The Boston Celtics are in the midst of one of the most difficult tasks in all of team sports: making an NBA team a legitimate contender. Why so difficult? Because only a handful of NBA teams are ever genuine contenders in any given season, and those are the teams that have superstars, top 5-7 players in the game, as their best players. Contenders usually also have at least one or two other top 15-20 players. The surest route to getting such superstar is to have a very high draft pick, among the top two or three picks overall, in a year where superstar talent is available. By most accounts, the 2014 draft is such a year, so the best thing for the Celtics would be to “tank” and make it possible to grab up the sort of stud who could be the best player on 62-20 teams for the next decade. 

But one-third of the way through the 2013-14 NBA season, the Celtics are doing a dreadful job of tanking. Why that is and what that means for the immediate and long-term prospects for the team is the subject of this piece. First, however, some context. 

Rebuilding the Celtics in Context

Danny Ainge is overseeing the rebuilding project for the Celtics. It is his second rebuild, and the degree of difficulty is high. No matter what he does he may not succeed; it will require more than a little bit of luck. 

When Ainge made the deals for Ray Allen and Kevin Garnett in 2007, he officially completed his first “rebuilding” project, one that had been in existence for the franchise since at least 1992. Ainge did not luck into Garnett and Allen; he had patiently accumulated young prospects and expiring contracts to make each of the deals possible. It was some superior GM work on Danny’s part to convert the train wreck he inherited in 2003 to a contender by 2007.

After the summer 2007 trades, the Celtics now had a bona fide superstar in Garnett—a top-5 player as well as a top-15 player in Paul Pierce and a perennial All-Star in Allen. They were now contenders, or at least as long as Garnett and Pierce were close to their primes. For Ainge, everything would be done to make the team win in the here and now. There are only a few legitimate contenders in the NBA and once a team achieves that status it should do nothing to undermine its immediate chances.

Because the Celtics’ star players were over 30 in 2007, it was understood that the contender “window” would only be open for a brief time. It lasted four seasons, generating one title and a glorious season where the Celtics lost the 7th game of the Finals on the road. A 2009 knee injury to Garnett is arguably what kept the Celtics from winning three consecutive NBA titles from 2008-10. Before his injury, the 2008-09 Celtics were playing the best basketball in the league by a clear margin, and the best basketball of the “Big Three” era.

After the 2010-11 season, it seemed pretty clear that the window had just about closed. Garnett was only a shadow of the player he had been before his knee injury, though he remained arguably the best defender in the league. The lockout that occurred in the summer and fall of 2011 meant that Danny Ainge was unable to wheel and deal and commence the rebuild. During a lackluster 2011-12 regular season he pondered “blowing it up,” or at least trading Ray Allen, but elected not to pull the trigger on a trade deadline deal. 

Then something odd happened: the Celtics played inspired hoops in the 2012 playoffs, and took the eventual champion Heat to seven games. In particular the defense provided that season by Garnett, Rondo and second-year guard Avery Bradley put up numbers that had almost never been seen before in NBA history. Doc Rivers had no interest in a rebuild, nor did Garnett or Pierce. Ainge wanted to re-sign a rejuvenated Garnett who was a free agent, so Ainge went “all in” in the summer of 2012 to keep the team a contender for another year or two. This was drawing to an inside straight, but given the roster, the coach and the success in the 2012 playoffs, it was understandable. 

How did he do that? After inking Garnett to a three-year $30 million deal, he signed the atrophying Jason Terry to a three-year, $17 million deal. He signed Bandon Bass to a three-year $20 million deal. Then, when Ray Allen left to take a substantially weaker deal with Miami, Ainge traded three future second round picks to sign Courtney Lee to a four-year, $22 million deal. All of these moves only made sense if the Celtics contended. If they did not contend, then clogging up the payroll with long term deals for guys who were not even starting caliber players was a clunker move, that would tie Danny’s shoelaces together if he attempted to commence any rebuild before 2015 or 2016. 

End of Contention

Ainge rolled the dice and he lost. By the spring of 2013, the window of contention had been painted shut. Ainge’s best player, Rajon Rondo, had a serious knee injury and would be out until early 2014, at best. There was no way to know how good he would be upon return. Nor was there much reason to believe that Rondo was good enough to be the best player on a championship team. He fit the profile of an ideal No. 2 guy. That left Ainge with the hardest job of all for a GM: getting a player better, even much better, than Rondo on his roster.

