Insiders assess most-discussed contract of the offseason

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The deal is seen as far too generous for the player being paid, so confusion reigns in the level-headed circles and frustration spills over in the more passionate ones. The conversation continues until said player can either prove or disprove his respective worth (on a relative basis, of course).

Sometimes, before that contract can play out, it's worth probing for answers to the questions that seem to be driving so many so mad. That is the case now with the most-discussed contract of the offseason: The Celtics' signing of forward Jeff Green to a four-year, $36 million deal, which has a player option in the fourth season and could be worth about $40 million with reachable bonuses.

When the 26-year-old landed the contract after missing last season to have heart surgery to repair an aortic aneurysm, there was an almost universal sense of bewilderment as to how and why those smart basketball men in Beantown would cut such a sizable check given the circumstances. (The contract also reportedly does not include an injury exception.) Green has had his moments in the league, to be sure, chief among them averaging 15.6 points per game for Oklahoma City from 2007 until he was traded to Boston along with Nenad Krstic midway through the 2010-11 season for Kendrick Perkins, Nate Robinson and a first-round pick.

But conventional wisdom -- while not always the North Star in negotiations -- would have one believe that his mediocre performance in the three-plus months with the Celtics in 2011 coupled with his medical history would have put him in a position of weakness as an unrestricted free agent. Instead, his agent, longtime power broker David Falk, said during the process that "12 to 14 teams" were interested in Green and the Celtics, like it or not, ultimately agreed to his terms.

In an attempt to satiate those still scrutinizing this contract, spoke to three league insiders (Falk, an Eastern Conference scout and a rival general manager) who shed light on Boston's rationale, Green's true value and more.

"Like most deals, there will probably be people who think that he was overpaid. I always feel he could have got a little more money, but because Jeff had such a strong feeling about returning to Boston, he [did this deal]. I feel that if he would've told me, 'I don't care where I go, just get me the most money,' then he probably could've gotten $11 or $12 million a year.

"Because Boston withdrew the [one-year, $9 million] qualifying offer in January, he became an unrestricted free agent six months before everybody else. We had a lot of discussions with people. No one should [discount] it when I said we talked to 14 teams. Some were serious, some were inquiries, and I definitely feel we could've gotten him more money."

"I thought the contract was a lot, just because of his condition. But the Celtics' situation, if they lose Jeff Green for nothing, then how do they fill that spot? It wasn't going to give them any more cap space. They weren't going to spend that money on somebody else, so they had to find a way to keep him. If their number is $10 million, then that's just what the number it is. If somebody else is offering him $9 million and he goes, then you lose that asset with nothing to replace it.

"The thing for me is that if you're a team with cap space, then you don't want to go out and use it on Jeff because for that kind of money, you're looking for somebody who can have a huge impact. But if you have him on your team, he's the kind of guy you don't mind spending money on to keep because he's a valuable part of what you're building."

"This is exactly why you don't make trades like this, because David Falk [had leverage] on Danny Ainge the way [agent] Rob Pelinka had it on [Nets general manager] Billy King" during negotiations that led to forward Gerald Wallace's signing a four-year, $40 million deal over the summer. "Wallace's market value was probably what Jamal Crawford's was, right? A little bit, like 20 percent, above the mid-level exception, maybe over a three-year deal? But because you ended up giving up the sixth pick in the draft to get him, you've got a gun to your head. You can't let the guy walk, so you're playing poker and you can't bluff because you're going to look like an imbecile if you gave away the sixth pick in the draft to rent a guy for 20 games during a lockout season when you weren't going to make the playoffs.

"It's the same thing with Jeff Green. Go back to that deal that Danny made. He made a deal for Nenad Krstic, who's now in Russia; Jeff Green, who missed a season with a heart condition; and the Clippers' pick, which was supposed to be this jewel of a pick but ended up being 22nd. Out of that deal, getting Jared Sullinger -- if he can stay healthy -- is probably the best asset. [The Celtics drafted Sullinger at No. 21 with their own pick and Fab Melo at No. 22 with the pick from the Clippers.] But if that doesn't fall in his lap, because of Sullinger's medical issue, then what is he getting at 22? And it's all for Kendrick Perkins, who helps Oklahoma City get to the NBA Finals.

