The sire line of Curlin was responsible for 80-1 Kentucky Derby (G1) upsetter Rich Strike, and now the Hall of Famer goes for an encore with a couple of longshots in the 2022 Preakness (G1).

Curlin belongs to an exclusive club of Preakness heroes who have gone on to sire winners of the middle jewel. While Curlin turned the tables on Derby champ Street Sense in the 2007 Preakness, his son Exaggerator did the same versus 2016 Derby victor Nyquist in their rematch at Pimlico.
Exaggerator hopes to join the sires’ club himself, with his colt Skippylongstocking on Saturday. If Skippylongstocking can spring a 20-1 surprise, he’d become a third-generation Preakness winner. 
This grandsire-sire-son winning sequence has happened twice before in the Preakness. Polynesian, the 1945 Preakness scorer, sired Hall of Famer Native Dancer (1953) who in turn got Kauai King (1966). Hall of Famer Bold Ruler, who captured the 1957 edition, is responsible for the all-time great Secretariat (1973), himself the sire of champion Risen Star (1988).
Skippylongstocking’s dam is by War Chant, the broodmare sire of 2019 promoted Derby winner Country House. Skippylongstocking comes from the family of 1999 Derby and Preakness star Charismatic. Both descend from Grass Shack, a daughter of the aforementioned Polynesian, from the tribe labeled 10-a.
Curlin, who is himself a male-line descendant of Native Dancer via Mr. Prospector, also has a son of his own in Saturday’s renewal. Fenwick, listed at 50-1 on the morning line, is projected to be the longest shot on the board. Fenwick is bred along similar lines to Exaggerator. Both are out of Seattle Slew-line mares, in Fenwick’s case, a daughter of Malibu Moon. A son of Hall of Famer A.P. Indy, Malibu Moon is the sire of 2013 Derby hero Orb and broodmare sire of last year’s Preakness runner-up Midnight Bourbon.
Aside from the victorious Exaggerator, Curlin has sired two who placed in the Preakness – Ride on Curlin, runner-up to California Chrome in 2014, and Tenfold, a close third to Justify as a 26-1 shot in 2018. If Fenwick can somehow shock the world, Curlin would emulate his sire, Smart Strike, by siring two Preakness winners. Smart Strike’s second winner of the middle jewel was champion Lookin at Lucky (2010). 
Oxbow, who wired the 2013 Preakness, is another trying to join the sires’ club through his son, Happy Jack. The 30-1 shot is out of a mare by the patriarch Tapit, whose classic success has come as the sire of a record-tying four Belmont (G1) winners. Happy Jack’s granddam is by Alysheba, who turned the Derby/Preakness double in 1987. 
Happy Jack traces to the same maternal line, dubbed 3-o, as 1956 Preakness victor Fabius. Ironically, Fabius was also a Calumet homebred, like Happy Jack. But their connection was not nurtured on the farm. Calumet bought Happy Jack’s dam, Tapitstry, and her common ancestress with Fabius is the 19th-century British matron Black Duchess.
Secret Oath hails from the 9-f family of three Preakness winners, including fellow filly Nellie Morse (1924), but in a remote fashion going back to the Toxophilite mare (foaled 1861). Secret Oath descends from her granddaughter Astrology, dam of *Star Shoot (a leading sire who was responsible for the first Triple Crown winner, Sir Barton). The aforementioned Lookin at Lucky actually has a nearer matrilineal relationship to Nellie Morse, while last year’s hero, Rombauer, descends from another segment of the 9-f line. 
Secret Oath’s male line has been productive in the middle jewel as well. Although sire Arrogate developed too late for the classics, his paternal grandsire Unbridled won the 1990 Derby and finished second in the Preakness. Unbridled sired 2000 Preakness scorer Red Bullet, and Unbridled’s sire line has given us 2015 Triple Crown sweeper American Pharoah.
Secret Oath’s broodmare sire, Quiet American, has also been prominent in Preakness-winning pedigrees. The sire of 1998 Triple Crown near-misser Real Quiet, Quiet American is the damsire of 2006 champion Bernardini.
