The fervor of the question increases with every passing year. And as the years turn into decades — three now and counting — the subject gets dissected so exhaustively that even those deemed experts abandon trying to come up with one concrete answer.
I'll Have Another's victories in the Kentucky Derby and Preakness Stakes have gathered the racing world to its latest roundtable discussion over why it has been 34 years since a horse has proven capable of capturing the three-race, five-week gauntlet that is the American Triple Crown.
Though just 11 legends have accomplished the feat, the current drought has long since passed the previous record 25-year gap between Citation's sweep in 1948 and Secretariat in 1973.
The one thought most agree upon is if I'll Have Another wins the Triple Crown, he'll have done so in an era unlike that of any of his predecessors.
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To merely say it takes a special horse to win the Triple Crown is too simple a way of explaining why a generation of fans exist who have never witnessed a sweep. Some of the greatest horses of our time, most notably Spectacular Bid (1979), Alysheba (1987) and Sunday Silence (1989), made it to this very point only to be tripped up by various factors during their 11/2-mile journeys around the Belmont oval.
For the majority of the 11 horses that have failed to finish the job since Affirmed did so in 1978, their attempts have come at a time when the racing landscape is drastically different than it was for the 11 who succeeded.
This is not your grandfather's racing. As the Thoroughbred breed has changed — for better or worse — so too have training styles and the attitude within the sport.
"I think it has (become harder to win) because of the reasons for which we breed horses," said Penny Chenery, owner of Secretariat. "Back in the '70s we were still breeding horses to race them, and so much of the industry now is concentrated on sales. So you breed a good-looking, early speed horse who isn't equipped to go a mile and a half, or to run three hard races in five weeks.
"We just have a different set of goals with the horses we breed now."
The Triple Crown races have not changed since the Thoroughbred Racing Association formally recognized the three-race series in 1950. The variables needed to notch victories in the trio, though, have grown to titanic proportions
Of the 11 Triple Crown winners, only the great War Admiral in 1937 began his run by defeating 19 others in the Kentucky Derby.
With the first leg now the most famous race in the sport and long-shot winners showing a Derby victor can come from anywhere, 19- and 20-horse fields have become the norm in the past decade, increasing the odds that even the most talented horse of a generation could be derailed by a troubled trip.
Though field sizes in general have declined over the years, the Triple Crown races regularly hit their starting-gate limits.
Citation only had to beat 15 total horses en route to his coronation. Secretariat defeated 21 others during his Triple Crown run. Seattle Slew and Affirmed faced 29 and 20 total rivals, respectively.
I'll Have Another took on 19 in the Derby, 10 in the Preakness and could encounter nine more foes in the Belmont
"It's not too tough to win the Triple Crown. It's just these fields are always full fields and it's all about getting a good trip," said Graham Motion, trainer of 2011 Kentucky Derby winner Animal Kingdom. "There is always going to be a horse in the Derby that's not going to get a good trip and that's what's going to make it so hard to have a Triple Crown winner."
How one even gets a horse ready for the Triple Crown races is a different animal than it was in the '70s.
First, there is the trend of trainers wanting to allow more time between starts in hopes of avoiding the dreaded "bounce" factor off of big efforts. However, with the 20-horse Derby field being determined in part by graded stakes earnings since 1986, some say they now have to ask more of their prospects earlier in order to secure the crucial money needed.
"It is not a three-race series anymore, it's more like a five-race series," said Hall of Fame trainer D. Wayne Lukas, winner of 13 Triple Crown races. "In the '50s or '60s, you could take a soft approach and train your horse and come May say, 'I think he's good enough' and run him in the Derby against 10 or 12 horses. Now you cannot do that.
"You've got to say, 'We better run good in the Rebel Stakes, the Arkansas Derby, the Fountain of Youth.' We better go to the well because the earnings are so imperative for us to get in."
While the race for graded earnings has played a role, it is the monetary action brought on by the auction arena that has been arguably the biggest factor in the Triple Crown drought.
Money changes everything
Where once homebreds ruled the classics, the rise of the commercial marketplace in the past 30 years has prompted breeders to produce a different type of athlete than previously demanded.
With deep-pocketed buyers like Robert Sangster, Coolmore, and Sheikh Mohammed bin Rashid al Maktoum arriving on the scene in the 1980s, wild bidding wars erupted that produced seven- and eight-figure yearlings as well as broodmare prospects.
Since buyers need to get as much return as possible on such lofty investments, precocious babies that could inspire a strong following in the breeding shed went to the top of buyers' wish lists, regardless if they had classic ability.
"There might be a tendency to try and breed a powerful speedy horse as opposed to one that looks like it could run a distance of ground. But you have to understand that commercial breeders are breeding what they think they can sell," said bloodstock adviser Ric Waldman, who managed the career of leading sire Storm Cat. "And I think the end user has wanted a speedy horse.
"It's not like we don't want to breed Derby winners, everybody wants a Derby winner. But it goes back to the type of horse we think will make a good stud horse. And the kind of horse we think will make a good stud horse has typically been one that has shown speed and precocity."
In trying to breed fast, pretty horses, some argue the durability of the modern Thoroughbred has been sacrificed along with the stamina. Today's runners might not be the iron horses of the past, but part of the issue behind their perceived fragility may be just that — perception.
"I cannot believe how well these horses handle the comeback (during the Triple Crown)," Motion said. "Animal Kingdom went into the Preakness great, he went into the Belmont great and I never could have predicted that having never done it before. I don't think we give these horses enough credit for how durable they are."
Given the way the sport has changed, some like Lukas have said the Triple Crown should change with it, both in terms of the races' distances and spacing.
If I'll Have Another ends up winning this challenge, he'll not only have racing's greatest achievement on his résumé, he'll have overcome a new set of obstacles in doing so.
"It shouldn't be easy," Waldman said. "While everyone is hoping we have a Triple Crown winner, the fact there hasn't been one in such a long period of time underscores how difficult it is. You add in the component that maybe we're changing the breed over this period of time and that compounds the difficulty in trying to achieve it."