"You're talking about a guy who you're now making a part of your future who Oklahoma City knew they couldn't win a championship with. He doesn't have a position. He doesn't rebound it well enough to be a power forward, he doesn't shoot it well enough to be a small forward, he isn't quick enough to be a small forward, so you can't replace Kevin Garnett and you can't replace Paul Pierce. So not only do you overpay him, but you don't get an [injury] exclusion on the heart?"

"You know that in a short period of time, Garnett, Pierce and [former Celtics guard Ray] Allen are all going to be gone. One year, two years -- they're not going to be there long term. And at that point, knowing that, you really have two options if you're Danny Ainge. One option is to move the team, trade [Rajon] Rondo, and start all over again. But if you believe that it takes three stars, three core players to create a championship team, and you know you have a 26-year-old Rondo, who is tremendous. If Jeff Green can be the second leg, and you can keep him, you're two-thirds of the way home. You don't have to nuke the team. So he represents a very strategic decision by the Celtics of how to manage the post-Big Three transition. Do you go to the bottom and start again, or do you try to keep it going?"

"These are clearly all win-now moves. With what Danny has in place, and if they all perform as expected and stay healthy, it's reasonable to think that they'll be playing Miami again in the Eastern Conference finals. Green has a bunch of money in likely bonuses, and a bunch more in unlikely bonuses. If they win a championship, it's $1.5 million. If they get to the Finals, it's $750,000. If they get to the conference finals, it's a half million. They'll have success, and his deal will probably wind up being worth $10 million a year."

"When Dallas won the title, I think Jason Terry was making more than that as a sixth man. [Terry made $10.6 million in 2010-11.] It all depends on the role in which they want to use him. If Jeff has to be a starter to justify his salary, then he's not going to be successful. You could have your No. 1 and No. 2 option, and then your third option could be coming off your bench. If Jeff gets in and they find a matchup that they like, he is their third guy. When Paul and Kevin retire, they have to get that big-time scorer to start -- whether it be a center or a shooting guard or something -- that they can rely on and where Jeff can fill in in that third spot. Jeff is never going to be a first or second option."

"Jeff acknowledges that he was way too deferential when he first got there because of the stature of the guys he was playing with. Now having watched the team for 16 months on the floor, and from the stands, I think he realizes that while they're great names and great players, for them to be successful, he's going to have to take a much more assertive role. I think Danny recognized all that in negotiations. So if you study, like I do -- I'm a student of economics and history -- and you realize that on virtually every one of the 16 playoffs teams, the top three players are all making approximately $10 million plus, I think what he got wasn't a record-setting deal and it wasn't a bad deal. It was a deal sort of right about where it should be."

"I don't think he's that badly overpaid at 100 percent health. I think it's a good contract. But throwing in the heart condition and not having an exclusion on a pre-existing condition to protect you? No matter what the doctors tell you, it's scary."

"[Boston's] own doctors assured the team that the risk of Jeff's suffering a recurrence of his injury is probably significantly lower than the risk of a player who never had it before suffering the same kind of problem. When the doctor in Cleveland did the surgery, he said Jeff would have had a bigger problem if he was coming back from an ACL than from what he had. The average person, when you hear heart condition, you have an emotional, visceral reaction. But the doctors worked hand in glove with Danny, and because Jeff spent most of the year in Boston -- almost the entire year; he was there all the time -- they were able to monitor him and realize that the emotional reaction was not an accurate indicator of the medical result of the surgery. He's 100 percent cured."

"It's not like it's a contract that they're never going to be able to trade if they want to go in a different direction. Every contract is tradable."

"But the problem from before is that when they did the Jeff Green trade, it was supposed to be sort of a one-foot-in-one-foot-out strategy, where you can still win but have your exit strategy away from the Big Three era in place. And I think pre-Jeff Green's heart condition, that was a reasonable player to go get. He's still a high-quality young player. He's not a max guy. He's not a mid-level guy. You can absorb that salary. But I think it's one of those deals where you can't get a little bit pregnant. Once you choose to give KG $36 million for three years and not trade Paul Pierce, then you give this deal to Green."