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He has already had second chances...
When you get that low you need to grab the boot straps and take it...
I definitely would NOT hire him no matter how nice he seems. He is a player and he will play you. He obviously prefers to get things easy instead of doing the work. For all you know he is the "smart guy" for a crime syndicate and they are looking for a sucker to bleed money out of.
I actually know a guy like this and he keeps asking me for work. I keep letting him know he should have made better choices.
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