Howard Wilkinson was arguably the worst manager Sunderland have ever had. There are numerous contenders, but he seriously might be the worst, and as a player, he wasn't much better either. Believe it or not, Wilkinson was actually a flying winger for Brighton & Hove Albion, between 1966 and 1971, before moving on to Boston United where he won two consecutive Northern Premier League Titles, and made over 200 appearances, with a stint as player/manager included.