Bret Saberhagen: Two-time Cy Young Award winner
Eighteen pitchers have won multiple Cy Young awards. Ten of those men are already enshrined in the Hall of Fame, three (Clayton Kershaw, Tim Lincecum and Max Scherzer) are still active, two (Roy Halladay and Johan Santana) are not yet eligible and another one (seven-time winner Roger Clemens) is languishing on the ballot due to his connections to performance-enhancing drugs. That leaves just two, Denny McLain and Bret Saberhagen, whose Cooperstown fate has been sealed.
McLain stuck around for three ballots before the five percent rule was adopted, making Saberhagen the only member of that elite fraternity who appeared on just a single Hall of Fame ballot before disappearing into the ether. His career spanned from 1984 to 2001, albeit with two full seasons and several partial ones missed due to injuries. For the first six years of his career, he looked to be Cooperstown-bound. He debuted a week before his 20th birthday, won his first AL Cy Young the next season on the strength of a 20-6, 2.87 ERA season while leading the Royals to their first world championship, and added a second Cy at age 25 in 1989, when he went 23-6 with a league-best 2.16 ERA and 9.7 WAR.
To that point, Saberhagen was 92-61 with a 3.23 ERA and 32.2 WAR, the last tied with Clayton Kershaw for the fourth-highest total through an age-25 season since 1960. Unfortunately, a variety of arm injuries prevented him from ever making 30 starts in a season again, and in fact he set a record for the most games missed on the disabled list (1,016 according to Gary Gillette of the ESPN Baseball Encyclopedia). Saberhagen finished with 167 wins and a respectable 59.2 career WAR/43.3 peak WAR/51.3 JAWS line, the last of which ranks 66th among starting pitchers. Nonetheless, he received just 1.3% of the vote in 2007.