Only five horses have won both the Derby and Classic in the course of their career, and that number dwindles to three if you consider those who turned the double the same year. Moreover, the bulk of Derby-Classic winners came three decades ago.
It’s a rare historical accomplishment because each 1 1/4-mile prize establishes a different point. The Derby is the marquee proving ground for 3-year-olds in the spring, but to win the Classic, a horse has to beat all comers of every age in the fall.
The first Derby hero to add the Classic to his resume was Ferdinand, who achieved the feat as a 4-year-old. His 1987 Breeders’ Cup produced a thrilling finish with then-reigning Derby champion Alysheba. The elder Ferdinand just lasted from the hard-charging Alysheba in a race that became an instant classic at old Hollywood Park.
A more mature Alysheba came right back the following year to land the Classic at Churchill Downs. The 1988 Breeders’ Cup also featured that season’s Derby winner – the filly Winning Colors, who ran in the Distaff (G1) instead and got nabbed by unbeaten Personal Ensign in a race for the ages.
The 1989 Classic furnished another iconic clash between Derby star Sunday Silence and his arch-rival Easy Goer. Sunday Silence’s superior agility helped him prevail again at Gulfstream Park, where he became the first current Derby winner to capture the Classic.
The very next year, 1990 Kentucky Derby conqueror Unbridled joined him by taking the Breeders’ Cup Classic at Belmont Park. But the heyday of Derby winners in the Breeders’ Cup was ending.
Although the 1991 Classic pitted Unbridled against reigning Derby winner Strike the Gold back at Churchill, it didn’t have the cachet of the 1987 Ferdinand-Alysheba match-up. Unbridled hadn’t had a very productive campaign, while Strike the Gold was winless since the Derby, and they were only the fourth and fifth choices, respectively. The race shape turned out to be against them as well. As front-running Black Tie Affair held sway at every call, Unbridled closed for third and Strike the Gold finished fifth.
Alysheba wins the Kentucky Derby (Kentucky Derby/Churchill Downs Photo)
The last time two Derby winners squared off in the Classic, the 1991 edition ushered in a negative trend regarding their chances. Nine of the next 10 times that a Derby winner ran in the Breeders’ Cup, he wound up unplaced – Strike the Gold (again as a 4-year-old in 1992), Go for Gin (1994), Fusaichi Pegasus (2000), War Emblem (2002), Funny Cide (2003 and as a 4-year-old in 2004), Giacomo (as a 4-year-old in 2006), Street Sense (2007), and Mine That Bird (2009 Classic and at 4 in the 2010 Dirt Mile).
The outstanding exception to that trend was Silver Charm. The 1997 Derby victor was freshened following his agonizing Triple Crown near-miss and thus skipped that fall’s Breeders’ Cup, but as a 4-year-old, he placed a close second to Awesome Again in the all-star 1998 Classic at Churchill.
The trend appears to be cycling back in recent years, with the past three Derby winners performing well in the Breeders’ Cup. Animal Kingdom, the 2011 Derby champ, was a flying if troubled runner-up to Wise Dan in the 2012 Mile (G1) on turf.
California Chrome was third in a tight finish in the 2014 Classic, nearly pulling off the double in his Derby year. In his next Breeders’ Cup try in 2016, “Chrome” again ran valiantly in defeat, beating all bar the late-developing sophomore Arrogate.
American Pharoah, who ended the 37-year Triple Crown drought in 2015, also ended the drought of Derby winners in the Breeders’ Cup. Just the third to complete the Derby-Classic double in the same season, after Sunday Silence and his own male-line ancestor Unbridled, “Pharoah” went out on a high note at Keeneland.
Authentic’s bid has something in common with Pharoah’s aside from the Keeneland venue. Both are trained by Hall of Famer Bob Baffert, a three-time Classic winner who also had the aforementioned Arrogate (and Silver Charm).
The obvious difference, aside from the fact he’s not a Triple Crown winner, is that Authentic won the pandemic-postponed Derby on Sept. 5. Instead of peaking in late spring, and trying to return to that peak several months later in the fall, Authentic just needs to maintain his form.
Baffert is known for getting the best from his horses through the traditional Triple Crown schedule, and Authentic’s sequence of a Derby victory, followed by a hard-fought Preakness (G1) loss, makes the Classic more akin to the third leg – albeit in deeper waters versus elders.
If Authentic can join the exclusive club of Derby-Classic winners, he’d receive a more tangible benefit as well. A $1 million bonus is offered to the 3-year-old who can sweep both races on top of the Haskell (G1), and Authentic made himself eligible by holding on in that July 18 feature at Monmouth Park. Note that American Pharoah won the Haskell in 2015 too, as did Baffert’s Bayern en route to his 2014 Classic score.
Maximum Security likewise won the 2019 Haskell, in the wake of his disqualification as the first-past-the-post in the Kentucky Derby. Last year’s champion 3-year-old male thus isn’t an official Derby winner, but the same historical perspective applies, in a certain sense, as he tackles the Breeders’ Cup Classic – now as Authentic’s stablemate in the Baffert barn.
If not for Maximum Security’s demotion at Churchill, we could say that the 2020 Classic is the first meeting of Derby winners in the Breeders’ Cup since 1991, and second overall. It’s a deep Classic field, but if Maximum Security and Authentic can fight out the finish, it would conjure up memories of Ferdinand and Alysheba in 1987.