Of course you might likely continue if the riches give you time to spend the money as you want. When you are rich you only begin to exhibit some of the character traits that poverty or being broke didn't permit you to do. Eventually when you are rich the money is there to gamble.
Becoming rich doesn't make a person to stop looking for more money. Because they are insatiable, humans always want more. As you said, wealth has the wonderful quality of enabling you to do anything you want, including investing in the things you want. No one has ever made enough money to stop thinking about how to make more, and the same is true of riches obtained through gambling.
It is in the nature of all gamblers to forget about the dangers of gambling once they have won, and even if a gambler does acknowledge the risk, their only motivation is to be lucky and thus make more money. With this mindset, it will be impossible for a gambler who has won before to stop gambling.