re: 2016-2017 Realistic scenario for Upgrading Roster

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Not really that hard to understand once you realize that there is no tampering violations, in regards to the CBA,because Anderson IS a free agent and the fact that just because there's a moratorium for a week, prior to July 1st of the new fiscal year, doesn't mean that the conducting of prospective business is stalled.

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Teams get fined for even mentioning the names of Free Agents. He's a Free Agent, meaning any team is free to make a pitch to him. If a team like Sacramento thought they had a shot and don't even get their calls returned they should complain. Are the penalties available more than fines? I don't know, I suspect it's open ended. When Minnesota made an illegal agreement with FREE AGENT Joe Smith, the team got fined and stripped of multiple 1sts. LINK

What you're suggesting is technically possible but violates league rules in a way that could bring harsh penalties. Would Ainge take that risk to sign KD? Maybe, but not for Anderson. Therefore your whole premise is invalid.