05_never_again
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You can make outstanding arguments for all 3.Depends on how far back you go. The Lions have one ****ing playoff win since 1957. This century, I would say the Browns. Them and the Bengals at least have the 80’s
Maybe not the most popular choice, but I actually would go Bengals. They have 6 playoff appearances and 3 division titles since 2009, but lost each of those playoff games, sometimes in absolutely heartbreaking fashion. The 5 consecutive playoff losses in a row from 2011 to 2015 would absolutely make me pull my hair out as a fan; that's even more frustrating than your team just sucking for 5 straight years and never sniffing the playoffs, IMO.
The Bengals actually have a longer playoff win drought than both the Browns or the Lions do, and there have been many seasons where they teased you and made you think they might do something. Personally, I think it is more painful as a fan to think you're going to get something and not get it rather than never think you're going to get it at all.