95. Sam Crawford

This hall-of-famer—and an absolutely legitimate one at that—began his career with the Reds for four short years, and showed tremendous promise (leading the league with 16 HR and posting a 167 OPS+ as a 21 year old in 1901) as a nascent superstar. After the 1902 season, bidding wars popped up all over the league as NL and AL teams begun fighting for player services. Crawford signed contracts with both the Reds and Tigers, and a judge awarded his talents to the Tigers, where he played 15 more seasons, eventually becoming the all-time leader in triples (still standing).

94. Chuck Dressen

Dressen had an abrupt and exaggerated career path, in which he didn't break into the majors until age 26, became a decent player at age 27, posted a peak season at age 28, and was washed up by age 30. His peak season saw him finish 3rd in the NL in doubles, 9th in triples, and 5th in walks, to accompany typically above-average defense. After retiring as a player in 1933, he was hired late in 1934 to manage the Reds, which he did for portions of four seasons, never posting a winning record in any of them. Much later, he skippered two pennant winners for Brooklyn in the 1950’s.

93. Ivey Wingo

One of the executive decisions made in putting together this list was to give "extra credit" for outstanding post-season performance, where applicable. Wingo’s work in the 1919 World Series boosted him 4-5 slots on this list, despite appearing in only 3 out of the 8 games in the Series that year. As part of an inextricable platoon with Bill Rariden that year (Wingo 1919 OPS+: 114, Rariden: 70), Wingo made the most of his World Series playing time, reaching base 7 of the 10 times he came to bat. When Wingo retired in 1929, he held the NL record for most games played at catcher.

92. Wally Post

I had remembered reading about Post as a 1950’s era slugger, and was surprised to see his numbers to be so unspectacular. His peak season was pretty good: .309 average, 40 HR, 109 RBI, 143 OPS+, but he never again approached anything like that. In the pennant-winning season of 1961, he combined with Jerry Lynch to form a very strong platoon in left field, and was one of the few bright spots in the doomed series. What I find fascinating with Post are the Reds’ transactions related to him: after a very bad 1957 season, the Reds sent Post to the Phillies for Harvey Haddix; Post played well for the Phils for 2.5 seasons, then came back to the Reds in 1960. Haddix also pitched quite well in his one season for Cincy, but after that year was packaged with Smoky Burgess and Don Hoak for four players who played a combined 216 games for the Reds—all with poor results. Meanwhile, Haddix went on to pitch one of the most famous games in history, Burgess turned into a perennial all-star behind the plate, and Hoak put together a couple strong seasons, including one where he was the NL MVP runner-up.

91. Rube Bressler

One of only five players since 1900 to appear in at least 50 games as a pitcher, and 50 games as a non-pitcher (a list that includes Babe Ruth and Joe Wood), Bressler was uniquely talented, though at the end of the 1920 season, one might have projected an early end to Bressler’s career, given his frequent injured status and his subpar hitting stats. In 1921, however, Bressler committed to a full-time position player role, and gradually improved his hitting to the point that over the three-year period from 1924-1926, he was a consistent .350 hitter, with consecutive OPS+ marks of 133, 131, and 147.