The Triple Crown series is made up of the biggest three races in the country and some of the most important races in the world. It comes as no surprise, then, that many of America’s best racehorses have won one or more of the Kentucky Derby, Preakness Stakes, or Belmont Stakes. But there are also plenty of fantastic Thoroughbreds that either lost those races or never got a chance to run in them. Brush up on your horse racing history and get the rundown on some of them below, in reverse chronological order.

Flightline (YOB:2018)

Flightline did not make his career debut until a week before the Kentucky Derby Presented by Woodford Reserve during his 3-year-old season in 2021, so even though he won by 13 ¼ lengths he had no chance to make the race. Injuries delayed the start of his career, but he’s made up for lost time with five victories by a combined margin of 62 ¾ lengths, including an almost unfathomable 19 ¼-length runaway in the 2022 TVG Pacific Classic Stakes that stamped him the favorite for this year’s Longines Breeders’ Cup Classic.

Gun Runner (YOB:2013)

Gun Runner was a very good racehorse as a 3-year-old, winning two key races on the Kentucky Derby trail in 2016 before running third in the run for the roses. He emerged as an absolute force when he was a 4-year-old in 2017. He won four straight Grade 1 races from June to November with dazzling speed figures, capped by a 2 ¼-length romp in the $5,520,000 Breeders’ Cup Classic, and was a slam dunk choice for Horse of the Year. He closed his career with another dominant win in the $16,300,000 Pegasus World Cup Invitational Stakes in January 2018. He won 12 of 19 career starts and earned a remarkable $15,988,500.

Arrogate (YOB: 2013)

Eclipse Sportswire

Arrogate didn't make his career debut until April of his 3-year-old season (2016) and won his first race in June just days before the Belmont Stakes. But boy, did racing fans get a gift worth waiting for. After winning a pair of allowance races in California, Arrogate shipped across the country to win the historic Travers Stakes at Saratoga in record-setting fashion. He then upset California Chrome in the Breeders' Cup Classic, and in 2017 orchestrated two monstrous wins in the Pegasus World Cup and Dubai World Cup. 

Wise Dan (2007)

Two-time Horse of the Year Wise Dan. (Eclipse Sportswire)

Wise Dan is a Grade 1 winner on turf and dirt who retired in September 2015. He has six Eclipse Awards (horse racing’s year-end championships) to his credit, including two Horse of the Year titles, and boasts a career record of 23 wins and two second-place finishes from 31 starts, with more than $7.5 million in lifetime earnings. He didn’t make his career debut until February of his 3-year-old year and didn’t run in a stakes race until October of that year, long after the Triple Crown. He subsequently became primarily a turf miler. Wise Dan seemed to get better with age, earning 15 wins and two seconds from 17 starts in 2012, 2013, and 2014. He also won the Breeders’ Cup Mile twice.

Zenyatta (2004)

Zenyatta is the only female racehorse to win the Breeders’ Cup Classic (2009), and she also won the Breeders’ Cup Ladies’ Classic (2008). She retired with 19 wins from 20 starts, with the only blemish on her record a close runner-up finish in her final career start, the 2010 Breeders’ Cup Classic. Zenyatta was named Horse of the Year that year, one of four Eclipse Awards she earned in addition to more than $7.3 million in purses over her career. She didn’t make her first start until the end of her 3-year-old season, thus eliminating any chance of running in the Triple Crown races.

Tiznow (1997)

Tiznow is best known for his two Breeders’ Cup Classic wins in 2000 and 2001, which showcased his tenacious will to win. In both races, he appeared beaten in late stretch but fought on to win what was then the richest race on the North American racing calendar. He is the only horse to win that race twice and has three Eclipse Awards to his credit, including 2000 Horse of the Year. Tiznow’s career earnings total $6,427,830, but he didn’t make his first stakes start until July of his 3-year-old year, after the Triple Crown.

Skip Away (1993)

Skip Away finished second in both the Preakness and the Belmont but his greatest moments were yet to come. He was named champion 3-year-old male in 1996, despite not winning a Triple Crown race, and champion older male in 1997 and 1998. He finally got his Horse of the Year title in 1998 as a 5-year-old. Skip Away won such historic races as the Jockey Club Gold Cup, Donn Handicap, and Woodward Stakes as well as the 1997 Breeders’ Cup Classic. His career earnings totaled $9,616,360, good for fourth all-time in the U.S. at the time of his retirement.

Holy Bull (1991)

Holy Bull won 13 of his 16 career starts but finished an inexplicable 12^th in the 1994 Kentucky Derby as a heavy favorite. That was the only Triple Crown race he competed in. Holy Bull rebounded to defeat older horses in the Metropolitan Handicap later that month, one of his six Grade 1 (highest level) wins in his career. He was named champion 3-year-old and Horse of the Year for 1994 and retired with career earnings of nearly $2.5-million.

Cigar (1990)

Cigar put together an awe-inspiring 16-race win streak beginning in October 1994, winning top-tier races in New York, Florida, Arkansas, Maryland, Massachusetts, Illinois, California, and even Dubai, triumphing in the inaugural Dubai World Cup in 1996. He won the 1995 Breeders’ Cup Classic and four Eclipse Awards, including two Horse of the Year titles, and amassed career earnings just shy of $10 million. He didn’t compete in any of the Triple Crown races as he didn’t make a stakes start until September of his 3-year-old season.

