2007 New England Patriots vs. 1985 New England Patriots
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Here's a good one: How would the 2007 New England Patriots fare against the 1985 New England Patriots that got hammered 46-10 by Chicago in the Super Bowl? I tried it out on WhatIfSports.com to find out. The 1985 Patriots consistently won. Try it out yourself. Even more bizarrely, the 2007 Patriots often beat the 1985 Bears. So the 85 Bears crushed the 85 Patriots, who beat the 07 Patriots, who beat the 85 Bears. The 2007 Patriots simply could not stop the 1985 Patriots running back duo of Craig James and Tony Collins, as both consistently gained about 100 yards or more. Tom Brady, meanwhile, was held in check by the 85 Patriots, putting up rather average numbers most of the time.
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It shows the Pats have gotten lucky 17 times in a row, right?
I think it's far more likely that it shows how perhaps there may be some flaws in the WhatIf system. I'd rather put my trust in the players on the field to determine who the best team is, not made up player rankings and stats from the 80s.
(Although I do think the simulator is pretty cool...)