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I’m going to skip Darren Oliver.
Darren had a 20 year MLB career. He spent a number of years as a starter and a number as a reliever.
As a starter, he had a 82-77 record and a 5.13 ERA in 229 starts. As a reliever he was a setup guy and/or a LOOGY. He had a 3.19 ERA, 7 saves, 36-21 record in 537 relief appearances.
He played for 9 teams, including the Blue Jays for the last 2 years of his career. As a Jay he had a 2.90 ERA in 112 games, 105.2 innings.
You can’t play 20 seasons and be a bad player, but Oliver is far short of a Hall of Famer.
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It is Roy Oswalt’s first time on the ballot.
He had a better career than I thought. 13 seasons, a 163-102 record and 3.36 ERA in 365 games, 341 starts. His bWAR was 50.1.
Oswalt went 14-3 with a 2.73 ERA in 28 games, 20 starts in his rookie season, coming in second in Rookie of the Year voting, 5th in Cy Young voting and 22nd in MVP voting. The next year he was 19-9 with a 3.01 ERA, finishing 4th in CY and 23rd in MVP voting.
He won 20 games in both his fourth and fifth seasons and finished 3rd and 4th is Cy Young voting. The next year he led the NL in ERA at 2.98 with a 15-8 record.
Oswalt’s first 8 seasons were very very good. He had a 129-64 record and a 3.13 ERA in 253 games 241 starts through his age 30 season. Had he continued playing near the same level in his 30s, he’d be an easy Hall of Famer. But, from age 31 on, he had a 34-38 record with a 3.96 ERA in 112 games, 100 starts.
His teams made it to the playoffs 4 times, and he pitched well, going 5-2 with a 3.73 ERA in 13 games, 11 starts. He was NLCS MVP in 2006. He also has an Olympic Gold Medal.
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Most similar careers: None really, he’s sort of a donut hole in the transition between pre-closer era fireman and shorter career starters. We see this in that the most comparable Hall of Famers are Sandy Koufax, Goose Gossage and Rollie Fingers (all BBWAA). Andy Messersmith and Ron Guidry are the closest dots to Oswalt’s; in terms of similar value combinations you get the likes of Harry Brecheen and Jimmy Key