Of current pitchers, Sabathia is probably the only one with a reasonable, albeit remote, shot at it. He still needs over 100 wins though and he's already 32. With the way pitchers are handled these days, we might not see one ever again.
Kershaw looked like he had a shot, but seems like injuries are starting to catch up to him, so probably not. Bumgarner or Sale could maybe have a chance if they stay healthy and their teams are great for the next ten years or so. Other than that, not much in terms of candidates.
Seven years later, Sale isn't even halfway there. Bumgarner is less than halfway there and is out of the league. Sabathia is retired with 251 wins. Kershaw has 212 at age 37 and has barely pitched in two years. Verlander is the closest, at 262 wins and still active. He is 42 though, and he looks like he might be toast. I think even 275 is a reach for him at this point.
Everyone else who has been in the league a while has no shot. It will take a young arm like Skubal or Skenes to be the next person to do it, if their teams will let them pitch enough. Otherwise, Randy Johnson will be the last guy to ever do it. Wild.
I am learning baseball players with these quizzes. Only knew Babe Ruth before more or less pre-Jetpunk. Did another pitching quiz earlier tonight and now I scored 54%. That's 4/5. If I'd just one day remember its "seaver", not "sawyer" or "sayers" or "saunders" or any other name I keep wanting to call him.
As of November, 2018 Bartolo Colon is 45 and has 247 wins. He won 7 games in 2018 and appears to have no chance of breaking 300. C C Sabathia is 38, won 9 games in 2018 and has 246 wins. He has a better chance of reaching 300, but not a good one.
Would suggest referring to #3 as Grover Cleveland Alexander or Grover Cleveland "Pete" Alexander. Although Baseball Reference refers to him as "Pete," his Hall of Fame plaque reads "Grover Cleveland Alexander" and that is by far the name most frequently used in referencing him. "Grover Cleveland" was his given name and it appears that "Pete" or "Old Pete" was a nickname.
Everyone else who has been in the league a while has no shot. It will take a young arm like Skubal or Skenes to be the next person to do it, if their teams will let them pitch enough. Otherwise, Randy Johnson will be the last guy to ever do it. Wild.