Shackleford lived up to expectations when he won the 2011 Preakness Stakes. (Photos by Eclipse Sportswire)
When Shackleford stepped into a starting gate for the first time in 2010, the flashy chestnut had a lot to live up to. He was the first colt out of Oatsee, a mare with blue hen potential who had already produced the Grade 1 Alabama Stakes winner Lady Joanne.
After running a forgettable ninth on Keeneland's synthetic Polytrack surface, Shackleford would accomplish more during his racing career than anything Lady Joanne achieved on the track.
Shackleford reeled off two straight dirt victories before entering the Fountain of Youth Stakes. While that race didn’t go to plan with Shackleford finishing fifth, he bounced back to finish second by only a head in the Florida Derby after leading at every call before the finish.
The colt came close to becoming the 137th Kentucky Derby winner in 2011, once again leading at nearly every call. But he was passed in the final furlong and faded to fourth. But two weeks later, Shackleford got his revenge.
After getting worked up before the race some people wrote Shackleford off, but his trainer Dale Romans wasn’t worried. Settling into second soon after the start, he was only a half-length behind Flashpoint most of the way around the track. Going into the far turn, Jesus Castanon unleashed Shackleford and they shot to the lead. A late charge by Kentucky Derby winner Animal Kingdom had Shackleford fans holding their breath, but the Derby winner was too late and Shackleford added a classic win to his résumé.
THE 2011 PREAKNESS STAKES
“He wasn't acting that bad. It's a hot day, so that wasn't worrying me too much. I was more concerned at the quarter-pole if he was going to hold on,” Romans told NBC Sports Network after the race. “I've won some big races, but none as exciting as that one.”
Shackleford completed the Triple Crown trail by finishing fifth in the Belmont Stakes after leading into the stretch.
While Shackleford didn’t see the winner’s circle again as a 3-year-old, he was second in three of his four remaining races that year, including the Breeders’ Cup Dirt Mile. He ended his season as a finalist for the Eclipse Award as champion 3-year-old male with more than $1.9-million in earnings.
Returning as a 4-year-old, Shackleford needed a couple of races to regain his top form. But returning to Churchill Downs on Kentucky Derby day, Shackleford thrilled Derby fans in the Churchill Down Stakes on the undercard. While he only won the race by a length, he beat 2011 Breeders’ Cup Sprint winner Amazombie.
Next up was the Met Mile, a rematch between Shackleford and Caleb’s Posse. The pair had faced off three times previously with Caleb’s Posse finishing ahead of Shackleford twice. The race looked like it was going to mirror the previous year’s Breeders’ Cup Dirt Mile with Shackleford on the lead in the stretch and Caleb’s Posse quickly closing. It came down to a nose bob but a determined Shackleford earned the victory, giving him the distinction of winning a Grade 1 in two of his three years on the track.
THE 2012 MET MILE
That August, Shackleford appeared at Saratoga Race Course in the Alfred G. Vanderbilt Handicap. The colt had not run well at the Spa when finishing eighth in the 2011 Travers Stakes and this time he also faced muddy conditions. This proved to be his undoing as he never made the lead and finished last.
“The first two jumps, I knew right away. He jumped out of there, he didn’t grab onto the bit. I put him into the race, and he did not want to go there,” jockey John Velazquez said.
“As I gave him his head again to try to put him into the race again, he let go right away. He was not comfortable. Seeing the way he’d run on a wet [track previously], I was a little bit concerned … and he proved today, I guess, that he doesn’t like it.”
After finishing second in a prep race, Shackleford took his show on the road for the 2012 Breeders’ Cup Dirt Mile, racing west of the Mississippi for the first time.
Looking to better his second-place finish the year before, Shackleford loaded into the gate as the co-favorite in the race. But a bobble at the start of the race cost him all chance of getting to the lead quickly. While he was in third a half-mile into the race, he finished seventh.
Shackleford was given a chance to end his career in style when he was entered in the Grade 1 Clark Handicap later that November. Reunited with Castanon, who hadn’t had the mount since May, Shackleford went straight to the lead. It was easy to see that the colt was in command of the race all the way around the track as he comfortably galloped through easy fractions. Take Charge Indy attempted to challenge Shackleford in the stretch but with another spurt of speed, Shackleford pulled away to win by a length in his career finale.
“That’s the way he’s supposed to leave,” Romans said. “He was very impressive today. That’s ‘Shack’ at his best. That’s how we expected him to run in the Breeders’ Cup [Dirt Mile], and it wasn’t his fault that he stumbled. That’s the way I wanted to see him end his career. I’m very proud of him. This win was for him. It put him back in the winner’s circle before he left and let everyone know he’s still the same Shackleford he used to be.”
The win brought his career earnings up to $3,090,101 with six wins in 20 starts, including three Grade 1 victories. He finished on the board 12 times and was again named an Eclipse Award finalist in 2012, this time in the male sprinter category.
SHACKLEFORD LEAVES THE WINNER'S CIRCLE FOR THE LAST TIME AFTER THE CLARK
Shackleford retired to Darby Dan Farm in 2013, quickly settling in to his new routine as a stallion.
“Shackleford has definitely taken to his new career,” said Ryan Norton, Darby Dan’s stallion manager. “He has settled in very nicely and has been a complete gentleman. He is the stallion we use on all our tours, not only because of his popularity but his demeanor. ‘Shack’ has no problem letting tourists stand beside them and have their picture taken.”
A popular horse on the track, he has become Darby Dan’s most popular stallion. Inspired by Shackleford, a group of his fans leased a broodmare to breed to the stallion with the resulting filly born on Kentucky Oaks day this year. Fans also visit Shackleford on his birthday, bringing him presents, and send him Valentine’s Day and Christmas cards.
But fans aren’t the only ones who find him popular, with breeders sending him more than 100 mares in each of his two years at stud.
“Breeders have supported Shackleford in the first two years,” Norton said “He bred 168 mares in his first season and is scheduled to breed 120 mares this year. There was no denying that Shackleford had heart, and I think breeders remember how gutsy he was on the track. It also doesn't hurt that he is out of  Broodmare of the Year Oatsee, and he was an extremely fast horse that could carry that speed over the classic distances.”
Shackleford has played a big part in helping Darby Dan add to a long and successful history in the industry. Considered the farm’s anchor stallion, Norton believes Shackleford has boosted the farm’s reputation and that the sky is the limit for his budding career.
“Like any farm that stands stallions, you are always the optimist and believe every stallion we stand will be the ‘next big thing.’ With the number of quality mares he has bred his first two years and the consistently nice foals he has had so far, I believe the sky is the limit and there is no reason why Shackleford, down the road, could not be the next Tapit or War Front,” he said.
Shackleford’s first foals were born this year and will be hitting the sales in the fall. It will be a few years until it’s known if Shackleford is passing on his heart and talent, but it’s clear that so far he’s lived up to the high expectations placed upon him before he ever hit the track.