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Here's where having friends around the league could help Gay if he becomes a free agent. Gay has a long-standing relationship with Boston Celtics point guard Rajon Rondo, and Rondo has advocated for Gay coming to Boston in the past, as Gay told Marc J Spears of Yahoo! Sports:
It’s hard to talk to [Rondo] because he is always saying, ‘We need you over here. We need you over here,’ " Gay said. "So it’s not easy talking to him. But he’s being a friend, just telling me about keeping everything together and he makes you feel like you are still valuable.
One would assume that the Celtics are prepared to placate Rajon Rondo however possible in advance of his possible 2015 free agency.
The only real issue here, other than maybe Boston's actual desire to acquire an average defender and inefficient scorer, is that signing Gay to a deal that extends beyond Rondo's deal seems awfully dangerous.
If Gay were to leave Sacramento and the $19.2 million owed to him next year, you would have to assume he'd be looking for more long-term financial security and not a smaller one-year offer in the range of $7-8 million. That's right about what Gay is probably worth, but it's also in the neighborhood of what Boston can actually offer in free agency.
Perhaps a more likely scenario than Gay opting out and then signing with Boston would be for both sides to negotiate a trade. If Sacramento knows it can't keep Gay, turning him into something of value makes sense.
For Boston, dealing a salary that's on the books beyond 2015 (in order to clear more cap space) would make a lot of sense, and there are two forwards in Gerald Wallace and Jeff Green who fit the bill, along with decent-sized expiring players like Brandon Bass and a big leftover trade exception to utilize.
While Wallace would absolutely need draft-pick sweeteners attached, Green is a great starting point, even if it's hard to see Gay being an upgrade over him.
Boston has bigger fish to fry right now in its pursuit for Kevin Love, so it's unlikely this is something that would be in the works as a first priority.
Still, if Boston misses out on Love, this could potentially work if Gay accepts his player option, with Boston shedding future salary in exchange for Gay's massive one-year deal. Then, the Celtics could pair Gay with Rondo on the cheap, while general manager Danny Ainge brings in a star to join them.