St Kilda's 98 losses from 100 matches 1897-1903.
They were only in the League because:
1. They played at a ground (the St Kilda Cricket Ground) which was very well located regarding public transport.
2. Their players were regarded as 'very nice chaps' and 'good sports'.
3. Their rival for a place in the league, Port Melbourne were regarded as 'unsporting thugs'!
Well, GWS only won 3 of their first 44 matches (not quite as bad admittedly), but:
They were only in the League because:
1. They played in a region where no one was interested in the game at all, but the organising body (AFL) was thinking primarily about potential TV revenue.
2. There were 17 teams in the league, and adding another club meant an extra game each week, meaning more potential TV revenue.
3. Their rivals for a place in the league (Tasmania), despite having had an australian football culture lasting 160 years, producing multiple premiership captains, Brownlow medallists, Coleman Medallists and other egendary players at the highest level, were deemed to provide less potential TV revenue.