Personal Ensign (1984)

Personal Ensign won all of her 13 races, including a breathtaking victory in the 1988 Breeders’ Cup Distaff over that year’s Kentucky Derby victress Winning Colors on a muddy track she didn’t like. She won the Grade 1 Frizette Stakes as a 2-year-old but wouldn’t run again until September of her 3-year-old season, missing all of the Triple Crown races. Personal Ensign defeated males in the 1988 Whitney Handicap en route to being named champion older female that year.

Lady’s Secret (1982)

This Oklahoma-bred wasn’t burdened with high expectations early in her career, but Lady's Secret proved appearances can be deceiving. The daughter of Secretariat won 25 of 45 races and finished second or third another 12 times. She won the Breeders’ Cup Distaff, Beldame Stakes, Santa Margarita Invitational Handicap, and a slew of other races, including the Whitney Handicap against males. She earned more than $3 million in her career and took home Horse of the Year and champion older female honors in 1986, but Lady’s Secret did not contest the 1985 Triple Crown races.

Alydar (1975)

Alydar came up just short in 1978 Belmont Stakes.(NYRA Photo/Blood-Horse)

Alydar is probably the most famous Triple Crown non-winner, finishing second in all three Triple Crown races in 1978 in one of racing’s great rivalries. Alydar may have swept the series if he was born in any other year, but he had the misfortune of entering the world just a few weeks after Affirmed and later chasing him to the finish in the 1978 Kentucky Derby, Preakness, and Belmont Stakes. Alydar won six Grade 1 races in his career and is enshrined in the Hall of Fame, but an unforgettable rivalry ensures that Alydar’s name is nearly as synonymous with the Triple Crown series as Affirmed.

John Henry (1975)

John Henry was an iron horse, running 83 times in an eight-year career. He tallied 39 wins, 15 seconds and nine thirds on the turf and on the dirt, but he didn’t run in a graded stakes race until after his Triple Crown opportunity was lost. John Henry won major races like the Santa Anita Handicap, Jockey Club Gold Cup, and Hollywood Turf Cup. He won two editions of the Arlington Million and his win in the inaugural edition is immortalized in a larger-than-life statue at Arlington Park. Overall, the Hall of Famer earned $6,591,860.

Forego (1970)

Forego earned eight Eclipse Awards, including three Horse of the Year titles, in a career that spanned six years and 57 races. Finishing first, second or third in 50 of those races led to the gelding amassing nearly $2 million in earnings. He won four straight Woodward Stakes, a record that may never be matched, as well as multiple editions of the Metropolitan and Widener Handicaps in a historic career. The 1973 Kentucky Derby was the only Triple Crown race Forego ran in, finishing fourth behind Secretariat.

Dr. Fager (1964)

Dr. Fager had the rare kind of talent and versatility that enabled him to be named a champion on dirt and turf over sprint and route distances. He was a five-time champion, including a remarkable four championships he earned in 1968 when he was named champion sprinter, older male, turf male, and Horse of the Year. Dr. Fager won 18 of his 22 starts and finished worse than third just once, earning just more than $1 million. He did not compete in any of the Triple Crown races despite being a multiple stakes winner by that time in his career.

Buckpasser (1963)

Buckpasser was named champion at age 2, 3, and 4 while winning 25 races in his 31-race career. His 1966 Horse of the Year title capped a year in which he won the Travers, Woodward and Jockey Club Gold Cup but didn’t run in the Triple Crown races because of an infection in his right front hoof. His career earnings topped $1.4 million, the equivalent of more than $10 million dollars today.

Kelso (1957)

Kelso was named Horse of the Year for five consecutive years, a record unlikely to ever be matched, let alone bettered. The New York stalwart won 39 races and nearly $2 million ($14.38 million in 2016 dollars) in his eight-year career, but he did not run in the Triple Crown. Blood-Horse  ranked him as the fourth-greatest racehorse of the 20^th century, just behind Man o’ War and a pair of Triple Crown winners.

Coaltown (1945)

Coaltown in 1949 Widener Handicap. (Turf Pix/Blood-Horse)

Coaltown was a three-time champion in his four-year career, sweeping the titles for Horse of the Year and older male in 1949 and assuming the role of Calumet Farm’s star runner a year after the farm’s Citation won the Triple Crown. Citation and Coaltown were the same age, and after Coaltown finished second to Citation in the Kentucky Derby, the farm did not send him to compete in the final two legs of the Triple Crown. In 1949, Coaltown won 12 of 15 starts, with three runner-up finishes, to take home the Horse of the Year hardware.

Seabiscuit (1933)

Seabiscuit’s story has been immortalized in both a bestselling book and an Oscar-nominated movie, and his reputation has since increased. But what the 1938 Horse of the Year accomplished on the track was enough to warrant his fame. Not only did he defeat Triple Crown winner War Admiral in a Pimlico match race, he won a slew of important handicap races under high imposts (heavy weight assignments), including the Santa Anita Handicap, Massachusetts Handicap, and Brooklyn Handicap. Seabiscuit was a West Coast-based horse and didn’t find his best stride until after his 3-year-old season, so he didn’t run the Triple Crown.

This feature was originally published in 2016 and has been updated.