A tricky thing to remember about the Boston Celtics' 2014 offseason is that it isn't really about the 2014 offseason.
Of course, Boston just spent an entire NBA season losing games with an inferior roster, with the main goal of landing a top draft pick in June. That fact makes it difficult to realize that major priorities may not be met for some time.
Gerald Wallace's albatross of a contract isn't expiring and, with two years remaining on it, will be difficult to move. Rajon Rondo becomes an unrestricted free agent with the 2015 offseason. Boston is still tied into $26.2 million worth of contracts for Wallace, Jeff Green and Brandon Bass next year. All of this certainly weighs on the 2014 offseason but must be dealt with in a more forward-thinking process.
What is Boston's biggest offseason priority
Because of that monetary holdover, plus Rondo's $12.9 million and a series of smaller contracts, the Celtics are already about $10 million away from the projected salary cap with a team that is roughly the same as this 2013-14 version.
A full year of Rondo will certainly help, as will a third-year leap from Jared Sullinger and some improvement in Kelly Olynyk's sophomore campaign. However, those things alone aren't helping Boston rebound from a season in which it is currently 31 games under .500. To make the postseason in the Western Conference this year, one needed to win nearly 50 games.
The point is that Boston's priorities this offseason are largely dependent on a bigger picture—presumably one that Danny Ainge, Wyc Grousbeck and perhaps Brad Stevens have in their heads. Rebuilding the Celtics isn't going to be a paint-by-numbers project. It can't be, given all the different facets, possibilities and contract-length restrictions.
There are caveats with nearly every predicted move we can make for Ainge and Co. We learned that during the summer of 2007 when Boston had a 38.7 percent chance of landing a top-two pick and wound up drafting fifth. However, Ainge quickly flipped the script on that offseason and landed Ray Allen and Kevin Garnett.
To say that Boston's biggest priority this offseason is to make a move at the level of one of those two is a tad unfair. Ainge had two lottery summers to work up the asset arsenal and nerve to make those deals. This time around, the request is for him to cut that period in half.
The sheer mass of Boston's media landscape—from The Boston Globe and Boston Herald, to WEEI and 98.5 The Sports Hub, to the countless blogs and fan-made pages filling up the Internet—makes it harder than ever for Ainge to do his job. Priorities can get tough to manage.
Priority No. 1: Thursday, May 20, 2014
Unfortunately, the first priority is a necessary evil for this summer's Boston Celtics. On Thursday, May 20, the probable start date for the 2014 conference finals, Boston will have to be represented at the NBA's draft lottery.
This isn't a place anyone should want to be. However, it is still entirely possible to make a fool out of oneself or one's franchise at the event. The lottery should be treated with a cold demeanor no matter where your pick lands, not celebrated after putting your fans through a grueling season of consistent disappointment and tanking talk.
In 2007, Boston sent Tommy Heinsohn as its representative to the draft lottery. However, with Heinsohn having great difficulty traveling these days as he approaches his 80th birthday, Boston will likely look elsewhere.
The cold demeanor obviously brings to mind new head coach Brad Stevens. However, I'm not sure Boston wants to subject him to the misery that could go along with sitting behind those lecterns and being asked uncomfortable questions. Likewise, going the young player route is a hollow gesture. Subjecting a rookie like Kelly Olynyk to that same thing is a bit cruel.
Ainge is very much a likable face at the forefront of Boston's front office, as is Grousbeck. However, both may view themselves as above the makeshift theatre of May 20. They should feel that way, too. Franchises shouldn't make a spectacle out of being horrible enough to be on that stage.
Instead, Boston will likely send one of the background front-office players. Assistant GM Mike Zarren is an option. As is Austin Ainge, Danny's son and director of player personnel. The other route is a dangerous one. Sending Cedric Maxwell, Boston's radio color commentator and the likely successor to Heinsohn's TV throne, seems the most likely route if Boston is trying to make the thing watchable for its fans.
Priority No. 2: Thursday, June 26, 2014
After another month or so of scouting and speculation, the time will come for Boston to make its ultimate decisions. With two picks in the first round (none in the second), the Celtics will have a lot of options. Lottery night will tell them where that first pick will come, which should have a major effect on the route they take.
If Boston's lottery luck strikes out like in 2007, it may look to move up in the draft, pairing both first-rounders for a higher selection. However, with the projected top three picks as promising as they are this summer, it will be difficult to convince another lottery team to part ways with one of those higher slots.
What it comes down to ultimately is not screwing up. Boston either has to come out of this draft with two legitimate NBA players or a trade that grants them future assets or financial flexibility.
