What time was the most painful to be a Bears fan?

Discussion in 'Chicago Bears' started by Henry Burris, Oct 13, 2013.

  1. Henry Burris

    Henry Burris
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    For me, it was the 1998 and 1999 seasons. Cade McNown was so bad, I was strictly watching the Jets most of those years. Honorary mention has to go to the end of the 2002 season, when Henry Burris was starting. I think one of his games was when Dick Jauron was asked who was standing out on the team, and he answered "the punter".
     
  2. WearyBear

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    Probably 1965 to 1982. They made the playoffs a few times but they backed into them. You know, they had to depend on one team beating another to get in and they were usually eliminated in the first round. They always had a star player or two to keep the fans coming. My wife could never understand why I would get so upset watching them.
     
  3. Adibear

    Adibear
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    the Dave WINLESS Wannstedt years still leaves a bad taste in my month
     
  4. lklrlolnlilklsox

    lklrlolnlilklsox
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    Being a child of the 90s, my entire youth was wrought with terrible teams.
     
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  5. The Benjamin

    The Benjamin
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    I agree with K-Sox. The entire decade of the 90s.
     
  6. BradMustersGhost

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    going in a different direction here, but 1986-1988 was heartbreaking for me. Playoff disappointment after playoff disappointment. I STILL haven't gotten over the fact that the Skins came into Soldier Field back-to-back years to knock the Bears out of the playoffs. We wasted a heck of a lot of talent during those 3 seasons, and THAT is why I view that period as being particularly painful. We just flat out sucked donkey nutz during the Wanny years, so it's not like were having our hopes dashed year after year. I would qualify those years as "boring and depressing", but not exactly "heatbreaking" or "painful." Semantics, I know, but that's just the way I feel.
     
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  7. JustAnotherBearsFan99

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    This ^^^^^

    We were really really bad. You'd watch the games just to see one of our star players (a Sayers, Butkus, young Walter P, and some of the others). You didn't watch to see us actually "win" anything. We were crap.
     
  8. Jimmors

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    The Rhymenoceros
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    Dick Jauron era.
     
  9. AmericanPitBull

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    90's
     
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  10. Bearsinhouston

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    I think I might have thrown up just a little bit
     

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