Adam Kaufman

What is the Biggest Question Facing the Celtics this Offseason?

Danny Ainge Rajon Rondo.jpg

You might be thinking, “What questions aren’t the Celtics facing this offseason?”

There are tons, many dealing with current personnel, existing and soon-to-be free agents and, naturally, what to do with a pair of first-round draft picks on or in advance of June 26.

[If you’re curious, we’re happy to tell you who Boston should select with pick No. 6 and No. 17. The national media has weighed in as well.]

Once again, we assembled’s panel of Celtics insiders to offer their thoughts on the biggest question of the many facing the franchise this summer.

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Gary Dzen: Can I be super boring here? While the decisions to keep/trade the No. 6 pick, go after Kevin Love, and keep/trade Rajon Rondo are sexier, in my book the biggest question facing the Celtics is whether or not to bring back free agent Avery Bradley. The reason? Those other three decisions are dependent on a variety of contingencies. Of course the Celtics WANT to trade for Love, but it probably isn't up to them. Same with Rondo, who the Celtics COULD reasonably trade for a collection of picks and All-Stars in theory but likely won't in practice. The No. 6 pick? You'd be crazy to even consider parting with it unless you're moving up, IMO.

That leaves Bradley, 23-years-old and a potential starter for years to come. Bradley has a $3.581 million qualifying offer but will command more than that in a long-term deal. He's said recently that Boston is where he wants to be. It's up to the Celtics, then, to decide whether or not he's worth the money to keep him here long-term.

My vote would be yes. Even if the Celtics draft a guard who eventually supplants Bradley in the starting lineup, you want that defensive-minded third guard coming off the bench. He's a high-end glue guy, worth a few extra bucks so long as it doesn't break the bank.

Jeremy Gottlieb: As the Celtics' rebuild continues to unfold this summer, Danny Ainge and company must decide how comfortable they are with the speed of the process. If they feel as though they can wait a couple more years to potentially threaten in the Eastern Conference, which would almost undoubtedly equate to at least one more potential 50-loss season as well as the likely departure of Rajon Rondo in free agency, then they should keep both of their first-round picks in next month's draft and continue to develop their young players. If they want to speed up the process in an effort to contend in the East in 2014-15, they need to package some of their truckload of draft picks over the next few years with a player or two and make a deal that will help them win more games right away.

Forgive me for butchering one of the most famous lines in the history of the written word but, "To wait or not to wait? That is the question." Celtics fans should have some semblance of an answer within the next month or so.

Adam Kaufman: There are a plethora of questions facing the Celtics this summer, but the most important ones surround the future of captain Rajon Rondo. For the C’s to choose their direction for the next few seasons, they must first decide what to do about their All-Star point guard.

Rondo is one year from free agency and likely views himself as a max-contract player which, to this point, he isn’t. That doesn’t mean he couldn’t receive such a deal but, only months removed from returning from a year lost to an ACL tear, he has much to prove before the Celts or any other team should go all-in for his services over the next several seasons.

As president of basketball operations Danny Ainge is well aware, Rondo wants to win. The pass-first veteran has already alluded to an interest in exploring free agency for the first time once he’s eligible and he’ll certainly want to be somewhere he can chase his second ring while he’s still in his prime. That being said, many close to Rondo have said he doesn’t like change and he does in fact want to remain a Celtic. Like Paul Pierce, he’s believed to want to be part of the group that takes this franchise from the bottom of the NBA to Banner 18.

For that to happen in the short-term, Ainge will have to deliver on those “fireworks” we keep hearing about, whether in the form of Kevin Love or another substantial acquisition in the quest for a new New Big Three. And it only starts there. What we witnessed in 2007 is the exception, not the rule. Otherwise, it could take a handful of years, multiple successful lottery picks and, potentially, an aging Rondo running the floor when all is said and done.

It’s time to either build around Rondo with veteran talent, or go through a full-scale rebuild (scary thought). If the latter is the case, it’s probably better to deal him for more assets. I’m not sure the Celtics will be able to have it both ways.

Brian Robb: The biggest question facing the Celtics for next season is a simple one in my estimation: How patient will the team be this summer with their rebuilding?

Right now, Danny Ainge and the rest of the Boston front office probably WANT to take a major step forward in this department. They would love to bring in an All-Star player like Kevin Love and turn the Celtics into a playoff team that is on the rise next season. Whether that ends up being a realistic possibility is probably beyond the team's control though. Will the Wolves decide to deal Love this summer? Will Love send signals that he wouldn't mind coming to Boston? Will Boston have enough to outbid Love's other suitors and appease the Wolves' demands? We don't know the answers to these questions yet.

No matter what happens with Love, the team's answer to the scope of the rebuilding question will have a large impact in shaping the entire roster this offseason. If any Love possibility is off the table, does Ainge still want to target a couple big-name veterans on the market that can help this team now and speed up a rebuild? In that case, valuable veterans like Brandon Bass, Rajon Rondo and co. have a much better chance of sticking around. If the team opts to stay patient with the rebuild and go young with their draft picks, moving the older veterans, including Rondo in a trade is a very real possibility.

The Celtics will explore both of these paths. The patience level of Ainge and the team's ownership on the idea of a long-term rebuild will be a major factor in determining what path they end up taking.

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