Happens more often than we know! I think the players even had to help out Borg who just had some awful luck in business! He should be sitting pretty, but the biggest fall IMO is Becker! He owned Germany but ended up needing that job as coach of Nole! I seem to remember besides the controversial personal life, businesswise he must have really screwed up! So many wanted to be in the aura of this kid way back when! Some who are more conspiratorial might think Tiriac took more than his share; hence him being the 1st tennis billionaire!
I don't know that lot of players helped out Borg financially - just McEnroe. A lot of them from that era were hurting financially themselves. Only a few guys really made a decent amount of money and have fairly well-off lives these days. The thing with Borg wasn't just that he had bad business dealings, but because he retired at 25 he just didn't have that extra 4-6 years of income at the top level that most players had. And non-tennis endorsement deals weren't really that big a deal in his heyday. That probably started around 1980-81 as McEnroe ascended to the throne. Of course it went to a whole other level with Agassi, but because he retired so early Borg missed out on all of that stuff. And also, he split with his long-time girlfriend around the time he retired and I seem to remember there was a payout involved in that split that was a significant chunk of his money.