re: Is the Jrue Holiday situation somewhat akin to the Asik situation?

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Combined that with the fact that he's missed an average of 30 games a season since coming to NO and hasn't played 70+ games in a season since 2012-2013.

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He's had 1 serious injury that was intentionally mismanaged by the team which turned a 1 year recovery into a 2 year recovery and people act like he's Eric Gordon. We haven't heard about his leg since. Should the Warriors worry about locking KD up long term because he had complications and a longer than expected recovery time with his stress fracture a few years ago too?

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Any team that signs Jrue Holiday for $25M+ a season will be in salary cap hell

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The low $20s is a grey area to me. If they can get him for $22 I think that's good enough value that you can move him later if you need to, like if you go after John Wall. Start getting much above $22 and you're stuck with Holiday as your 3rd highest paid player for the foreseeable future.