Will Danny Ainge Opt for Expedited Boston Celtics Rebuild?

For Boston Celtics fans, it’s been hard to see the light at the end of the rebuilding tunnel in recent weeks. After team president Danny Ainge traded away star point guard Rajon Rondo to the Dallas Mavericks in mid-December, the team’s prospects for a speedy return to relevance appeared to take a step backwards.

That trend continued on Monday when the Celtics sent leading scorer Jeff Green to the Memphis Grizzlies in a three-team trade for expiring contracts and future draft considerations.

Instead of keeping his two best players and a potential recruiting tool for prospective free agents next summer, Ainge continued his strategy of compiling long-term assets that started when he dealt Paul Pierce and Kevin Garnett to the Brooklyn Nets in July 2013. The Celtics received a compensation package that included three future first-round picks in that deal. 

Eighteen months later, Ainge has amassed 11 likely first-round picks over the next five drafts by selling off more useful veterans and absorbing other teams' unwanted salaries.

With Rondo gone, one prospective path to relevance is to remain patient and hope young players with potential like Avery Bradley, Marcus Smart, Jared Sullinger and James Young develop into building blocks alongside Boston’s future draft picks. That’s a process that could take years and comes without any guarantee those players will be able to raise their games and morph into stars.

That uncertainty is exactly the reason why Ainge may have no inclination to follow a long rebuilding route in spite of dealing Rondo. Instead, the distinct possibility remains that the Celtics could be aggressive with their accumulated picks and projected salary-cap space as soon as this summer.

It’s unlikely the top names of the 2015 free-agency class would opt for Boston if similar money and a better chance to win now were offered elsewhere. However, younger free-agent names looking to earn their first major payday such as Greg Monroe, Paul Millsap, Draymond Green and Reggie Jackson could become realistic targets for Ainge via free agency or trade.

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How could the Celtics pry away said players from their current teams and other suitors? Let’s explore the assets the Celtics have built up and examine how they could aid the team in expediting this rebuild.

Asset Accumulation        

Just three weeks after the Rondo trade, Ainge made another batch of moves with an eye toward the future over the weekend. First, he flipped recent addition Brandan Wright to the Phoenix Suns on Friday. The Celtics acquired a conditional future first-round pick owed to Phoenix by the Minnesota Timberwolves in the deal.

The selection is top-12-protected for 2015 and 2016, and it turns into two Minnesota second-round picks if not conveyed by 2016. By trading Wright into Phoenix’s salary-cap space for no return player, Boston also received a $5 million trade exception in the deal. 

Ainge also shipped Green to the Grizzlies in a three-team trade involving the New Orleans Pelicans that became official on Monday. The Celtics received a protected future first-round pick from Memphis in the transaction, as well as salary fillers Tayshaun Prince and Austin Rivers.

Boston is reportedly already looking to trade Rivers in hopes of landing an additional second-round pick, according to Adrian Wojnarowski of Yahoo Sports. 

Ainge’s recent moves continue to create plenty of flexibility for the Celtics as they transition into the next stage of their rebuild. The only 2015-16 salary that Ainge has added in his three latest trades is a $2.9 million player option for Jameer Nelson.

That maneuvering almost ensures that Ainge will have significant salary-cap space in free agency next summer for the first time in his tenure with the Celtics, which dates back to 2002. Currently, the Celtics have just $38.5 million in salary commitments for 2015-16, while the salary cap is estimated to be at $66.5 million, according to Zach Lowe of Grantland.com.

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While creating an ability to spend big next summer, Ainge has focused almost exclusively on acquiring draft assets in his latest dealings. Over the last month, he added at least four more picks to his impressive stockpile of selections compiled for the next five drafts. 

Here’s a quick summation of the team’s current draft inventory.

First Round: BOS, LA Clippers, MIN (top-12-protected), PHI (top-14-protected), DAL (protected 1-3, 15-30)

Second Round: BOS, PHI (Celtics receive pick if PHI 2015 first-round pick is not conveyed), WAS (top-49-protected)

Overview of likely picks conveyed: Despite owning five potential first-round picks, the Celtics are projected to receive just two in 2015 due to pick protections. The Clippers' pick is unprotected and was acquired in June 2013 in the Doc Rivers “trade.”

The other picks (Wolves, Mavericks, Philadelphia 76ers) are all expected to fall within pick protections based on each team’s current place in the standings. If those placements hold up, they will roll over to the 2016 NBA draft or turn into second-round picks (where indicated).

First Round: BOS, BKN, CLE (top-10-protected 2016-18, unprotected 2019), DAL (top-7-protected, owed if 2015 Dallas first-round pick was not conveyed), MIN (top-12-protected)

Second Round: PHI (conditional), CLE, MIA, MIN (if 2016 first-round pick not conveyed), MEM/DAL (higher of two selections)

Overview of likely picks conveyed: The Celtics are projected to receive four of the first-round picks listed. Both Cleveland and Dallas are expected to be playoff teams next season, so their picks will transfer to Boston if that holds up. The Brooklyn selection is unprotected.

