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Character Questions: When are the headaches too much?

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Thursday saw the news break that Chris Henry had gotten in trouble with the long arm of the law once again.  That was followed by the not so surprising news that he was released by the Cincinnati Bengals who clearly were fed up with his act.  Even less surprising (and this is not meant as a dig at NorCalDevilASU), somebody threw up a diary about the idea of signing Henry in part because of his tremendous upside.  I definitely am in no place to criticize a suggestion of signing Henry considering I was fully behind signing this guy and even more so this guy (a search for whom led me to this "classy" website).

Anyways, I would imagine this strike will not go over well with Roger Goodell and if Henry was not suspended for the season (pending appeal as always), I'd be more than a little bit surprised.  I'm not opening this up as a thread to discuss signing Henry.  Rather, I wanted to open up the discussion on the character issue as far as signing free agents and drafting certain players.  As far as I can tell, virtually every team has signed and/or drafted a guy that had red flags based on some character issue.  This brings up a couple of questions.  I'm curious what everybody's opinion is on bringing in players with red flags.  

They always say you hate a guy until he's on your team (TO, I'm looking at you).  However, before even addressing the idea of acquiring players with character issues, we have to figure out what we consider to be a character issue.  I mean they took Tarell Brown who slipped because of misdemeanor gun and drug charges.  I look at his past problems as wrong place, wrong time and he probably isn't such a bad kid.  Of course I'm also looking at this in red and gold tinted glasses.  The current brain trust rolled the dice on Antonio Bryant and after that didn't work out, you'd like to think they're skittish about bringing in a guy who will cause problems.

Of course Tarell Brown's off-the-field issues do not come close to comparing to those of Chris Henry so I guess we have to factor in the proverbial totality of the circumstances before making a decision.  Personally, I have no problem with giving guys a second chance, particularly when it will likely come cheap.  Of course, I can also acknowledge there is considerable hypocrisy in my view.  If Lawrence Phillips or Antonio Bryant had signed somewhere else, I would have probably been out there with a few sarcastic comments about signing "criminals."  They come to the 49ers though and they're not all bad; they're misunderstood; they'll be surrounded by the right kind of people and won't get in trouble.  Then you also have to consider the talent factor.  A guy who's had some brushes with the law and is supremely talented, like Chris Henry or Lawrence Phillips or Antonio Bryant, is going to get more second chances than some practice squad guy.

I think part of the hypocrisy comes from being a fan of the team, which I think is a fairly obvious observation.  I grew up in Las Vegas in the 80s when UNLV was the baddest team on the planet and everybody considered them cheaters.  As far as I was concerned the NCAA and the rest of the country could kiss off because they were just jealous.  Of course I still think that but that's another matter for another day.  

So I guess the question is what are your thoughts on character issues.  Chris Henry seems to be the threshold guy as far as clearly being out of control and not worth the headaches (or maybe not).  Is there a definitively line on who you'd accept the 49ers (or any of your other favorite teams) signing or is it a pretty tough line to mark?