‘I knew he was something special’ – why Cigar is still the invincible one for Jerry Bailey

Horse Racing Cigar
A legend in the making: Cigar wins the NYRA (now Cigar) Mile at Aqueduct in 1994. Photo: NYRA

On the eve of the G1 Cigar Mile at Aqueduct, Ryan Martin (NYRA) talks to legendary jockey Jerry Bailey about his memories of one of the greatest performers in the modern era of US racing

USA: When Cigar won 16 straight races against the best horses of his generation, tying the all-time win streak set by Citation, Allan Paulson’s Hall of Famer was cemented as an all-time great.

A total of 11 G1 victories across six racetracks, a perfect 1995 season with ten victories and a record-breaking lifetime bankroll of $9,999,815 highlight Cigar’s CV as one of the most noteworthy horses in North American racing history.

But the collection of trophies wasn’t the primary factor in garlanded rider Jerry Bailey forming such a close bond with the dual Horse of the Year, who first rose to prominence with his victory in the NYRA Mile at Aqueduct in 1994. The 2020 edition of the G1 contest, now named in honour of Cigar, takes place on Saturday [Dec 5].

‘He was just so cool’

“It was his personality – he was just so cool,” says Bailey, 63. “Early on after his first two or three races, I knew he was something special.”

Bailey was a household name in the racing world before Cigar’s flawless 1995 campaign, having ridden for 19 years at that point. A 56-time G1-winning rider before becoming Cigar’s regular jockey, Bailey had piloted 1993 Kentucky Derby winner Sea Hero and the 1991 Preakness and Belmont winner Hansel.

Yet Bailey’s connection with Cigar was not what one might imagine. In his words, it was very similar to the relationship between a doctor and a patient.

“It was difficult to form relationships with the horses, because you either get taken off a horse or take off to ride a different horse,” Bailey explains. 

“There were few long-lasting relationships with the horses, so it was hard to have close relationships with them. That’s how I looked at it. I liked horses a lot, but I didn’t have relationships with them. I would go to work, do my job, ride the horses and then go home.”

But along came Cigar – and Bailey found a new love and appreciation for the horse. It took a while for the legend to grow, however.

Horse Racing Jerry Bailey and Cigar
Legendary partnership: Cigar and Jerry Bailey after their ground-breaking victory in the inaugural Dubai World Cup in March 1996.

Cigar broke his maiden on dirt at Hollywood Park in May 1993 for west coast-based trainer Alex Hassinger but raced on grass for his next seven starts. He was then transferred to Hall of Fame trainer Bill Mott, who gave Bailey the leg-up in Cigar’s third start for new connections, when he finished seventh on the grass in September 1994 at Belmont Park.

‘Bill Mott thought he was a better horse than he was showing’

Julie Krone and Mike Smith had a turn aboard Cigar for his next two starts before Bailey returned. “It was a case of musical jockeys,” Bailey says. “We all knew Bill thought that he was a better horse than he was showing.”

Cigar made a triumphant return to dirt under Smith in October 1994 for a 104 Beyer Speed Figure going a one-turn mile at Aqueduct. It would be the last time Cigar would race without Bailey on his back.

“I was riding at the Meadowlands that night when Mike called me up and said, ‘He ran off the TV screen’,” Bailey recalls. “Mike had committed to riding Devil His Due in the NYRA Mile. 

“Ten days to two weeks before the they took entries for the race, I called up my agent [Bob Freize] and said: ‘Make sure you talk to Bill Mott and tell him that we’re available.’ He won the NYRA Mile and that performance confirmed what Mike said to be true.”

Cigar strolled home a seven-length winner over Devil His Due before picking up where he left off in January 1995 with a Gulfstream allowance before a 2½-length score in the G1 Donn Handicap.

After another Gulfstream Park triumph in the track’s G1 namesake race, Cigar took his show on the road, winning five more G1s over four different tracks. The ultimate test awaited Cigar in the year-end Grade 1 Breeders’ Cup Classic, where he would put an 11-race win streak on the line over his home track of Belmont Park.

There were still several obstacles against him, however. He drew post 10 in the 11-horse field, which included accomplished runners Unaccounted For, Star Standard, defending champion Concern, Tinners Way, as well as a G1 winner from Europe in Godolphin’s Halling. 

‘My fingers were completely numb’

Cigar was also asked to contest over a muddy main track for the first time. He broke sharply from his outside post, Bailey allowing him to stride out to secure a favourable position. “From the ten post, I had to let him run a little bit to be four wide and not seven wide,” Bailey says.

Yet while Bailey wanted to save ground, Cigar had different plans. Bailey tried as hard as he could to keep him in behind horses, but Cigar was moving so aggressively that he had no choice but to let him make a premature move around the far turn. 

