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If ownership won't give Jack the resources to close a big or even medium salary deal midseason, it doesn't matter what kind of brilliant negotiating plan A-B-C or Z he has. No money = no leverage if you're a buyer.
That being said, he should ideally know how far ownership is willing to go, and be focused on realistic deals within those constraints - not out kicking the tires on players he can't afford and wasting other teams' time to the point they are complaining publicly about it. But, if ownership is being non-committal to him, and telling him "maybe, let's see the details" on everything...you can't put the blame on him for taking a scattershot approach externally.
Either way, something it seems ain't right here...but it's impossible to know who's really at fault. Is Z a weak negotiator, or is he just doing whatever he can to try to scratch out a win with a weak hand? We don't know what's happening behind the scenes in Marinerville.