Danny Ainge always will be invincible in his executive role for the Celtics , riding on the goodwill that he earned from serving as the architect of the 2007-08 championship team. Ainge is the man who effectively swapped Al Jefferson , Gerald Green , Ryan Gomes , Sebastian Telfair , Theo Ratliff , Delonte West , Wally Szczerbiak  and three first-round draft picks for Kevin Garnett , Ray Allen  and a second-round pick that turned into Glen “Big Baby” Davis.
Ainge earned the NBA’s Executive of the Year award for the 2007-08 season, and looking back, his acquisitions look just as good as they did when he received that distinction more than four years ago.
Ainge hit on just about every transaction that offseason. First, he made the trade for Allen on draft day for Jeff Green , West and Szczerbiak. The throw-in to the trade was Seattle’s second-round pick, Davis, who arguably has had a better career than Green.
Ainge’s entire offseason followed the same trend. He pulled off the Garnett trade on July 31, nearly depleting the C’s roster with the goal of building a team around Garnett, Allen, Paul Pierce  and Rajon Rondo . Ainge began filling out the roster with complementary pieces such as Eddie House  and James Posey  that offseason. During the season, he acquired P.J. Brown and Sam Cassell, rounding out a championship roster from top to bottom.
Four-plus years after the Celtics’ championship run, Ainge has failed in repeating that feat with nearly the same exact core. Dissecting the president of basketball operations’ track record over the last four seasons, it is fair to say Ainge has missed more than he’s hit since the Celtics hoisted the championship trophy.
2008-09 season: Ainge kicked off the Celtics’ bid to repeat as champions by drafting J.R. Giddens with the 30th pick of the 2008 draft. Giddens played 38 games in his NBA career, only six for the Celtics. Of course, picking at the bottom of the first round is never an exact science for an NBA general manager. That being said, Giddens was the 30th pick. The 31st pick was Nikola Pekovic, who is averaging 14.2 points and 7.5 rebounds for the Timberwolves  this season. Picks 34 through 36 included Mario Chalmers  by the Heat, DeAndre Jordan by the Clippers, and Omer Asik by the Trail Blazers. Chalmers was the starting point guard for the NBA champion Heat last season. Jordan is averaging 10.4 points, 10.6 rebounds and 2.5 blocks in his career. Asik is averaging 10.9 points and 12.1 rebounds this season for the Rockets.
That offseason, Ainge also re-signed Tony Allen , House and Cassell in an attempt to run it back with the same cast of characters. He did, however, let Posey walk when the forward accepted a four-year, $25 million offer from the Hornets. Finally, Ainge signed Darius Miles to a non-guaranteed contract and waived him before the start of the season.
After the trade deadline, Ainge acquired Stephon Marbury  and Mikki Moore , hoping they’d provide a similar contribution to the one Brown made the previous season. Both players failed in that respect, and the Celtics fell to Orlando in the Eastern Conference semifinals.
The verdict: All in all, it was a below-average season for Ainge. Allen and House maintained their roles for the most part. Cassell didn’t make it through the season with the Celtics, getting traded to Sacramento. The good news for Ainge: Posey was overpaid by the Hornets, who later traded him to the Pacers, only to see him get amnestied by his new team.
2009-10 season: The offseason started with the Celtics drafting Lester Hudson  with the 58th pick. Hudson didn’t pan out, but neither did any of the players drafted after him. The big offseason acquisition was Rasheed Wallace , who played an entire year out of shape for the C’s before making a positive contribution in the playoffs. Still, at the end of the year, Doc Rivers  broke the news that Wallace was ready to retire, seemingly greasing the skids for the Celtics to get out from under the contract Ainge drafted for the big man. Wallace has since returned to the NBA, screaming “Ball don’t lie” in a Knicks uniform this season. Not the best use of Ainge’s mid-level exception. Ainge also signed Marquis Daniels  to fill the James Posey role. We can all agree Daniels never filled that role.
That February, Ainge acquired Nate Robinson  in a trade with the Knicks. Ainge’s post-deadline acquisition was Michael Finley . Neither Robinson nor Finley provided enough consistent support for a team that lost to the Lakers in the NBA finals .
The verdict: Ainge didn’t do enough to surround the Big Three in only their third season together. Wallace was a bust, Daniels wasn’t Posey, Robinson wasn’t House, and Finley wasn’t Brown.
2010-11 season: The offseason began for Ainge when he drafted Avery Bradley  with the 19th pick in the 2010 draft. Ainge continued the offseason by choosing the direction for the long-term future by resigning Pierce to a four-year deal and Ray Allen to a two-year deal. Ainge also resigned Robinson and Daniels. In possibly the worst signing of the last five years, Ainge signed Jermaine O’Neal  to the mid-level exception for two seasons. O’Neal played a total of 49 games in a Celtics uniform, never averaging more than 5.4 points per game. He earned his release before the playoffs in 2012 after expressing a desire to retire due to injuries. This year, he is back with the Suns, as a captain, averaging 8.2 points per game with a smile on his face.
