Top Five Questions Facing the Boston Celtics this Offseason

Alec McAfeeCorrespondent IJune 17, 2009

BOSTON - MAY 17:  Rajon Rondo #9 and Ray Allen #20 of the Boston Celtics talk as the Orlando Magic shoot a free throw in Game Seven of the Eastern Conference Semifinals during the 2009 NBA Playoffs at TD Banknorth Garden on May 17, 2009 in Boston, Massachusetts. The Orlando Magic defeated the Boston Celtics 101-82 to advance to the Eastern Conference Finals. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement.  (Photo by Elsa/Getty Images)

Coming off a disappointing finish in the Playoffs, the Boston Celtics have many questions that need to be addressed in order for them to continue their current success.

Here are five questions the Celtics will have to face this offseason in order to contend for another NBA title.

1. The Future of Ray Allen

Ray Allen has been an integral part in the Celtics' success over the past two seasons, but he is due $19.7 million next season and he's not getting any younger—he turns 34 next month.

There are a couple things the Celtics can do: they can trade Allen along with another player for younger, more cost-efficient players or Boston could keep Allen and hope to improve through free agency and the draft.

The Celtics should look to deal Allen, seeing as he still has some value among NBA teams that are in the trade market.

The Celtics could trade Allen to the Oklahoma City Thunder for Thabo Sefolosha and the rights to the Thunder's second first-round draft pick—No. 25 overall.

With that pick, the Celtics could address their need for another wing and select either SF Terrence Williams (Louisville) or SF Sam Young (Pittsburgh).

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Both Williams and Young bring a level of maturity that is ready for immediate NBA action and learning from Paul Pierce and Kevin Garnett would help them immensely.

Getting rid of Allen for Sefolosha and a first-round pick would save Boston about $13 million next season alone. That would allow for more aggressive spending in free agency or cash to sign current players to longer deals.

2. Draft Status

Assuming the Celtics made no moves prior to the draft, the only pick they would have would be the No. 58 pick overall in the second round.

The Celtics are in dire need of another aggressive and athletic shooter off the bench to complement Tony Allen's defensive prowess and Leon Powe and Glen Davis' rugged styles.

One player that is expected to be available at this position is Kentucky shooting guard Jodie Meeks.

Meeks is perhaps the best pure shooter in this class and has an unbelievable body that should be able to hold up over the course of a demanding NBA season.

This is a low risk, high reward situation because there is no guaranteed money being discussed in the second round, so the Celtics could insert Meeks in the lineup for a "tryout" of sorts.

Meeks could replace Ray Allen in the lineup if the Celtics part ways with him—as they should.

If the Celtics were trade to Allen to the Thunder as I stated they should, the Celtics could potentially use that first-round selection on another big man with potential and then draft Meeks in the second round.

A player like Taj Gibson (USC) or DeMarre Carroll (Missouri) could give the Celtics much-needed athleticism and length in the post, something that Leon Powe and Glen Davis simply do not offer.

A Gibson/Meeks combination would excite an already lively fan base and would be viewed as a successful draft for the Celtics.

3. Free Agent Targets

If the Celtics were to deal Allen, there would be a major decision to make: with the extra money do you sign additional players through free agency or do you lock up current players for the future?

Say the Celtics dip into the free agent market; they would be looking for a scoring wing and an athletic big man and there are plenty of each available this offseason.

Ben Gordon and Trevor Ariza both are wings who can put the ball in the hole and would fit the Celtics' budget without Allen in town.

Gordon is a proven scorer who can demand constant attention, freeing up Pierce for mid-range looks and Garnett for his patented fade-away jump shot.

Ariza is a player who burst onto the scene this season with the L.A. Lakers by playing lock-down defense and consistently hitting open jumpers.

As far as post players go, Chris Andersen and Hedo Turkoglu could fit what the Celtics are trying to do.

Andersen is the prototypical big man the Celtics are looking for, while Turkoglu is the "home run" type signing that could energize an aging franchise.

Andersen is as athletic and exciting as they come and would probably be available at a very cheap rate—$4 to 6 million—while it would probably take all the Celtics' cap room to sign an All Star-caliber player like Turkoglu.

Either way, the Celtics could benefit from signing players through free agency.

4. Signing and Re-signing Current Players

If the Celtics did not want to sign through free agency, in fear of not having much room for the stellar 2010 free agency class, they could always lock up players to long-term extensions.

A player like Rajon Rondo has really improved over the past couple years and only has two years left on his deal.

This may seem like a long time, and it is, but Rondo is only getting better, so the earlier the Celtics sign him to a long deal, the less it is going to cost them.

The Celtics also have players of their own that are eligible for free agency.

Both Glen Davis and Leon Powe are restricted free agents and will need to be resigned and Eddie House is an unrestricted free agent and is available to sign with any NBA team beginning at the end of June.

The Celtics are definitely going to have to spend some money on some of these players because they can not afford to lose all three if they want to sustain their level of play next season.

5. Future Team Expectations

The Boston Celtics will most likely return all of their key pieces from a team that has won an NBA title and made the playoffs twice in the last two seasons.

It appears the Celtics have cooled on trade talks with teams about Ray Allen and Rajon Rondo and they are looking to build towards the future through the draft and free agency.

Team chemistry will be high, especially now that "The Big Three" are all on their last legs. Ray Allen, Paul Pierce, and Kevin Garnett will all have the type of focus and determination that they had when they won the 2008 NBA Championship and the expectations will be similar.

Fans should expect another playoff berth, and perhaps another trip to the Eastern Conference Finals.

Unless Ray Allen is dealt and draft picks are gained for this year's draft, I would not expect the Celtics to continue their success past next season.

The Big Three will all be declining in ability and rising in age and Rajon Rondo is not the type of player to put a franchise on his back.

It should be an interesting off season to say the least and the Celtics are just one of many teams who should make it interesting.