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DellaRocca 1995 Cigar Woodward.jpg

Cigar, Jerry Bailey up (NYRA photo)
Induction Year: 
Allen E. Paulson
Allen E. Paulson and Madeleine Paulson
Alex Hassinger, Jr., Bill Mott
Palace Music
Solar Slew
Seattle Slew
Career Years: 

Tab Wrapper


Named after a navigational intersection for airplanes by aerospace magnate Allen Paulson, Cigar was foaled at Country Life Farm near Bel Air, Md. After enjoying modest success early in his career, Cigar won back-to-back Horse of the Year awards, compiled a 16-race win streak and retired with the all-time record for purse earnings in North America.


Arriving at the races in 1993 as a 3-year-old with trainer Alex Hassinger, Jr., Cigar broke his maiden in his second career start at Hollywood Park. His other accomplishments that year were minor, as he finished second in the Grade 3 Volante Handicap at Santa Anita and third in the Grade 3 Ascot Handicap at Bay Meadows. He finished 11th in his final start of the year, the Hollywood Derby.


Sent to trainer Bill Mott and shipped to the East Coast as a 4-year-old, Cigar did not finish better than third in his first four starts with Mott. However, he won an allowance race at Aqueduct in late October of 1994 by eight lengths that began a remarkable stretch of almost two years during which Cigar was unbeatable.


Cigar’s first breakthrough victory was in the 1994 NYRA Mile, a Grade 1 event. With Jerry Bailey in the irons, Cigar drew off to defeat Devil His Due by seven lengths. It was Cigar’s final start of the year, but just the beginning of a remarkable journey.


In 1995, at age 5, Cigar won all 10 of his starts and earned $4,819,800. He won eight Grade 1 races year: the Donn Handicap, Gulfstream Park Handicap, Oaklawn Handicap, Pimlico Special Handicap, Hollywood Gold Cup, Woodward Stakes, Jockey Club Gold Cup and Breeders’ Cup Classic. The undefeated season also included a win in the Massachusetts Handicap and an allowance score at Gulfstream. Cigar set a stakes record with his victory in the Breeders’ Cup Classic, coving 1¼ miles at Belmont Park in 1:59.58.  


Returning as a 6-year-old, Cigar repeated in the Donn Handicap before traveling overseas to win the inaugural Dubai World Cup. He then returned to America to repeat in the Massachusetts Handicap before a record crowd at Suffolk Downs to stretch his win streak to 15.


Next up, Arlington Park carded a special race, the Arlington Citation Challenge Invitational, for Cigar to attempt to match the modern-day win streak of 16 set by Triple Crown winner Citation. Carrying 130 pounds, Cigar pulled away for his record-tying 16th consecutive win. In the process, he raised his season earnings to $4,578,454 to surpass Alysheba’s all-time record for a single season.


A record crowd of more than 40,000 showed up at Del Mar a month later as Cigar looked to break Citation’s record in the Pacific Classic, but Dare and Go passed Cigar in the stretch to win at odds of almost 40-1. Cigar bounced back to win the Woodward Stakes in his next start before finishing second in the Jockey Club Gold Cup and third in his final career start, the 1996 Breeders’ Cup Classic at Woodbine.  


Cigar was retired following the Breeders’ Cup Classic with a career record of 19-4-5 from 33 starts and record career earnings of $9,999,815, which was not surpassed until Curlin topped $10 million in 2008.


Cigar proved infertile as a stallion and lived out the remainder of his retirement at the Kentucky Horse Park’s Hall of Champions. He died Oct. 7, 2014 at the age of 24.


“He was the best of his generation and certainly the best horse I ever rode,” Bailey said.