re: As an athlete, would you choose good contract + a ring or great contract +0 ring

Most likely I'd take the larger pile of money. I'd like to hear the definition of good and great money tho.

Minimum wage in the NFL makes you wealthy by normal standards... but even the best position players in the NFL often make a lot less than MLB etc

The cheat answer to this is to be a popular figure who wins a championship and transforms that into a post athletic career that still pays. The other obvious point is if the good contract still paid over 10 million a year and you're playing a sport like baseball where you can have a 15 year career that's better than a great NFL wideout who only lasts seven years.