Kentucky Derby Lucky Losers – Market Wise (1941)

Dec 17, 2025 Jennifer Kelly / TwinSpires.com

Market Wise, with Wendell Eads up, wins the McLennan Handicap. (Photo courtesy of the Keenleand Library / Credit to the Morgan Colection)

The 1941 Kentucky Derby featured Mr. Longtail, Whirlaway, the first of Calumet Farm’s eight winners and the first of their two Triple Crown winners, but that year’s Run for the Roses included another star in a colt named Market Wise. The son of a Kentucky Derby winner, this bay colt had more than one unique connection to America’s most famous race.

Though he would go on to make a name for himself in the handicap ranks, Market Wise rose from the claiming ranks to place in the 67th Kentucky Derby, earning the title of lucky loser with his prominent stakes wins at age three and beyond.

Shaky Start

Brokers Tip was the beneficiary of the raucous Fighting Finish in the 1933 Kentucky Derby. His jockey, Don Meade, battled Herb Fisher on Head Play down the stretch at Churchill Downs, the pair grabbing and whipping each other as their horses ran head-to-head over the last quarter of a mile. The stewards declared Brokers Tip the winner by a nose, giving the son of breeder/owner Edward R. Bradley’s Black Toney his lone victory in a 14-race career plagued by chronic unsoundness. When he was retired to stud, Bradley leased the stallion to Admiral Cary Travers Grayson, physician to three Presidents, who was also a long-time breeder and owner. He stood Brokers Tip at his Blue Ridge Stud in Virginia, where he covered one of Grayson’s own mares, On Hand.

As a racehorse, On Hand had finished third in her only career start, but her value was more in her pedigree than her performance. Her sire, On Watch, counted the great Colin as his own sire while her dam was a daughter of Hall of Famer Broomstick. When paired with Brokers Tip, the bay mare produced her third foal, a colt with splashes of white on his face and a front and rear ankle. Grayson passed away on Feb. 15, 1938, weeks before On Hand foaled on April 10. Grayson’s widow reserved the colt for the Saratoga yearling sale the following year, and the colt hammered down for $2,300 to Isabel Dodge Sloan’s Brookmeade Stable.

Market Wise (Photo courtesy of Keeneland Library / Credit to the Meadors Collection)

As a two-year-old in Sloane’s colors, Market Wise was, in a word, disappointing. In his first five starts, his best finish was sixth, trainer Hugh Fontaine dropping him into claiming company at one point, with no takers. Sloane made it known that the colt was for sale, and finally, word of that reached Louis Tufano, a New York-area contractor who was looking to get into owning racehorses. Along with his trainer, George W. Carroll, a former jockey, he struck a deal with Brookmeade to buy both Market Wise and another two-year-old, Flank, for $2,000.

In Tufano’s colors, the Brokers Tip colt finally broke his maiden in his seventh start, a one-mile, 70-yard maiden race with a $1,200 purse at Empire City. He won by 1 1/4 lengths, the victory nothing to shout about except for the money that Tufano and friends won on the colt, which more than paid for Market Wise. When the stable was transported south to Florida for the winter, Market Wise added one more win to his resume on Dec. 28. He exited his two-year-old season with a record of two wins in nine starts, but the son of a Derby winner was just getting started.

Upward Momentum

Carroll did not let the dust settle under Market Wise’s feet before he started his sophomore campaign. On Jan. 4, a week after his six-furlong allowance win, the colt followed that up with another victory in an allowance, prompting the trainer to try his charge in a stakes. Third in the Hialeah, Market Wise rewarded that performance with a fifth in the Bahamas before trying the Wood Memorial at Jamaica four starts and two wins later. With jockey Don Meade in the saddle, the same man who had ridden Brokers Tip to his Derby win, the Tufano colt ran down Curious Coin to win by a nose in the race’s final strides. That win was enough for Carroll to put the colt in the 1941 Kentucky Derby, where this underdog was about to face an immortal.

Behind the winning Whirlaway, Market Wise improved from midpack to third in the final furlongs of the 10-furlong classic, finishing just a neck back of second-place Staretor. Tufano’s colt met Whirlaway again in the Dwyer Stakes in late June after the Calumet colt had sealed his Triple Crown. Again, Whirlaway got the better of Market Wise, who was second by 1 1/4 lengths. The Dwyer was not the last time the pair would square off in 1941.

Inaugurated in 1919, the Jockey Club Gold Cup has an illustrious list of victors, including Man o’ War, Gallant Fox, and War Admiral. The 1941 edition had just four horses—Fenelon, Abbe Pierre, Market Wise, and Whirlaway—for the two-mile test. For the first 12 furlongs, Fenelon holds on to the lead, his time 2:28 4/5 for that distance, two-fifths off the American record. Jockey Basil James lay in wait until the far turn, waiting for Whirlaway to move before following suit. In a blink, Fenelon tires and the two three-year-olds take over, heads apart.

Market Wise with Basil James up with Whiraway and Alfred Robinson up in the Jockey Gold Cup at Belmont. (Photo courtesy of Keeneland Library / Credit to the Morgan Collection)

Whirlaway started to inch away from Market Wise, even putting a length between them, but the Tufano colt began to fight back. The crowd noise grew louder as the Triple Crown winner pulled away and then stilled as the upstart fought back. He creeps up on the Calumet champion, reaching his girth, his shoulder, his neck. At the wire, a photo finish; in the winner’s circle, Tufano, Carroll, and James, Market Wise, earning the victory by a nose.

The son of Brokers Tip rounded out his three-year-old season with wins in the Gallant Fox, the Governor Bowie Handicaps, and the Pimlico Special. His four- and five-year-old seasons saw more wins at the handicap level, taking the Suburban and Massachusetts Handicaps and the Narragansett Special among other stellar performances, which earned him a share of the 1943 Eclipse for Champion Handicap Male.

Market Wise with Basil James up winning the Suburban Handicap over Whirlaway with Eddie Arcaro up at Belmont. (Photo courtesy of Keeneland Library / Credit to the Morgan Collection)

He retired to Charles Asbury’s Hedgewood Farm, where he sired 150 foals, including 103 winners and four stakes winners, most notably To Market, who set a track record in winning the Massachusetts Handicap, a race that his sire also won.

Though Market Wise did not wear the roses in the 1941 Kentucky Derby, he built on the abilities his own Derby-winning sire imbued in him and crafted a noteworthy career that defied his shaky start, a Cinderella story for this lucky loser.