If he was the best lawyer at the best law firm in the country, and then one year later he was at one of the worst law firms making half as much money, EVERYBODY would agree that he had mismanaged his career.
Whether it was worth it or not, to become a better father, is between God and Timmy. But the career implications of it are pretty much not debatable.
I absolutely disagree with this statement. I'm an attorney and know quite a few attorney's who have left bigger, more prestigious firms to go to smaller firms or even to go into solo practice. They generally make less than half the money they did and almost all of them think it was a wonderful career move. There is motivation behind career choices that goes well beyond just the biggest/most prestigious/best firms and salary. There are time issues, pressure issues, expectation issues, area of practice issues and many others.
Tim may like less pressure, he may like Florida better than Massachusetts, who knows what else but all of those can factor into his career choices.
Additionally, you keep saying:
He currently plays for a garbage team for half the money he did in his last full NHL season.
While technically this might be true, it is at best misleading. His last full NHL season he made $5M this year his salary is $2.5M but he has $1.25M in bonuses, which are easier bonuses everyone seems to think he will easily meet (similar to the little doubt DeKeyser would reach his bonuses). With his bonuses he would be getting 75% of what he made his last full NHL season. Additionally, the 2012-2013 season that he sat out he was supposed to make $3M. Tim should be making $750k (20%) MORE than that this year. Also, you cannot over look the huge tax saving he is getting being in an income tax free state as opposed to a state that taxes income at 5.3%.
He may really like where his career is, he is making a lot of money, playing with very little pressure, warm climate. He may have made a perfect career choice for himself.