Right now Oakland is worse. Detroit just made the first move towards improvement by firing Matt Millen. Whoever replaces him can't do much worse, and perhaps the Lions' ownership has learned something from that mistake. In my opinion the Raiders are not going to get better until Al Davis relinquishes control, and it looks like that is not going to happen until he dies. Al Davis the owner needs to fire Al Davis the GM, Al Davis the Director of College Scouting, Al Davis the Director of Pro Scouting, and Al Davis the Director of Player Personnel.
Now if the question is which is the worse franchise over the entire history of these two teams, then the answer is obviously the Lions. The Raiders have a history of success, as recent as six years ago; the Lions have one playoff win in the last half-century. The Raiders have 3 titles, 5 conference championships, 21 playoff appearances, a 25-18 playoff record, and an all-time record of 401-316-11 (.559). In 48 years the Raiders have 26 winning seasons and 15 losing season. The Lions have 4 titles, 14 playoff appearances, a 7-10 playoff record (1-9 since 1957), and an all-time record of 488-556-32 (.468). In 78 years the Lions have 33 winning season (9 were before 1940) and 39 losing seasons (7 in a row and 22 since 1970).