“The feeling was going out of my fingers, they were completely numb. He was pulling that hard,” Bailey explains. “From the gate, he had the idea, ‘You said go, now let’s go’. I saw Unaccounted For and just like that he went from the four-path to the rail.

“He beat most horses by the time the field approached the far turn,” adds Bailey, who retired in January 2006 with 5,893 North American victories to his name. “When you’re out on the track, you just know. They were struggling to keep up and my horse is going 80 per cent. 

“Most horses he ran against he had beat by the time they got to the far turn. He was just so good and so talented. He had a high cruising speed. He wanted to be on the lead in every jump of the race and every point of call. He was basically a brilliant miler that Bill got to go a mile and a quarter.”

‘The unconquerable, invincible, unbeatable Cigar’

Cigar proved victorious by 2½ lengths over L’Carriere in the Breeders’ Cup Classic and was dubbed by NYRA track announcer Tom Durkin as the “unconquerable, invincible, unbeatable Cigar” in one of the most iconic race calls of all time.

With 1995 Horse of the Year honors wrapped up, Cigar proved himself the best horse in the country. But Cigar was much more than that for Bailey. The newly minted Hall of Fame jockey found himself going above and beyond the ‘doctor-patient’ type of relationship he had with previous horses, even taking his three-year-old son Justin to visit the champion the morning after the Classic.

“I wanted to spend as much time with him as I could,” says Bailey, now a hugely respected NBC Sports racing analyst. “I would go back to the barn just to be around him and just to watch him graze. I took Justin back to the barn the morning after and that was a special moment. He was so gentle and calm when he wasn’t on the track.”

Despite the perfect 10-for-10 season, there were still some who doubted Cigar.

“There were naysayers,” Bailey says. “Some people thought, ‘Okay, Cigar is legit, but what happens when another horse looks him in the eye?’”

Cigar answered that question with authority when he travelled to the Middle East for the inaugural running of the $4 million Dubai World Cup after an interrupted preparation in March 1996. Cigar established clear command at the top of the stretch, but Soul Of The Matter loomed large and powered his way to even terms.

Bailey said he wasn’t fazed. “I was trying to save as much as I could for as long as I could,” he says. “When Soul Of The Matter came right up to Cigar, I was still in reserve mode.

“I could feel that motor get going again. I knew that he might get by me, but he wasn’t going to beat me. He might have gotten a head in front of me for a jump or two, but I could feel Cigar re-engaging and I knew he had enough to do it.”

After a repeat win in the Massachusetts Handicap and a 3 ½-length victory in the specially-designed Arlington Citation Challenge, Cigar tied the 16 consecutive win record of 1948 Triple Crown winner Citation. 

A memorable run came to an end after shipping to California for the G1 Pacific Classic when second to longshot Dare And Go. “At that point, he had some miles in him – he went from Florida, to Dubai, to Massachusetts, to Chicago and now Del Mar,” Bailey says.

He explains that his plan in the Pacific Classic was to keep Cigar in striking range to that year’s G1 Hollywood Gold Cup winner Siphon, who was sure to be the pacesetter. But it was a little too close for comfort as Cigar gave way in mid-stretch, thus putting an end to his winning streak.

“I asked him more than he could do,” Bailey says. “For the next two to three years, I ran that race in my mind a hundred times a year.

“I rode a horse named Geri for Mott and Paulson in the Hollywood Gold Cup that year and lost to Siphon. Siphon got away early that day and it was my intention to not let him get away. In the Pacific Classic, Corey Nakatani was on Dramatic Gold and he was intent on trying to lock me in behind Siphon. I thought that at some point he would back off, but he didn’t.”

‘There wasn’t a situation he couldn’t get you out of’

Even 25 years later, Cigar holds the highest sentimental value of any horse Bailey has ridden throughout his 30-year career.

“I wasn’t ever really all that nervous when I was on him before a race because he was just that good,” he says. “Not only was he good, he was consistent. His style of running was the most you could ask for. 

“He had great speed, acceleration, and there wasn’t a situation in a race that he couldn’t get you out of. He had so many tools and gears. Good horses can win over broken glass and he didn’t care. I don’t think he liked Suffolk all that well, but he still won over the surface twice.”

When Cigar retired at the end of 1996 following a third to Alphabet Soup in the Breeders’ Cup Classic at Woodbine, Bailey had piloted the horse to 16 of his 19 lifetime victories.

But what resonated the most for Bailey was Cigar’s gentle demeanor around the barn. “The only other horse I’ve seen that was like that was American Pharoah,” Bailey says. “He loved being showed off and being with people.”

After proving infertile as a stallion, Cigar spent the rest of his days being shown off to fans visiting the Hall of Champions at the Kentucky Horse Park, where he was stabled alongside John Henry and Da Hoss until he died in October 2014 at the age of 24.

“There really was no one else like him,” Bailey says.

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