

At 2, she was brought along slowly as Fitzsimmons was wont to do, starting only eight times and winning three of those. Her best stakes showing that first season was a third in the Selima Stakes at Laurel Park, but that was just the first scene in the show to come.

Like most horses of her size, Vagrancy needed time to grow into her frame and needed her 2-year-old season to lay the foundation for what 1942 would bring. By season’s end, the only horse that had more victories than her was Whirlaway, who had 12 to her 11. She notched her first stakes win in the Pimlico Oaks before going on to finish second in the Acorn. Her next stakes win was one William Woodward cherished, a two-length victory in the Coaching Club American Oaks, named for the club that the master of Belair was a member. From there, she added wins in many of the distaff features familiar to 21^st century fans: the Beldame and Ladies Handicaps; the Delaware Oaks; and the Gazelle and Alabama Stakes.

She did venture out of her division at 3, finishing second to Alsab in the 1⅝-mile Lawrence Realization and fourth in races like the Empire City, Butler, and Maryland Handicaps. In all, Vagrancy raced 21 times in 1942, her 11 wins netting her nearly $85,000 in purses and earning her the title of champion 3-year-old filly and champion handicap female for the year.

While Woodward opted to race her at 4, chasing the $100,000 mark for her career earnings, she was not quite the same that following year. She finished in the money in the Beldame, Ladies, and Diana Handicaps, but added no more stakes wins to her tally of 15 wins in 42 starts and $102,480 in purse earnings. She retired to Claiborne Farm where she joined the Belair broodmare band, producing eight foals for Woodward.

Of those eight, the first was Black Tarquin, a colt by Rhodes Scholar foaled at Claiborne Farm but imported to England to join Woodward’s English stable. He won the St. Leger, the last jewel of the English Triple Crown, and was second in the 1949 Ascot Gold Cup as well. His quality defined what Vagrancy was as a racehorse and a broodmare: a champion who fulfilled the promise of her purple pedigree and then passed on that quality to the next generation.

Wistful (1946-1964)

In the 1930s, the white with red polka dots had been ubiquitous on American racetracks. Seen on two Triple Crown winners, the success that William Woodward’s stable had that decade presaged what was to come in the 1940s. From Whirlaway to Citation, Calumet Farm churned out champions at a rate comparable to that of Belair into the 1950s and 1960s.

Wistful winning the Ben Ali Handicap at Keeneland. (Keeneland Library/Meadors Collection)

In the same year that Citation was foaled, the Calumet mare Easy Lass produced another son by Bull Lea, the stalwart second fiddle named Coaltown. The following year, she foaled Wistful, a chestnut filly by the good Calumet sire Sun Again. Like her half-brother, she was plagued by chronic ankle issues, which very likely accounts for her limited 2-year-old season. Wistful started only two times in 1948 and broke her maiden in the second start. Because of her late start, she had a limited winter break and posted her first start at 3 in mid-January. Her first stakes win, though, was still a few months off.

Wistful picked a fortuitous time to break her stakes maiden, though. The day after Ponder won the Kentucky Derby in the Calumet red and blue, the daughter of Easy Lass made it a Derby-Oaks double for the Wrights, taking the Kentucky Oaks by 4½ lengths. She followed that up with a win a week later in the Pimlico Oaks and then 15 days after that with a half-length victory in the Coaching Club American Oaks, earning Wistful something akin to an unofficial filly Triple Crown. She finished her 3-year-old season as co-champion of her division alongside stablemate Two Lea.

The Calumet filly raced one more time in 1949 and then ran into more issues with her ankles that sidelined her until the next year. Over the next three seasons, Wistful was less consistent but still managed to win the Clark, Beverly, and Ben Ali Handicaps before her retirement. As a broodmare, she produced only three foals, including General Duke, who won the 1957 Florida Derby.

Two Lea and Wistful were but two names on a long list of champion fillies for Calumet Farm, a list headed by another stellar distaff racer named Twilight Tear.