Because Quiet American and Unbridled are both by Fappiano, Secret Oath is inbred to that influential son of Mr. Prospector. Fappiano factors in her Preakness rivals too, especially through his male-line descendant Candy Ride, the paternal grandsire of Early Voting and broodmare sire of both Epicenter and Simplification.
Early Voting is from the banner first crop of Horse of the Year Gun Runner, by Candy Ride. If Early Voting prevails, he’d become the second straight grandson of Candy Ride to take the middle jewel. The 2021 hero, Rombauer, is by the Candy Ride stallion Twirling Candy.
Early Voting’s dam, Amour d’Ete, is a full sister to Irap, the 2017 Blue Grass (G2) winner (by Hall of Famer Tiznow) and a half-sister to successful sire Speightstown. This 9-b female line traces to the celebrated Hildene, dam of Hall of Famer Hill Prince, the 1950 Preakness hero. 
Both halves of Early Voting’s pedigree include the prolific Storm Cat. Gun Runner’s dam is by Storm Cat’s greatest son, Giant’s Causeway, while Storm Cat is himself the broodmare sire of Amour d’Ete.
The “Iron Horse” Giant’s Causeway is the paternal grandsire of three Preakness contenders. Morning-line favorite Epicenter and Simplification are by the young Giant’s Causeway stallion Not This Time; they’re also bred on the same cross, being out of Candy Ride mares.
Epicenter has a leading chance to become the fifth Preakness winner from the 21-a tribe. Buskin (1913) and Victorian (1928) (a half-brother to 1927 Derby victor Whiskery) share the same immediate family, while Deputed Testamony (1983) and Tank’s Prospect (1985) descend from the Irish import *Clonaslee (foaled 1922). Epicenter’s Anglo-Irish maternal line traces to an ancestress of *Clonaslee, Anonyma (foaled 1859).
Simplification belongs to a terrific family, with his second dam being a full sister to Hall of Famer Ashado. Yet the 16-g tribe has yet to produce a Preakness winner; one of its standouts, 1942 Derby and Belmont star Shut Out, lost the Triple Crown because he was fifth at Pimlico.
The other grandson of Giant’s Causeway, Creative Minister, is by Creative Cause, the third-placer in the 2012 Preakness. Like Happy Jack, Creative Minister is out of a Tapit mare, but his immediate family boasts more black-type. 
Creative Minister is a half-brother to five stakes performers, including 2017 Wood Memorial runner-up Battalion Runner. Their dam, Tamboz, is herself a full sister to Tapizar, the 2012 Breeders’ Cup Dirt Mile (G1) winner. A member of the 8-d family, he traces to a distant ancestress in common with the aforementioned Bold Ruler, the British mare Feronia (foaled in 1868).
Armagnac comes from the same A4 family as California Chrome, both descending from the prolific Judy-Rae (foaled in 1944). Fellow Preakness winner Kauai King counts as a member of the tribe via a more extended route, with their common ancestress being the great racemare Wanda (foaled in 1882). A much nearer maternal relative, Strodes Creek, was second in the Derby and third in the Belmont in 1994.
Armagnac’s sire and broodmare sire represent different branches of Mr. Prospector. He’s by Quality Road, a son of Elusive Quality like 2004 Derby and Preakness romper Smarty Jones. Armagnac’s dam is by Lemon Drop Kid, the 1999 Belmont champion. 
Thus “Mr. P” is the male-line ancestor of five of the Preakness entrants – Armagnac (via Gone West), Early Voting and Secret Oath (via Fappiano), and Fenwick and Skippylongstocking (via Curlin). The remaining four descend from the Northern Dancer sire line, the Giant’s Causeway grandsons Epicenter, Simplification, and Creative Minister as well as Happy Jack (via Deputy Minister/Awesome Again). 
Secretariat factors deep in the ancestry of seven runners, often as the broodmare sire of Storm Cat and A.P. Indy. The two without Secretariat are Secret Oath and Skippylongstocking.