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I think you have to start the list by looking at the teams that never won a ring. One possible exception would be Tampa, while having won a ring has been mostly a terrible team most of it's existence. I guess the Jets are similar as well.
Also, like most of these lists, I am putting far more weight on the Super Bowl era; what happened before then is of little interest to me.
1. The Browns. Not only have the rarely been good since the 1960's, they have usually been among the very worst teams most seasons - just terrible. Other than for the Marty era in the 80's and the Belichick regime, the Browns have been just awful, including their entire time since returning in 1999. They have been atrocious. I mean, I believe our worst season since 1970 has been a 6-10 record; the Browns would welcome that record for much of their modern era. They are the definition of a hot mess. Look at 3 key indicators to illustrate just how bad they have been: their draft picks, their # of starting QBs and their # of coaches. Look how many terrible first round picks they made.
http://www.pro-football-reference.com/teams/cle/draft.htm
2. The Bengals. Yes, have fielded better teams lately, but still can't win a playoff game. Yes, have been in two Super Bowls unlike the Browns. Yes, the Ken Anderson and Boomer eras fielded some good teams, but by-in-large, they are still losers and have posted many, many 3-13 type of seasons, Dick LeBeau posted a sweet 2-14 season as head coach.
3. The Bucs. Other than a good defense in the late 70's (lost to the Rams in NFC Championship game the year we beat the Rams in the Super Bowl) and the crew that won a ring with Jon Gruden, they have mostly been bad....very, very bad. Their team winning % is .385%. That's pretty bad, Even when they have good QB talent, which has been rare, they squander the talent (Steve Young,
4. The Jets. Yea they won a ring 100 years ago, but have been mostly a terrible team since. A few good seasons with the "NY Sack exchange." (Gastineau, Klecko and co), some decent years with Parcells and some with Rex Ryan, but for most of my life, the Jets have been awful. Other than Nameth, their QBs have been horrid. Richard Todd, Ken O'Brien, The Dirty Sanchez, Chad Pennington, Vinny Testaverde, Geno Smith, Browning Nagle?
5. The Cards. Yea, had a few decent season, here and there, including last year and in 2008 when we played them in the Super Bowl, but, most seasons, they are just bad. I remember when Neil Lomax had the offense humming in the 80's, and they had a short run with Kurt Warner but they haven't had much luck other than that. But Uncle Brucie has them on the rise.
Honorable mention bad teams: Jags, Bills, Chiefs, Lions.
Also, like most of these lists, I am putting far more weight on the Super Bowl era; what happened before then is of little interest to me.
1. The Browns. Not only have the rarely been good since the 1960's, they have usually been among the very worst teams most seasons - just terrible. Other than for the Marty era in the 80's and the Belichick regime, the Browns have been just awful, including their entire time since returning in 1999. They have been atrocious. I mean, I believe our worst season since 1970 has been a 6-10 record; the Browns would welcome that record for much of their modern era. They are the definition of a hot mess. Look at 3 key indicators to illustrate just how bad they have been: their draft picks, their # of starting QBs and their # of coaches. Look how many terrible first round picks they made.
http://www.pro-football-reference.com/teams/cle/draft.htm
2. The Bengals. Yes, have fielded better teams lately, but still can't win a playoff game. Yes, have been in two Super Bowls unlike the Browns. Yes, the Ken Anderson and Boomer eras fielded some good teams, but by-in-large, they are still losers and have posted many, many 3-13 type of seasons, Dick LeBeau posted a sweet 2-14 season as head coach.
3. The Bucs. Other than a good defense in the late 70's (lost to the Rams in NFC Championship game the year we beat the Rams in the Super Bowl) and the crew that won a ring with Jon Gruden, they have mostly been bad....very, very bad. Their team winning % is .385%. That's pretty bad, Even when they have good QB talent, which has been rare, they squander the talent (Steve Young,
4. The Jets. Yea they won a ring 100 years ago, but have been mostly a terrible team since. A few good seasons with the "NY Sack exchange." (Gastineau, Klecko and co), some decent years with Parcells and some with Rex Ryan, but for most of my life, the Jets have been awful. Other than Nameth, their QBs have been horrid. Richard Todd, Ken O'Brien, The Dirty Sanchez, Chad Pennington, Vinny Testaverde, Geno Smith, Browning Nagle?
5. The Cards. Yea, had a few decent season, here and there, including last year and in 2008 when we played them in the Super Bowl, but, most seasons, they are just bad. I remember when Neil Lomax had the offense humming in the 80's, and they had a short run with Kurt Warner but they haven't had much luck other than that. But Uncle Brucie has them on the rise.
Honorable mention bad teams: Jags, Bills, Chiefs, Lions.