The only question mark is the Minnesota pick. Given the team’s own youth and the toughness of the Western Conference, it’s difficult to envision them falling out of the top 12 in next year’s draft. If that's the case, Minnesota will give Boston second-round picks in 2016 and '17 instead of a first-rounder.

First Round: BOS (right to swap first-round picks with Brooklyn)

Second Round: BOS, CLE, MIN (if 2016 first-round pick not conveyed)

Overview of likely picks conveyed: The Celtics have the right to swap first-round picks with Brooklyn via a condition of the Pierce/Garnett deal. If the Celtics do exercise that provision, Brooklyn will be granted Boston’s 2017 second-round pick (top-45-protected).   

First Round: BOS, BKN

Second Round: BOS

First Round: BOS, MEM (expected)

Second Round: BOS

After sorting through the team projections and pick protections, the Celtics are likely to come out with a whopping 11 first-round picks and 13 second-round picks over the next five seasons thanks to Ainge’s dealing during the past 18 months.

Chances are the Celtics will continue to add to that stockpile if they attempt to deal other veterans on expiring contracts (Brandon Bass, Marcus Thornton) as the trade deadline approaches.

Seeing that NBA teams are only allowed to have 15 players on their rosters during the season, it’s fair to assume that the Celtics won’t be using all these selections. 

Will Ainge remain patient with his picks or put them to use in trades next summer? Let’s take a look at some of the potential avenues he can take with the rebuild.

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Draft Dealing

One simple way to reduce draft-pick volume is by opting for quality rather than quantity. The majority of the first-round picks Boston is currently owed are likely to land in the latter stages of the first round due to the quality of teams Ainge has traded with (Cleveland, Dallas, Memphis).

Ainge has a track record of finding some gems in the mid-to-late stages of the first round in recent drafts (Rondo, Tony Allen, Al Jefferson, Kendrick Perkins). All of those picks were made eight years ago at this point, and Ainge's recent first-round selections have included fewer hits (Kelly Olynyk, Jared Sullinger) than misses (Fab Melo, JaJuan Johnson, J.R. Giddens).

It’s difficult to trade up to the top of any NBA draft, and Ainge still doesn’t have the assets to do that. However, Boston has compiled enough excess picks now that Ainge should have the ability to deal away multiple first-round selections in order to move up in the first round of future drafts and target prospects that best fit the team’s rebuild.

Aggression in Free-Agent Market

On the surface, Boston’s prospects on the free-agent market appear limited. Yes, the team has cap room, but the same bodes true for several other teams. Beyond a well-respected young head coach in Brad Stevens and a rich franchise tradition, there is little else to lure potential building blocks to Beantown beyond dollars.

It’s hard to imagine top 2015 unrestricted free agents like Kevin Love, DeAndre Jordan and LaMarcus Aldridge leaving their successful franchises for a young, inexperienced roster in Boston. The same can be said about top 2015 restricted free agents including Kawhi Leonard and Jimmy Butler that are highly valued by their current teams.

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Beneath those emerging stars remains a second talented tier of free agents that could emerge as foundation pieces over the next decade. Restricted free agents such as Tobias Harris, Draymond Green and Reggie Jackson would be major upgrades to the Celtics lineup and should be looking for sizable paydays in their first free-agent contracts.

Teams have the right to match any contract restricted free agents sign on the open market, but Boston’s array of draft picks gives them the option of enticing teams into sign-and-trades. A future first-round pick or two may be enough to coax a team with a high payroll to send one of their young free agents Boston’s way.

Other potential free agents targets to watch for this summer include Goran Dragic, Wesley Matthews, Greg Monroe and Al Jefferson. Landing a couple of these kinds of players could enable Boston to make its way back into the Eastern Conference playoff picture next season.

The Celtics also have a useful building tool with their trade exceptions. Ainge landed a $12.9 million exception in the Rondo deal and just added a $5 million one after shipping Wright to Phoenix. Both of these exceptions allow Boston to absorb salary in a trade without having to send any out to its trading partner.

That’s a valuable weapon for Ainge to have if any notable names become available in a trade. For a franchise looking to trade an expensive player, the Celtics could absorb said contract while sending out significant draft-pick compensation in return. Very few teams around the NBA right now have both of those capabilities.

At this stage, all of these scenarios are just options. There’s no guarantee any appealing trades or free agents will emerge for Boston in the next couple seasons. However, we saw back in 2007 just how aggressive Ainge can become with his assets in the midst of the rebuild when he dealt for Ray Allen and Garnett that very summer.

Eight years later, the Celtics have the cap space and draft assets to make some noise yet again. With a head coach who’s hungry to win and an ownership team that’s willing to spend, don’t be surprised if the Boston rebuild moves a bit quicker than you expected.

All draft-pick and salary information from Basketball-Reference.com unless otherwise noted. 

Brian Robb covers the Boston Celtics for Bleacher Report. Follow him @CelticsHub on Twitter.