Let me just preface this by saying that pitchers, as a whole, are much more difficult to predict than hitters, at least as far as the rest of their career goes. Pitchers are much more susceptible to random, career altering injuries, discovering new pitches, and other unusual events; therefore, there is a much greater element of randomness.
Also, the Hall of Fame seems much more unclear on what constitutes a Hall of Fame pitcher, outside of 300 wins. The last starter elected by the Baseball Writers Association (essentially, what you think of when you think of the election process) was Nolan Ryan, back in 1999.
Before him, the last choices were Don Sutton, Phil Niekro, Steve Carlton, and Tom Seaver. You may notice two things about that group. First, every one of them has 300 wins. In fact, the Baseball Writers haven’t elected a non-300 game winner since Ferguson Jenkins (only 284 wins) back in 1991; whether this says something about the Hall’s electors or the quality of pitching in that time, I can’t say.
Second, every one of the aforementioned pitchers started their career in the 1960s. Yes, apparently, it has been over four decades since any Hall of Fame starter began his career.
This doesn’t even account for the erratic process they use to elect relievers; there is no obvious milestone, or, really, any sort of standard (if you’re looking for a good example of such oddities, look up one of Joe Posnanski’s articles comparing Hall of Famer Bruce Sutter and Dan Quisenberry).
Nevertheless, I want to cover every position for the the future of the Hall of Fame; and so, I begin with my first round of pitchers.
(Note: I used Baseball-Reference for WAR throughout the article. Fangraphs calculates pitching WAR a different way, and uses a more standard scale, but they only have numbers from 1980 on. Feel free to check it out if you’re interested, though.)
(Another note: There are a lot of pitchers. Surprising, I know. So, I broke them up by division; this article will be on the AL and NL East pitchers, with ones for the Central and West to follow.)