To top it off he had a roster filled with difficult-to-move contracts and no capspace anywhere on the horizon to utilize for prospective free agents. The deals for Terry, Bass and Lee began to smell like month-old fish left on a counter. Moreover, the Celtics had a mid-first round pick in the 2013 draft, which was considered one of the weakest in years. To top it off, the drafts in 2014 and 2015 looked like they might be chock full of game-changing superstars, but the Celtics were unlikely to be crappy enough to get a top-3 pick.

This looked like another long rebuild, not the wonderful quickie rebuild like in 1969-72 when Red Auerbach corralled JoJo White, Dave Cowens and Paul Silas and built a terrific team that won two titles. Or the quickie rebuild of 1977-80 when Auerbach got Larry Bird, Robert Parish and Kevin McHale and built the 80s dynasty team. Instead, there was mediocrity as far as the eye could see. A reprise of the tortured years from 1993-2007 seemed possible, even imminent.

Begin the Rebuild

The good news for Ainge by May 2013 was that the team’s fall from contender status was obvious to Rivers, Garnett and Pierce. And since none of them had any interest in a rebuild it both forced Ainge’s hand and opened up opportunities for him. He parlayed Rivers into an unprotected 2015 first round pick from the Clippers. That will likely be a low first-rounder, but injuries could change that, especially in the hyper-competitive western conference.

With regard to Pierce and Garnett, he needed to find a team or teams to take their contracts. There was not a long list. It seemed that there might not even be a market for Pierce or Garnett, or at least a market where a rebuilding team could get anything of value in return. In fact, it is unclear if the list extended past one team, the Brooklyn Nets and its delusional gazillionaire owner, Mikhail Prokhorov—who apparently had not yet had the NBA salary cap explained to him. Prokhorov thought he was an inch away from a championship team and the addition of Pierce and Garnett was all that was needed. Ainge looked to the skies and thanked his lucky stars.

Ainge gave up Pierce and Garnett—two guys he really had no need for—and the worthless Jason Terry. In exchange he took back one very bad contract in Gerald Wallace—three more seasons at $10 million per—plus three other contracts that would expire after one season. One of these was for Kris Humphries, a serviceable big but vastly overpaid at $12 million for the 2013-14 season.

Why would Ainge make this trade? Look at what else he got: the lower of the 2014 first round pick of the Nets or Atlanta. Right now it looks like the Celtics will get Atlanta’s pick, which is presently in the 17-20 range. And that is just the beginning. The Celtics also get the Nets' unprotected no. 1 picks in 2016 and 2018. The Celtics also have the right to swap no. 1 picks with the Nets in 2017. 

This boggles the mind. The Nets are an old team. They do not have their own first round pick again until 2019. (Atlanta has the right to swap first round picks with the Nets in 2015.) They are way over the cap. Their management seems to have graduated magna cum laude from the Donald Sterling-Ted Stepien Leadership Academy. They are poised to be declining in two or three years, if not sooner, and have little recourse to improve their situation for the balance of the decade. Some or all of those three no. 1 picks the Celtics will be getting from the Nets from 2016-18 stand a decent chance of being lottery picks, even high lottery picks. 

So Ainge parlayed Garnett, Pierce and Rivers into four additional unprotected no. 1 picks—and a right to swap picks in 2017. In early May it looked like he might get nothing for nearly expiring assets. 

Oh yeah, there is one additional important return for the deal: The Celtics get a $10.2 million trade exception through June 12, 2014. This can be used in a number of ways, not the least of which is to swallow a bad contract in exchange for a no. 1 pick. So, for example, if the Lakers want to clear space to make a run at two bigtime free agents in the summer of 2014, they could trade the final year of Steve Nash’s contract to the Celtics ($9.7 million) to the Celtics and the Celtics could get a distant no. 1 pick for doing so.

Red is smiling down on Danny. Good work! 

Look Out Below! Tank Time!

Almost immediately all talk in Celtics Nation was about the need for the Celtics to tank in 2013-14. Rondo would miss much of the season. And the 2014 draft looks like one for the ages. There are a good 5-8 players who would be legitimately in play for top-two caliber picks in the majority of years. This was a great year to tank because even if you whiff with the lottery balls, the 5th or 6th pick overall might still net a superstar.

There is a lot of confusion about tanking. It does not mean that a coach tries to lose and that the players try to lose. It means that all personnel decisions are made with an eye to the future, and nothing is done to enhance the immediate prospects of the team. Good veterans who will not be around in two or three or four years have no role to play so they get traded or benched. A team plays young and inexperienced guys who will likely lose, even trying as hard as they can to win. But if the team does ever contend, these are the players who will be on that team. The coach will work hard to install his system and teach the players to play properly; he is not trying to allow bad habits to form. This was how the Celtics tanked in 2007, after Pierce went down with his injury. As one who watched nearly every Celtics game that year, I can state that it was an entertaining team.

