Roy Park. Played VFL for university, melbourne and footscray, from 1912 to 1921. Also played one test match at the MCG. Legend has it that his wife, who was watching in the stands, dropped her knitting as he prepared to face his first ball, bent down to retrieve it at the moment of delivery, and thus missed his entire Test career.Some suggestions:
Darren Holmes - played in five successive wooden spoon teams (Sydney Swans 1992, 1993 & 1994) and Fitzroy (1995 & 1996) and caught a pig released onto the SCG in a 1993 match against St. Kilda.
Rene Kink - played in losing Grand Final teams for Collingwood in 1977, 1979, 1980 & 1981, crossed to Essendon in 1983 and played another GF loss that season and missed selection in the Bombers' 1984 and 1985 premiership victories. Finished his career in 1986 with a wooden spoon for St. Kilda.
Lester Kelly - 40 games played for University, 40 games lost.
Jeff Hogg - Played 186 matches for Richmond (1986-1993) and Fitzroy (1994-1996) all in bottom 4 teams, with wooden spoons for the Tigers in 1987 and 1989 and Lions in 1995 and 1996. Departed AFL football having played in 33 successive losing teams.
Derek Kickett - Played in Essendon's losing 1990 Grand Final team, was omitted from the Bombers' premiership team after playing every match in 1993, crossed to the Sydney Swans where is final game was the 1996 GF loss against North Melbourne - Kickett's first AFL team. He was also disqualified from winning the 1987 WAFL Sandover Medal playing for Claremont Tigers after a suspension that year.
Richard Lounder - Richmond's prized 1987 No. 1 draft choice, who played just four games for the Tigers in 1989 before returning to the SANFL.