About 3 years ago, my coworker "Charles" convinced 14 people in my org to join a Fantasy Football league with a $100 buy-in. (14 people pay $100 at the beginning, and then the $1,400 would be distributed to the top 3 teams). I was not one of these people. It was a bit much for an office pool, but he convinced everybody that it would be fun since everybody liked football.
2 days after he collected everybody's money, Charles quit the company. Our company had a stupid policy of escorting people out of the building the moment they gave notice of leaving, so nobody got the traditional 2-week notice that he was leaving.
When Charles quit, nobody had his contact information. (No e-mail, cell, address, linkedin, twitter, etc.) He also hadn't yet created the Fantasy Football league. So basically, he had taken everybody's money, but nobody had any way of contacting him. People were furious. A few e-mails were sent to HR asking for his contact info, but HR said it was against policy to give out this information. I secretly found this whole situation hilarious, but kept my mouth shut.
Fast-forward to today: I'm working at a completely different company and we're interviewing a new team member. Lo and behold, Charles shows up at the interview. He does great, and everybody wants to hire him. I really like Charles, too, and would enjoy working with him again. (He's a hard worker, one of the best developers I've ever met, and always pulls hilarious practical jokes on people).
My boss asked me what it was like working with Charles. Is it wrong for me to purposely avoid bringing up this whole Fantasy Football fiasco? I fear that it might come back to me in some way if I don't say anything, but I really don't want to bring it up and sink Charles' chance to join our team. Is it wrong for me to give him the benefit of the doubt and just assume this was an unfortunate mix-up?