Exactly how did Mr. Leno get so wealthy? All I know is he retired from the Tonight Show, started his own show. I sure don't hear about Letterman's car collection, or Bob Barkers collections.
In addition to being the host of the Tonight Show, Leno has never stopped doing standup, and is a workaholic. Even while hosting the TS, he would regularly work clubs, and do corporate gigs. Still does.
I'm not into his type of comedy, but he's put in the work, and comedians can do quite well, even when they don't act or do other forms of entertainment. His comedian buddies who have appeared on his show have shown glimpses of their stuff, and Seinfeld is well known for his Porsche fetish. His producer is buds with Leno and also has a car fetish. Letterman has had a small collection since during his late night host gig, but has kept it under wraps. Publicly, he's dabbled in hot-rodded Volvos with Paul Newman, and is partner in the RLL racing team.
Unfortunately for Leno, his
Garage show was just cancelled, which is probabably more painful than the collarbone, but maybe he'll shop it to another network, like MT.
He's a genuine car guy, who likes and appreciates everything, so respect for him in that respect. Not like one of the nouveau riche who buy a bunch of the latest Ferraris or whatever, pays someone to mod them (often gaudily), and thnk that money can buy cred.
So in both respects, he hasn't faked it.