Most American workplaces start you out with 2 weeks and then usually add a week or so after so many years of seniority. When you change jobs, how many of you ask for that same amount of vacation time at the new company? Or do you just accept that you're new and don't want to push things by asking for more at the onset? Or is it just forgotten until it's too late to ask?
I find that I take a lot of what I have in my daily business life for granted and am often surprised when I'm struck by the reality of how few benefits positions in other places in this country give people.
I cannot see how you consider that he got a bad deal.
You raise an important point. There can be a bit of that. For example, negotiating additional vacation time when you start a new job can hurt you a year later when you take that vacation and things aren't going well for the company. It can be viewed negatively by management and it might bleed into other considerations, like raises or promotions. Screwed up, I know, but it happens.
My new company is 3 weeks vacation and 5 days sick/personal for everyone. Instead I just took more money with the understanding that I could get approved for leave without pay as needed.