1. The Preakness, and the Triple Crown in general, has been the scene of famous rivalries. One of the more interesting if lesser known ones involved Hill Prince and Middleground, who met in the 1950 Preakness for the fourth time in less than a month. Hill Prince had defeated Middleground in the Wood Memorial on April 22, with Middleground returning the favor in the May 6 Kentucky Derby. In the week between the Derby and Preakness, the pair met again in the Withers Stakes, with Hill Prince the winner by 1 1/2 lengths. Hill Prince would take a 3-1 lead in the rivalry with a five-length victory at Pimlico, but Middleground would turn the tables in the Belmont Stakes three weeks later. Hill Prince clinched champion three-year-old honors later in the year beating Middleground for a fourth time in the Jerome Handicap.
2. The late Woody Stephens is remembered most for training five consecutive winners of the Belmont Stakes (1982-86). He also won the Kentucky Derby twice, including the centennial edition with Cannonade (1974). Less well known is that Stephens' first Triple Crown race win was in the Preakness, way back in 1952. In the absence of Derby winner Hill Gail, the Stephens-trained Blue Man was made the 8-5 favorite and provided the future Hall of Fame conditioner with his first classic victory by a comfortable 3 1/2-length margin. It was Stephens' only Preakness win in nine attempts.
3. The Preakness has been won by three successive generations on two occasions. Polynesian (1945), Native Dancer (1953), and Kauai King (1966) were the first father-son-grandson trio to capture the middle jewel of the Triple Crown. More famously, the Preakness was also won by Bold Ruler (1957), Secretariat (1973), and Risen Star (1988). The next potential occurrence could come in the near future should a son or daughter of Exaggerator (2016) wear the Black-Eyed Susans like he and his father, Curlin (2007).
4. The last several decades have seen the occasional Kentucky Derby or Belmont Stakes winner pay more than $100 to Win. Due to various factors, the Preakness has never come close to producing a similar upset. The highest-priced winner in the history of the race was Master Derby (1975), who returned $48.80 after defeating Derby winner Foolish Pleasure. He's one of only two horses in history to win the Preakness at odds of 20-1 or higher.
5. What do the longshot Preakness winners Greek Money (1962), Bee Bee Bee (1972), and Oxbow (2013) all have in common? In winning the Preakness all three defeated that year's Kentucky Derby winner and the eventual champion three-year-old, who were different horses. Greek Money won over Decidedly (Derby) and Jaipur (champion); Bee Bee Bee beat Riva Ridge (Derby) and Key to the Mint (champion); and Oxbow prevailed over Orb (Derby) and Will Take Charge (champion).