Ainge also took a chance on Shaquille O’Neal  at the age of 38, albeit for the short money of about $1.5 million per season. While you can’t criticize Ainge for taking a chance on Shaq for that money, you can rip him for trading his starting center, Kendrick Perkins , at the trade deadline, in hopes that Shaq would produce at the level of Perkins in a replacement role. To no one’s surprise, Shaq got hurt at midseason and played only 37 games for the Celtics before retiring.
Back to the Perkins trade: Ainge moved the team’s starting center and emotional leader for Green, who has yet to consistently demonstrate his value to the C’s. The Celtics had the best record in the NBA at the trade deadline when they moved Perkins for Green and Nenad Krstic . Even after acquiring non-factors Troy Murphy  and Carlos Arroyo  after the deadline, the Celtics lost to the Heat in the Eastern Conference semifinals.
The verdict: Ainge pushed his chips to the table before the season when he extended Pierce and Allen. He added to the pot when he signed aging veterans Shaquille O’Neal and Jermaine O’Neal. Then, for some reason, when his team was in the top spot in the NBA at the trade deadline, Ainge abandoned the short-term mission and traded Perkins for a long-term investment in Green. It’s a theme that has been consistent over the last five years: Ainge retains his greatest assets but fails in his attempt to surround his core players with quality complementary pieces. Drafting Bradley is arguably Ainge’s best acquisition since being promoted to president of basketball operations in 2008. However, the 2010-11 season is arguably Ainge’s worst in that role.
2011-12 season: The Celtics started the offseason by selecting MarShon Brooks and E’Twaun Moore  in the draft. Ainge immediately moved Brooks to the Nets  for JaJuan Johnson . Ainge then signed Marquis Daniels, Chris Wilcox  and Greg Stiemsma  to free agent contracts and traded for Keyon Dooling . Daniels was a bust last season, Wilcox was sidelined after a promising start due to a heart issue, and Stiemsma was a high-energy shot-blocker in limited minutes. Dooling was a reserve guard who retired at the end of the season.
Ainge also acquired Brandon Bass  in a trade with Orlando for Glen Davis . The trade has worked for both sides. Bass is a starter in the frontcourt alongside Garnett. Davis is averaging 15.9 points and 8.4 rebounds for a struggling Magic team. Ainge also signed Mickael Pietrus  to serve the James Posey role, although Pietrus never fully grasped the expectations of Ainge and Rivers.
The Celtics eventually lost to the Heat in the Eastern Conference finals.
The verdict: Ainge still didn’t do enough to complement the Big Three and his new best player, Rondo. His mission before the 2012-13 season was to add depth and scoring.
2012-13 season: Ainge had his most active draft in the new Big Three era, selecting Jared Sullinger, Fab Melo and Kris Joseph. Sullinger is the only one who has made a contribution this season, and the Ohio State product looks as if he could be a role player for years to come. Melo and Joseph are projects, and the odds are stacked against them in terms of making an impact while guys like Garnett and Pierce are still manning the floor. Ainge also re-signed Garnett, in a demonstration of his ability to maintain his biggest assets. Likewise, he also resigned Bass, who has continued to improve playing alongside Garnett, Pierce and Rondo. Ainge replaced Ray Allen with Jason Terry  — a move that can’t be judged until the conclusion of this season. It appears as if Ainge could have signed both Allen and Terry if he made a harder push for Allen, but there is a question as to whether bringing back Allen would have been good for Rondo’s growth as a player and leader. Time will tell on that. There aren’t many early signs that Rondo is eager to take on more of a leadership role in the absence of Allen.
Ainge also traded for Courtney Lee , who should be a solid fourth guard in the rotation once Avery Bradley returns. Ainge retained Wilcox and signed Leandro Barbosa . Both players could fill roles late in the season. The biggest question mark in Ainge’s offseason is the four-year, $32 million contract he gave Jeff Green. After not playing basketball at all last season, Green is now the Celtics’ fourth-highest-paid player behind Pierce, Garnett and Rondo. Yet, on Wednesday night against Minnesota, when Green found himself in the fortunate position of being matched up against 5-foot-8 J.J. Barea on the offensive end, the well-paid Celtic struggled. The 6-foot-9 forward gathered the ball, recognized he was being guard by a player a foot smaller than him, put down a few dribbles, and tried to spin toward the basket by running through the smaller guard. Barea flopped and received the call for an offensive foul. Green could only salute Barea for outsmarting him, prompting Rivers to make a substitution for Green. You could almost see Rivers explain to Green that when he has a similar mismatch, there are two options: Shoot over the smaller player, or back him down to the basket until Green has a layup. As Rivers struggled to get through to Ainge’s biggest blind spot, all anyone could wonder is, “Is Danny Ainge getting in Doc’s way?”