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Do you want Ray to stay?

It's a decision the Celtics' front office doesn't really have to ponder until the summer, but with Ray Allen set to become a free agent after this season, Boston must decide whether it wants to keep its Big 3 together for at least one more season (presuming, of course, Paul Pierce doesn't opt out of his contract early) or start an overhaul of an aging roster.

Allen, who will turn 35 in July, discussed his own NBA mortality during Allen Iverson's brief retirement, but has also often said he's in the best shape of NBA career. While his scoring average and 3-point accuracy are down from past seasons, Allen continues to log quality minutes and is as integral to the success of this team as ever.

Like the addition of Rasheed Wallace, you can't help but wonder if signing Allen to a multi-year extension makes long-term sense. The productivity might be there now, but what's left in the tank in three years (the length of Wallace's current contract)?

The best general managers in sports have to make tough decisions like this on a regular basis. While now is probably not the opportune time to point it out, the New England Patriots were the NFL's team of the decade in large part because of the shrewd personnel decisions the team made in order to remain a top competitor over the long haul.

Put yourself in Danny Ainge's shoes and suppose the Celtics win another NBA title in June, what should management do? Bring back Allen, committing quality money over what would likely be at least a two-year period? Or recognize that you squeezed two championships out of a three-year window with this new Big 3 and start the turnover process, potentially using the savings to try to lure a quality young player out of a bountiful 2010 free-agent class?

Remember, too, that Rajon Rondo's contract extension kicks in next year, while Pierce has a player option for $21.5 million. The Celtics have already committed to $62.2 million for seven players, without even addressing Allen's contract (which calls for him to make $19.8 million this season). The Celtics are currently on the hook for $84.7 million this season, fourth most in the NBA (the Lakers are currently tops at $91.4 million, according to the numbers at HoopsHype.com).

Right now, Allen, his teammates, and coach Doc Rivers seem to indicate they'd like this marriage to continue. You'd probably expect to hear no different from those parties, especially when things are going well.

Peter May, who previously covered the Celtics for the Boston Globe, wrote on Allen's desire to stay in Boston for an article that appeared this week on Yahoo! Sports.

”It’s a great situation here,” said Allen, who has not missed a game this season and is second in scoring and minutes, both to Paul Pierce. ”I’m a loyal individual. I don’t look at it like, ‘what other teams have cap space and all that.’ My agent will keep me informed as to other potential situations, I’m sure. But this is what I know. My house is here in Boston. I want to do everything I can to make sure I stay here and finish my career out.”

There’s also an added incentive for Allen to try and work something out with the Celtics, beyond the basketball. His son, Walker, was diagnosed with juvenile diabetes during the 2008 NBA Finals and is treated at a world-class facility in Boston. Allen knows how critical that is; Walker had to be hospitalized just before a recent Celtics road trip, resulting in Allen nearly missing the Nov. 29 game in Miami.

”My family is comfortable here,” Allen said. ”My son with the diabetes, that’s important. Obviously, I want to be here.”

We opened our Celtics-Bulls game preview with a note about how the loss of even just one player from a team's nucleus can affect a winning situation. All of which should make Allen's contract situation one of the biggest story lines of next summer.