Twilight Tear (1941-1954)

Warren Wright was betting on Bull Lea continuing his success on the racetrack into his years in the breeding shed. During his three seasons on the track, Bull Lea’s list of wins featured the Bluegrass Stakes and the Widener Handicap with a pedigree that complimented his ability. His sire, Bull Dog, was a full-brother to Sir Gallahad III, sire of Gallant Fox among others, and his dam, Rose Leaves, produced several stakes winners in addition to Bull Lea. By the time he went to stud, Wright’s conversion of Calumet from Standardbreds to Thoroughbreds was fully complete, with a view toward breeding the horses they would race. His cross of Bull Lea with Lady Lark, a Blue Larkspur mare, produced a beautiful bay filly with one hind sock, a lady named Twilight Tear.

Calumet Silks

She was a winner on debut and followed that up with her first stakes win in only her second start, taking the Arlington Lassie by 2½ lengths. Twilight Tear would round out her 2-year-old season with two more wins and a second in the Selima Stakes, a nice start to what would become a Hall of Fame career.

Considered one of Calumet’s early Derby hopefuls, the filly opened her 3-year-old season in a surprising spot: against older horses in the Leap Year Handicap at Hialeah on Feb. 29, Leap Day. She carried the race’s lightest weight, 101 pounds, and finished a strong third, just two lengths behind the winner. She followed that up with 16 more starts in 1944. She bypassed the Derby, won by stablemate Pensive, and instead targeted the distaff division’s big sophomore races like the Pimlico Oaks, the Acorn, and the Coaching Club American Oaks. With her domination of the filly division complete with clear victories in all three races, trainer Ben Jones showed his confidence in her abilities by sending her against the boys again.

Before that trio of wins, she beat colts in the Rennert Handicap at Pimlico before winning the Pimlico Oaks a week later. Then she set a track record for seven furlongs in the Skokie Handicap at Washington Park near Chicago and beat Pensive and other colts with ease. Next, she moved on to the Classic Stakes, a 3-year-old feature won by horses like Gallant Fox and Omaha, and again beat the boys with ease, taking the lead out of the gate and never looking back. After a second in the Alabama broke her streak of wins in her division, Twilight Tear won twice more before running into a muddy track in the Maryland Handicap. She carried 130 pounds and labored through the 1 ¼-mile race to finish fourth.

To round out 1944, Twilight Tears connections accepted an invitation to contest the Pimlico Special on Nov. 1, where she would meet a formidable Devil Diver. The Greentree Stable star had won his second of three Metropolitan Handicaps already that year and added the Whitney to his long list of victories. For the 1 3/16-mile Pimlico Special, he carried 126 pounds to Twilight Tear’s 117, but it was not weight that made the difference. Rather, it was the filly’s speed out of the gate. She broke fast and took the lead immediately under jockey Doug Dodson. Neither Devil Diver nor Megogo was able to gain on the Calumet filly and were well back at the finish.

Twilight Tear’s 1944 season earned her both Horse of the Year and champion 3-year-old filly honors. As she counted down to the start of her 4-year-old season in 1945, World War II intervened: James F. Byrnes, director of the country’s war mobilization efforts, suspended racing until May 1945 as the Allies ramped up their efforts to end the war on the European front. Ahead of her first start, the filly bled in a workout and was sidelined until late August. In her one and only start at 4, she bled again and was promptly retired to Calumet Farm where she joined their storied broodmare band.

Nearly seven decades after her death in 1954, Twilight Tear lives on in the form of a World War II era P-51 Mustang. Flown by Lieutenant Hubert Davis during the later years of the conflict in Europe, Twilight Tear flew 35 combat missions and shot down three enemy aircraft during her time in the air. Fully restored in 2007, the plane named for this Horse of the Year keeps the name Twilight Tear flying at airshows, the restored aircraft thrilling crowds as the Calumet star did in the 1940s.