"Royalties", you mean?
As it happened they were too afraid to go up against Roy Cohn, the owner of Columbia and a man with many Mob connections, so they settled for re-negotiating their contracts every year, most of the time for raises of a few dollars.
The 3 Stooges were a complicated case. They set up the Comedy III corporation in 1958 to protect their "brand" but Columbia still owned all the rights to their TV shows and movies. The boys' families began to squabble over how to divvy up the money and it all started falling apart.
While the brothers all passed at fairly young ages, I'm not sure that I would say they were destitute - they were more than comfortable, although certainly not as wealthy as they should have been.
Earl Benjamin, the stepson of "Curly" Joe DeRita, and his brother Robert stepped in in 1999-2000, made peace among the heirs and began battling to secure the rights to all the merchandising of the 3 Stooges - coffee mugs, fake driver's licenses, posters, etc.