Yeah in most cases I do, and I definitely would have told him to take that deal had he asked.
I think we romanticise sporting careers in ways we never would in other areas of life and decision making. Success is great and a nice bonus, but a premiership medal doesn't keep your house warm when you are 45. Working at a great club is nice too, but the reality is all footy clubs are fun places to work. You find similar characters in all of them, there's always a lot of laughs and a lot of mostly similar personality types in players who for the most part get on really well. The winning and losing side of it passes quickly and that ebbs and flows anyway.
If it was one of our kids and they had a choice between working at Coles and Woolworths, and one of them was going to pay them five times more, I don't think many of us would stop to worry about which one would have the most sales or greatest customer satisfaction ratings before telling them to take the deal.
Above all of that, the big factor in my mind is always that you are only ever a bad injury away from the end in professional sport. If Bolton's knee pops tomorrow, he could easily be out of the game by 26 years of age, with not much to show for it. I've seen many people end up in that boat so I always say if you can set up your life then take the chance.