Charles Barkley lost around $10 000 000Being an impressive personality, Barkley shocked his fans in 2006 when he told about his losses of 10 million dollars at casinos. One year later, he managed to win back almost $700 thousand when he supported the Colts to win Super Bowl XLI. Barkley was taken to court by the Las Vegass Wynn Casino for failing to pay around $400,000. Despite such situations, he doesnt seem to slow down. He is still regularly seen in various casinos in Vegas, spending huge amounts of money.
and the other three namely: J.R. Smith, Antoine Walker, and Charles Oakley.
Probably Charles Barkley fits more on the place stated on OP than Michael Jordan.
That's only a fraction on what they are earnings from their salary and from products endorsement but still they should not divulge how much they've lost and losing it harm their reputation for future endorsement , of course talent agency will have second thought hiring gamblers for fear of accusations they they are supporting their gambling habits.