Earlier in the week, I went over the opposite: the five best Kentucky Derby winners to come back and lose the Preakness Stakes. There were some good horses, including champion filly Genuine Risk and Secretariat's stable-mate Riva Ridge.
But this list is much more packed.
The distance, field size and even luck of the Derby make it a much more difficult jewel to conquer. Many great horses have failed to find the wire first on the first Saturday in May, yet still went on to become absolute legends of the sport.
Or more succinctly, the list of Preakness winners is a bit more accomplished than the list of Kentucky Derby winners.
Looking just since World War II, here are the five best horses that ran in the Kentucky Derby and lost but came back and claimed the Preakness.
(Please note that most old Preaknesses are not on YouTube, so I've attached video of the Kentucky Derby when the Preakness is unavailable)
A record pace got to Point Given in the 2001 Kentucky Derby, a remarkable 44 4/5 seconds for the opening half-mile, threw the race into pandemonium. Monarchos came away with the Roses while Point Given failed to finish in the top two for the only time in his career. The Bob Baffert colt was a shocking fifth.
But in the Preakness, Point Given was much the best, strolling home to a comfortable win. He was even more impressive in the Belmont, storming home to victory by more than a dozen lengths, becoming the first horse since Tabasco Cat in 1994 to take both the Preakness and the Belmont.
That summer, he followed up his two Classic wins with the two big Summer Derbies, the Haskell Invitational at Monmouth and the Travers Stakes at Saratoga.
Unfortunately, that would be his last start, as a tendon injury forced his retirement before he had a chance to battle reigning Breeders' Cup Classic winner Tiznow or European invader Sakhee in the Classic.
And sorry about the fact that there is no English-language 2001 Preakness on YouTube.
Here's a Preakness that I forgot about when making my list of the 10 greatest Preaknesses.
In the Kentucky Derby, Street Sense beat Hard Spun after cutting off Hard Spun at the top of the stretch. Curlin ran third as the second-choice after Street Sense. I know I'm in the minority on this, but it is one of the greatest shames in the history of the Kentucky Derby that there was no inquiry into the running of the Derby. Hard Spun clearly buckled his run and was re-catching Street Sense at the wire.
But that's irrelevant.
Curlin was beat, and boy did he come back.
He nipped Street Sense at the wire to win the Preakness, before Rags and Riches held him off through the entirety of the Belmont stretch three weeks later.
But after losing the Haskell, Curlin would win all seven of his remaining starts on dirt tracks, including the 2007 Breeders' Cup Classic over Horse of the Year candidates Hard Spun and Lawyer Ron and the 2008 Dubai World Cup.
A repeat in the 2008 Jockey Club Gold Cup made Curlin the first US-based horse to top $10 million in career earnings.
And in January 2009, he became the first horse to win a second consecutive Eclipse Award as North American Horse of the Year since Affirmed.
Unlike the two horses ahead of him on this list, Damascus wasn't a champion at two. He won three of four starts, but a limited campaign left much of his potential unrealized that fall. However, at three, he did win the Wood Memorial to establish himself as the favorite before the Run for the Roses.
Yet he ran a beaten third on the first Saturday in May, losing to long-shot Proud Clarion after getting spooked by the crowd.
Given a stable pony named Duffy and a rooster named Pete to calm him, Damascus shipped into Pimlico on the day of the Preakness and won. The charm continued to work, and Damascus went on to claim one of the greatest summers in the annals of American racing.
Belmont Park was closed through the mid-1960s due to renovations, so Damascus had to go to Aqueduct to win the Belmont Stakes.
He won the Travers, the mid-summer Derby, by an outrageous 22 lengths, sweeping his way to the top of the Horse of the Year debate.
Finally, in October, the top three horses met at Aqueduct for the Woodward. Four-year-old Buckpasser and fellow three-year-old Dr. Fager were both poised to wrestle Horse of the Year away from Damascus, but a lightning pace got to the field and it was Damascus who ran away for a 10-length triumph.
Damascus was Horse of the Year.
If you want to feel bad for Buckpasser or Dr. Fager, don't. Buckpasser was Horse of the Year in 1966 and Dr. Fager won the honor in 1968. Not every day you have three champions battle in one race.
Along with Misty Morn and Bold Ruler, Nashua was amongst the last great horses trained by Sunny Jim Fitzsimmons in his 80 years in the sport.
He was the champion two-year-old in 1954 and started 1955 strongly. He took the two big Florida prep races, the Florida Derby and Flamingo Stakes, before shipping to New York and winning the Wood Memorial.
But he couldn't catch Swaps in the Kentucky Derby, suffering defeat in America's biggest race.
Unluckily for race fans, Swaps was not nominated to either the Preakness of Belmont Stakes, leaving Nashua as the only great horse to run in those two. And of course, he won them both.
His Preakness win shattered more than a second of the Pimlico track record for 1 3/16 miles and established Nashua as the best of the division. His nine-length score in the Belmont only elevated him some more.
That summer, he finally met Swaps again in a much-anticipated match race at Chicago's Washington Park. He blew away the Derby winner to a resounding six-length triumph, getting the upper hand in the second and final meeting between the two.
He set a single-season record for earnings and earned a deserved Horse of the Year honor.
At four, Nashua went on to become the first horse sold for $1 million and just the second horse to pass the $1-million mark in earnings. He then went on to break Citation's earnings mark.
In the final start of his career, Nashua broke the national record for a two-mile race on the dirt, winning the Jockey Club Gold Cup at Belmont in 3:20 2/5.
This was an easy choice.
Native Dancer is, by a large margin, the best horse ever to lose the Kentucky Derby.
In 22 lifetime starts, he only lost once, and that was by an ever-diminishing head to Dark Star in the 1953 Kentucky Derby. Dark Star peaked on the correct day; Native Dancer didn't.
But before and after the Kentucky Derby, the Dancer was one of the greatest horses turf had ever seen.
He swept through his two-year-old season, winning all nine starts, on his way to Horse of the Year honors. Only three juveniles since him, including Secretariat, have been awarded Horse of the Year.
As a three-year-old, he won the Gotham Mile and Wood Memorial Stakes to lead up to the Derby. After the shock defeat, he won the Dwyer Stakes before holding off Jamie K to win the Preakness. The Belmont and Travers followed in easy order.
After recording his most impressive win, a stunning stretch drive from well back to somehow take the Met Mile in 1954, Native Dancer was set for a summer campaign towards a fall appearance in France in the Prix de l'Arc de Triomphe.
But it was not to be.
He was retired that August after injuring his leg for a second time. Despite racing only three times at four, he won his second Horse of the Year award.