I was going to skip Tim Wakefield, but he had a pretty decent career.
He played 19 seasons in the MLB, had a 200-180 record (and 22 saves), 4.41 ERA. Pitched in 627 games, 463 starts. His bWAR was 34.5.
Wakefield only played in 1 All-Star game, got Cy Young votes once (coming in 3rd in 1995). He also got MVP votes that year (13th in the voting).
19 seasons, and he just played for just 2 teams, 2 seasons for the Pirates, then 17 for the Red Sox.
He pitched in 18 playoff games, starting 11, but didn't have much luck, 5-7 with a 6.75 ERA. And, of course, he was the loser in game 7 of the 2003 ALCS, the game that is mostly remembered for Grady Little's stupidity in leaving an obviously tired Pedro Martinez in the game long after he should have been pulled. Martinez would give up 3 runs in the 8th inning, changing a 5-2 lead into a 5-5 tie. Despite that, Wakefield has 2 World Series wins.
I remember Wakefield's rookie season, 1992, with the Pirates. He came up in July, made 13 starts, and went 8-1 with a 2.15 ERA, helping the Pirates make the playoffs.
In the playoff series against the Braves, Tim started game 3, with the Pirates down 2-0 and got the win. Reporters asked Pirates manager Jim Leyland if they would have Wakefield come back and pitch game 4 (two days later), since, being a knuckleball pitcher, he could really throw everyday (and he was clearly their best pitcher at the time).
Leyland said something like 'I respect the integrity of the game too much to do that'.
I hated that....If I owned the team, I would have fired him before he finished the sentence. I couldn't understand why a manager would have concerns other than winning. I mean, it might have been thinking outside the box (especially back in 1992), but it seemed obvious, you best pitcher could really throw every day, why not use him?
Wakefield would start and win game 6, (he threw two complete game wins in the series) but the Pirates lost game 7.
It turned out ok for Wakefield, he would win two World Series rings with the Red Sox, but the Pirates haven't been to a World Series since 1979.
Wakefield had a short stint as closer for the Red Sox, in 1999.
For me he is short of the Hall, but not all that much short. 220 wins is going to be a pretty high number in the current baseball era. Roy Halladay had 203 wins.
A lot of debate about the Hall of Fame relates to comparing a candidate against others elected and excluded. The chart below shows pitchers who played the majority of their career after 1945 (excluding active players, and those on the ballot or yet to hit the ballot) according to how long they played (innings pitched) and how productive they were (adjusted ERA). This is not meant to be definitive, but a high level starting point showing how players with similarly productive and lasting careers have fared.
Similar Players: Catfish Hunter (BBWAA), Vida Blue, David Wells, Kenny Rogers, Jim Perry, Bob Welch, Danny Darwin, Claude Osteen, Fernando Valenzuela, Bartolo Colon (active).