Because lending money is always about trust and managing risk.

In the context of potentially offering to float cash to a stranger - and getting a vague response about the exact situation requiring urgent cash - I'd like to know whether the person is trustworthy. Finding a mug shot that potentially resembles the cartoon version of the person requesting the cash from their website ( [link redacted] ) I see no harm in asking whether the person in the mug shot with the same name and potentially similar physical attributes was the same person.

Except that he never asked anyone to lend him money. He asked for someone to hire him on a contract basis.

Totally accurate. But he also replied to my question about why he needed the money in the context of the money being a loan rather than for work performed, so I continued the discussion.

Personally, I'd trust somebody with $300 before I'd trust them with my codebase.

I feel that asking in private may have been understandable, but posting it publicly was over the line.

Let's say you're applying for an incredibly basic credit card with a line of $1000. Would you expect the bank to obtain a copy of your credit report? Probably; that's standard practice. Would they also try to determine prior convictions? Maybe. Would you expect them to search for a mugshot of you based on a cartoon they saw, pick a totally unrelated image file, then factor what that person looks like and what they've been accused of pre-trial into the decision? I hope not.

If you're planning to spot a fellow HN user some money, and you can't show them any trust, at least show a little professionalism. If you just did that for your own amusement, please don't ever do it again.

I didn't search for a mugshot. I searched for his name, and it was the first photograph shown on the first page of the results.

Your suggestion that this was done for amusement is incorrect. A basic name search for a person in "urgent" need of money from strangers where no friend or family is able or willing to help seems like pretty basic due diligence to me.

Additionally - I'd refuse to ever lend to anybody that was an active gambler:

"@[name redacted] Hello, do you honor bets where you have made an error with the odds? (Sports book not exchange)"

[link redacted]

The exact nature of my original question was trying to determine what the money was for, and that question remains unanswered.

Your matching algorithm is about as accurate as a name match for a TSA no-fly list. Regarding the cartoon likeness, the only similarity I saw was the hairline... ok, that and two eyes, two ears, a nose, a mouth. To be honest, the cartoon image looks more like Ben Affleck.