How much money does he really have at this point?  Print is dying and playboy circulation is shrinking faster than a dick in a ice bath.  Porn is free these days
This was his 
monthly income in 2009 that he needed to file for his divorce
Monthly income:
 Salary from Playboy: $116,667
 Social Security: $1,896
 Dividends and interest: $121,099
 Rental property: $17,058
 Income from HMH Productions: $15,808
 Pensions and retirement: $413
 Other miscellaneous income: $17,639
Total monthly income: $290,580
Other Assets:
 $306,548 in cash
 $36,802,558 in stocks and bonds
 $6,122,990 in a joint account with an unnamed person
 Total assets (including Playboy stock and property): $43,232,096