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2. Von Joshua - 1977: -2.4 WAR
Von Joshua's claim to fame as a baseball player was his 1975 season with the Giants where he slashed .318/.359/.448. A lack of power limited him to just 2.2 rWAR that season, but it was still a fine year and likely helped convince Milwaukee to bring him into the fold during the 1976 season.
However, things went sideways for Joshua in 1977 in a big way. Joshua's .261/.286/.384 was pretty rough especially given his complete unwillingness to draw a walk. When combined with some less than flattering defensive numbers out in center field and you have the second worst season by a Brewers position player by WAR of all time.
1. Ted Simmons - 1984: -2.6 WAR
It is pretty hard to actually play enough to accumulate -2.6 rWAR, but Ted Simmons pulled it off in 1984 to claim the top spot. Simmons 21 year career in baseball was largely excellent. He made nine All-Star teams from 1971 to 1983 while averaging an .815 OPS with the Cardinals and Milwaukee. There wasn't much cause to think that Simmons was about to decline has hit .308 with 13 homers in 153 games during the 1983 season.
However, the 1984 season was the worst season of Simmons career by a mile as he slashed .221/.269/.300 with just four homers and some seriously declining defense. Simmons would rebound and put up three more productive seasons before Father Time finally caught up with him. He retired in 1988 and has since spent time as a front office executive and scout ever since. Overall, an outstanding career in baseball but one with the unfortunate blemish of putting up the worst season by WAR in Brewers history.