How old are those debts?
"On February 5, 1997, a civil jury in Santa Monica, California, unanimously found Simpson liable for the wrongful death of and battery against Goldman, and battery against Brown. (The Brown family had not filed a wrongful death claim.)[112] Simpson was ordered to pay $33,500,000 in damages: $8.5 million in compensatory damages to the Goldman family, and $12.5 million in punitive damages to each family.[113] His net worth at the time was $11 million"
Why arent they already paid?
He claimed he didn't have the money and took actions to reduce his liability / tried to hide income so it wouldn't be directed toward this debt.
Im assuming theres a reason the court disnt put him back in jail for not paying it?
This is was a civil trial, he was acquitted on the criminal charges. His income was garnished and directed toward this debt.
If they were contesting this for years then why would that not resolve?
The families did keep taking him to court. An example is If I Did It the book he tried to publish and the families took control of the publishing and proceeds, shrinking the "If" so it looks like the title of the book is "I Did It."
This is a case of the rich/celebrity playing the system in a way normal folk can't; though in this case the families of the victims kept the pressure up so he needed to watch his step and got financial slap downs when he missteped or was caught trying to keep money without paying them.
Look im not saying i want this. Im saying its gross and shitty but that YOU and I have the right be that way in our wills and this isnt the executors fault.
Too many people think the executor has more decision power than we like at times.
I don't know what is in the will, but I can certainly imagine it does include directives to reduce payments to the families. I do agree it is the executor's job to carry out the person's intentions in the will.