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

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Just one ring? I'd take the money. If it's 100 million over 7 vs say 28 million over 7, you'd have to chip in 3 or 4 rings and I would have to be the hero in at least one of those seasons for me to even start thinking about it.

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Exactly. Taking less to win one ring as a scrub isn't worth it but if I take less to become a legend or at least a great then I'm in because I might have the shot to make that money back in endorsements and post playing opportunities.

Also, it's easier to do in the NBA or MLB because the contracts are guaranteed and even the "mid level" contracts are pretty awesome. I would have to think a lot harder before taking less just to be the 5th DB on the Patriots' 8th Super Bowl.