This seemed like the likely course for the 2013-14 season. Three problems emerged in the first six weeks of the season that may have tanked the prospect of tanking. 

First, in replacing Doc Rivers, Ainge went out and hired the person he considered the nation’s finest college coach, the thirty-something Brad Stevens of Butler. In a revealing interview just before Ainge hired Stevens he said that there are few coaches in the NBA who were so great they could actually elevate marginally contending teams into champions. Ainge termed them “Michael Jordan” coaches, and indicated that any team would want a coach like that. Ainge then went out and signed Stevens, who took Butler to two consecutive NCAA title games. The roster on his 2011 team was bereft of talent—more than one observer noted there were few Big Ten teams with less talent—but there Butler was playing UConn for the championship. Ainge signed what he believed to be a Michael Jordan coach, or someone with that sort of potential. Those type of coaches are obviously not ideal for a tanking.

Second, Ainge’s roster cupboard was not bare. There were a number of intriguing young players like Jared Sullinger, Kelly Olynyk and Vitor Faverani to go along with young starting talents like Avery Bradley and Jeff Green. And there were holdovers like Bass, Lee and Jordan Crawford too. A third of the way through the season it is clear that most of these guys are average to above-average NBA players. Sullinger as age 21 has the ability to be an All-Star, or at least an above average starter. Whether it is due to Ainge’s talent judgment or Stevens’ coaching or a number of other factors, what is striking is that most of the players are playing as well as they ever have. The team is well coached, and the players are buying into Stevens’ program. It is not going to go 22-60. And that is before Rondo even returns to action.

Third, the Eastern Conference royally sucks. It is atrociously bogus. Some teams, like Toronto and Philadelphia, are indeed tanking. Some teams have piles of injuries and some are simply bad. But a team could conceivably go 36-46 and still make the playoffs. It looks like the Celtics are probably in the playoffs, barring unforeseen injuries. And if the Celtics do miss the playoffs, they likely draft between 8th and 10th overall.

Is there a Plan B...or Plan C?

So if tanking is off the table, if the Celtics are not getting a high first round pick in 2014 or in the visible future, can they ever get the superstar necessary to contend? After all, most the guys who are the best player on championship teams were drafted in the top three and usually first or second overall. 

Have Danny Ainge and Brad Stevens cooked their own gooses? Will Toronto and Milwaukee and Utah and Philadelphia all be laughing at them when their superstar-led teams are contending in a few seasons and the Celtics are mired in the purgatory of endless 48-34 seasons? Visions of teams like the 1980s Milwaukee Bucks and 1990s Indiana Pacers come to mind. Regular season battlers; playoff clunkers.

In one sense Ainge has his bases covered by trading for future unprotected first round picks. He may well get his cake and eat it too if the Nets flatline. Don’t forget that the draft picks that brought Magic Johnson and James Worthy to the Lakers were from similar trades for unprotected first round picks many years down the road.

But there is a much greater chance the Nets will not provide a high lottery pick.

And, of course, there is always a chance that Ainge could strike gold with a pick at the end of the lottery or in the mid-first round. That is where Paul George, Kobe Bryant and John Stockton were drafted. But those sort of picks happen once every 15 years or so. So look for that again around 2025. At any rate, it is nothing to plan around.

What then? 

This is where the changes in the NBA’s collective bargaining agreement comes into play. With the maximum contracts and the shortened length of contracts, superstars are far more inclined to move to new teams, and do so more regularly. Before the 2000s, superstars rarely moved from their first team, except at the end of a career. Consider, for example: Bill Russell,  Oscar Robertson, Jerry West, Elgin Baylor, Walt Frazier, Rick Barry, Larry Bird, Magic Johnson, Michael Jordan, Scottie Pippen, Isiah Thomas and Hakeem Olajuwon. And if they did move in their prime, it was usually at their demand and only once, as with Kareem or Elvin Hayes. 

Not so in the 2010s. Chris Paul, Carmelo Anthony and LeBron James have moved once, and odds are they will do so again. Dwight Howard already has moved twice. If Oklahoma City is not winning or Minnesota is not contending, Kevin Durant and Kevin Love will almost certainly wish to leave. It is the new world order.

