Ricky Martin may not be "big" on the mainstream USA market, but he still does well with the Latin market. Hey, the man owned then sold a nice sized place in the Time Warner complex on Central Park South, then moved on to Tribeca/Financial centre, not to mention his other properties in Miami and elsewhere. Adding to this the funds to engage a surrogate to birth his two sons (and keep quiet about it), and so forth. So would say his money has to come from somewhere.
As for "gambling", most of these bets started either in college or when one was working in various offices. You know, it would be a slow day and us girls sitting around reading magazines and gabbing, sooner or later someone would gush about how so and so was so "handsome" and wanted to marry whomever that man was. Of course they never would believe said man was "not the marrying kind", so would offer to make a wager. The rest, as they say is history.
So far have called and collected on:
Lance Bass ,(back when he was still with Insk, or whatever that band was called).
Neal Patrick Harris
Sam Champion (local weatherman)
Anderson Cooper
Mike Woods (another local weatherman)
Jim McGreevy (disgraced former governor of New Jersey)
Edward Koch (former mayor of New York City)
To name a few.
Now if Tom Cruise, Calvin Klien and a few more pan out, just maybe able to purchase that retirement condo on Boca! *LOL*