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.
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.