Ideally a team like the Celtics could devote several years to shedding deadweight contracts so it might be in position to have the capspace to sign a maximum-contract free agent. That is how Houston got Dwight Howard. But this is actually more difficult than it seems. Free agents have to select a team voluntarily. And they are not going to voluntarily go to a lousy or even mildly decent team as a free agent since the money is the same wherever they go. Instead they want to go to a team that looks like it will immediately contend for a title. The sort of team that has lots of capspace is unlikely to be so positioned. 

And if a superstar is willing to pick a team for criteria outside of potential championships, it is usually a city with terrific weather and/or lots of glamour. Boston flunks that test. It will only attract superstars because it offers a chance to win and win big.

Danny’s dilemma

Nowadays, most superstars are traded before they hit free agency, so the team holding the contracts can get something in return. That is the likely way Ainge will get his next superstar, as he did with Garnett in 2007.

To put the Celtics in a position to be attractive to a prospective superstar free agent, Ainge has to walk a very fine line. He needs a team that is competitive and promising such that a superstar will feel like he can immediately contend. Yet at the same time, Ainge has to resist the temptation to sign up a lot of supporting cast players to three or four years deals at salaries above the MLE level. These are players that are difficult to trade and that clog up capspace. They are the sort of guys who make a team permanently decent, but never a contender.

The dream scenario for Ainge is to have a combination of young talented players at rookie contract scale, guys like Sullinger and Olynyk and the 2014 draftees. He will want maybe one or two veteran guys on big time deals, who will complement the superstar. Rondo, in my view, is a sure thing to be extended for another four years. Whether Jeff Green remains past this contract is a decision that is very much up in the air.

The balance of the roster should be made up of players on expiring deals, or guys whose future seasons are unguaranteed. These players are very attractive as cap filler in making trades for superstars. (Regrettably, Courtney Lee and Gerald Wallace have no value—not because they cannot play but because they are so absurdly overpaid through 2016—and Danny will likely have to hold his nose until these deals expire.) In addition, Ainge wants to have future first round picks that can be used to sweeten trades for superstars. He has done what he can by accruing four additional first round picks between now and 2018. 

The dilemma Ainge faces will become more apparent in the weeks before the trade deadline. Three players in particular require hard decisions: Brandon Bass, Jordan Crawford, and Avery Bradley.

Bass is playing the best basketball of his career; he has evolved from a rotation player to a legitimate NBA starting forward. He has become a superb defender who can take on the top scoring forwards on the opposing team. He has gone from a player with little positive trade value to a player who could contribute to a contender. Bass also plays the same position as Jared Sullinger and Kelly Olynyk. He really needs to go, to create space for the kids. At the same time to trade Bass will almost certainly make the team weaker in the short-term. That is exactly the right thing for the Celtics to do, but it will still be a difficult move for many to accept. It will take cojones. 

Likewise, Crawford has been a revelation. Ainge basically got him for free last season and then decided to not to pick up his option for 2014-15. In an astonishing turnaround, Crawford looks like a legitimate solid starting NBA point guard. It is not much of an exaggeration to say that the Celtics would be 4-20 rather than 10-14 at the time of this writing if Crawford had not emerged as such a good player. Crawford  just turned 25 and this is his first season at his natural point guard position. He could get a lot better. At the same time, Crawford is not a shooting guard and he is still no Rajon Rondo. Moreover, he is an unrestricted free agent after the season. It makes no sense for the Celtics to re-sign him at the rate he is likely to attract. Those are exactly the sort of contracts the Celtics are wise to avoid for the time being.

It seems obvious: Crawford should be traded. He should net either a future first rounder or maybe the Celtics could get someone to swallow Courtney Lee’s contract, or both. But if the Celtics do not trade him before the deadline they will lose him and get nothing in return. That would be senseless, as the Celtics are not going to contend this year. 

Finally, Avery Bradley will be a restricted free agent in the summer of 2014. The Celtics can match any offer he gets. Bradley is a mind-blowing defensive player with an improving offensive game, though it has a long way to go to reach All-Star status. The Celtics need to think long and hard if they want to devote $32-40 million to Bradley over the next four seasons. It would really clog up the salary cap and make it more difficult to get the necessary superstar. If the answer is “no,” the Celtics might be best off trading Bradley before the deadline. The Celtics would be able to get considerable value for Bradley then. It would be ideal to have Bradley be part of the future of the team, but the new economics of the NBA might make that a short-sighted decision. 

Watching a GM build a contender is one of the reasons people flock to the RealGM website. Danny Ainge has built one champion and is committed to doing it again. The next two months will provide crucial insights into his strategic thinking.