Keep in mind, I don't give a rats behind if he retires or not, if he turns himself into a vegetable chasing some legacy or playing a game he can't let go of then that's on him.
That said, if a friend were to come to me and ask me my opinion on it and they were in the exact same position, I think my suggestion would be to strongly consider it, even if they hadn't won anything or had the money he has.
Granted that all depends on what your life plans are. If you plan to never get married or have kids and want to go out in a blaze of glory, by god beat yourself to a pulp and sit in a care home with mush between your ears. However, if you plan on having a family on down the road, well you probably need to stop and think about things a bit more and decide what is going to be important to you 5, 10, 15, 20 years down the road.
Lets face it, there are guys all around the league basically lighting matches around a gas can every single night, eventually it's going to blow up in your face.