Drafting a bust, particularly early in the first round, could set back this rebuild another year. It took the Portland Trail Blazers years to recover from Greg Oden. The Minnesota Timberwolves are still searching for a playoff berth after taking Ricky Rubio and Jonny Flynn ahead of Stephen Curry in 2009. At this point, the Cleveland Cavaliers are too easy of a mark.
The Celtics may not wind up with Jabari Parker, Joel Embiid or Andrew Wiggins, but that doesn't mean they will have lost the draft and will have to lose for another year. As long as they come out of June 26 in the positive, Ainge has the ability to fill in holes and explore other avenues later on.
Priority No. 3: The Avery Bradley decision
In July, the NBA's free-agency period will begin, and the first thing on Boston's mind will likely be Avery Bradley.
Ainge, along with anybody who has an interest in Celtics basketball, has probably gone back and forth on what to do with the young shooting guard tens of times this season alone. Bradley started hot, slumped, got injured, came back hot, got injured again and is finally finishing strong.
Those good moments late in the season are of particular note because they are part of the small sample size we have of he and Rajon Rondo playing together. Despite being on the same payroll for four years, the number of times they have suited up together in the starting lineup is rather low in the double digits.
"Bradley is the perfect 2-guard for [Rondo], because he can get out on the wing and really create havoc running down the court."— Tommy Heinsohn (@CSNTommy) April 10, 2014
In early February, The Boston Globe's Gary Washburn calculated that it was just the 30th time the duo had started together. Since then, they have traded off-days and injuries that have likely kept that number under 50.
“Our chemistry is fine. He hasn’t forgotten how I play and I haven’t forgotten how he plays. It’s the same,” Rondo told Washburn. “We just know how to play the game. He knows the game of basketball. He knows when to make cuts. He’s just a smart player, and I think I’m a smart player, too.”
Bradley is closing the season on a tear, averaging 23.5 points on a 49.3/55.6/91.7 shooting split over the four games since his return from another three-game injury stint. Unfortunately, he has missed 21 of 81 games this year after missing 32 last year and a large chunk of the postseason in 2011-12.
Boston doesn't have the kind of financial flexibility that will allow them to keep Bradley at his projected requested salary. Instead, it has to rely on him realizing his personal potential may be greatest with Rondo and that at just 23 years old, there is plenty of time to make money.
Priority No. 4: Filling in the roster
Even if Bradley returns, the likelihood of Boston's starting lineup being made up of current Celtics seems slim. The team doesn't have a starting center, which was fine in a throwaway rebuilding year, but Boston is presumably going to be shooting for the playoffs in 2014-15.
With Rondo, Bradley, Green and Sullinger, there is somewhat of a decent core. I don't yet see Olynyk as a starting center, and while Bass started alongside Sullinger for a handful of games this past season, that wasn't a long-term solution. Kris Humphries is an unrestricted free agent, and Joel Anthony may be gone as well.
Pressey really, really needs to improve his shooting. But no doubting the man's vision and creativity.— Jay King (@ByJayKing) April 12, 2014
Possibly creating other holes are Jerryd Bayless and Phil Pressey, primary backups to both guard positions who are similarly free to explore their options this summer.
Boston might be able to seal up one or two of these holes on June 26. However, finding an immediate starting center in the draft is very rare.
In a strange turn of events, in order to fill in its roster, Boston may have to dismantle more of it. By dealing one of its forwards, it could alleviate a positional logjam to fill a hole with whatever return it can muster.
The bottom line is, after a year of uncomfortable rotations and difficulty distributing minutes properly, Boston has to give Stevens the tools he needs to succeed—or at least improve—in his second season. That means a properly acquired and set-up roster.
Priority No. 5: Entertain your dreams and keep the door open
Ainge may not have quite the arsenal of movable pieces he had in 2007, mostly because Al Jefferson was a singular talent. However, he does have quite the mixture of pieces, contracts and picks.
After some of the bigger moves he has been able to pull off with the Seattle Supersonics, Minnesota Timberwolves and Brooklyn Nets during his tenure, it is fair to allow him some leeway in exploring his own dreams.
While the Celtics go through this summer of drafting, building and blueprinting, it would be wise to maintain some flexibility on the off-chance that a major deal comes to the table—perhaps some of those fireworks that Grousbeck was talking about in Washburn's March 13 piece for Boston.com (subscription required).
If the opportunity to bring in Greg Monroe or Carmelo Anthony presents itself this summer, Ainge should have the freedom and confidence to make the necessary moves.
Boston went into the summer of 2007 praying for Greg Oden or Kevin Durant and wound up staring at the possibility of Jeff Green or Yi Jianlian after the lottery. However, Ainge's confidence and freedom allowed him to acquire Allen and Garnett and, in the process, Boston's 17th championship banner. He knows what the ultimate priority is.
Priority No. 6: Banner No. 18