Breaking down Danny Ainge's five biggest mistakes of the "Big Three" era

As crazy as it may seem, Danny Ainge just completed his 10th season running the Celtics. He took over the team as they were getting swept in the 2003 playoffs by the Nets, and immediately made his mark that summer, trading all-star Antoine Walker for banged up big man Raef LaFrentz. Not exactly starting off with a bang.

The next four years were bizarre. Slowly but surely Ainge changed the roster, through both trades (CSNNE's Rich Levine has a great break down of Ainge's early deals) and shrewd drafting (Ainge crushed the draft from '03-'06 picking up Perk, Al Jefferson, Tony Allen, Delonte West, Rondo and Leon Powe). The roster makeover left the Celtics as a terrible team finishing up the 2006-07 season, but Ainge had acquired a ton of assets. Once the ping-pong balls once again refused to go the Celtics way in the '07 draft lottery, Ainge cashed in on the assets he acquired.

Jefferson, West, Gerald Green, Sebastian Telfair, Ryan Gomes, the #5 pick in the '07 draft (Jeff Green), a future 1st round pick and Theo Ratliff's expiring contract were out.

Kevin Garnett, Ray Allen and Glen Davis were in.

And just like that, a new era of Celtics basketball was born.

Over the past six seasons, Ainge has stewarded the C's to six consecutive playoff appearances, five trips to the second round, three Conference finals appearances, two Finals berths and the 2008 championship. A fantastic run of success that is just now winding down ( be continued on that).

Ainge has made a ton of good decisions over the past six years to help fortify the roster; from signing James Posey in 2007, to bringing in P.J. Brown off the street later that same season, to drafting Avery Bradley (2010), and Jared Sullinger (2012), and re-signing Paul Pierce to an extremely team friendly 4 year, $60 million deal in 2010, Ainge has hit more than he has missed.

But still, he has missed. From 2003-07 Ainge's mistakes were plentiful (drafting Gerald Green in 2005, the aforementioned Lafrentz deal, the Sebastian Telfair experience, ect), but at the end of the day Ainge acquired enough assets to make his next move. Wrong decisions or not, he ended up cashing in his chips and helped give birth to the next great era of Celtics basketball.

However you can't say the same thing about Ainge's mistakes since 2007. Every misfire from the C's boss since the assembling of the big three has stung as the C's have fallen short in three Game 7's since 2009, including two extremely close series losses to eventual champs (2010 Lakers, 2012 Heat). What mistakes am I talking about? Let's take a look back at Ainge's biggest mistakes since 2007, keeping in mind that hindsight is always 20/20.

5. Overpaying role players during the Summer of 2012
$17 million for Lee (pictured), Bass and Terry is a massive overpay

Facts: Ainge signed 27 year old Brandon Bass (12.5 PPG, 6.2 RPG in 2011-12) to a 3 year, $19.5 million deal, 35 year old Jason Terry (15.1 PPG in 2011-12) to a 3 year, $15.7 million deal and traded for and then signed 27 year old Courtney Lee (11.4 PPG in 2011-12) to a 4 year, $21.25 million deal.

At the time, everyone applauded Ainge for his 2012 off-season, and seemingly for good reason. He had just taken an Eastern Conference finals squad and completely upgraded a terrible bench (led by Mickael Pietrus and Keyon Dooling), bringing in Terry and Lee, plus re-signing Bass who had been solid as a starter for Boston. If Boston was going to reload around Pierce and KG, the team would need role players to surround them and complement their skill-sets.

However it didn't work out. Bass regressed to Orlando form while Terry looked every bit of his 35 years old and Lee lost his rotation spot come playoff time. The C's spent $17 million on the trio and got basically replacement level value this season, and even worse, they will clog an additional $17 million worth of payroll in 2013-14, and $18 million more in 2014-15. The mistake didn't just hurt Boston this season, but seems likely to haunt them the next few years as other teams aren't exactly lining up to pay average players real coin money. As Boston looks to either rebuild or reload, there is little doubt last summer will haunt Ainge for a few years.

4. Letting James Posey go/not adequately replacing him in 2008
Greatest Celtics bench player of this generation

Facts: The Celtics offered Posey a 3 year, ~$17.5 million deal following the 2008 title run, but would not add a 4th year. Posey ended up signing a 4 year, $25 million deal with the New Orleans Hornets.

James Posey, the greatest bench player in (recent) Celtics history. Man did this guy fit the C's like a glove. The numbers say Posey averaged 7.4 points and 4.4 rebounds a game for the Celts in 2007-08, but in this case the numbers don't tell the story. Posey was an elite wing defender that knocked down 38% of his threes, playing the role of 6th man as the Celtics won their first title since 1986.

Flash forward to the summer, and Boston refused to add a 4th year to Posey's deal, maxing out with a 3 year deal for the full mid-level exception. New Orleans, coming off a surprise trip to the Western Conference semi-finals, swooped in and gave Posey that highly valued 4th year, and just like that, he was gone.

In retrospect, this move hurt both teams. Posey was good for all of one season in New Orleans, was dumped after year two, and out of the league after year three. If New Orleans could do it all over again, they would never have called Posey's agent.

However it also killed Boston. The C's never came close to replacing Posey and his 'D and 3' mentality, and the end result was Paul Pierce spending many a crunch time guarding players like LeBron James and sapping him of his offensive energy. It's entirely possible that Posey would have faded early in Boston as well, but for the 2009 and 2010 seasons there is little doubt that his absence killed Boston's title chances.

3. Rasheed Wallace, Jermaine O'Neal and the big man carousel
How I felt watching Sheed during his one year in green

Facts: Boston signed Wallace to a 3 year, $18 million deal in the summer of 2009, and following Wallace's retirement after the 2010 season, signed O'Neal to a 2 year, $12 million pact.

Fool me once, shame on you, fool me twice, shame on me. For some reason Ainge has been completely ineffective at bringing in big men since luring P.J. Brown out of retirement for the '08 stretch run. Some of the deals have been for small money (Shaq at $2 million per year), and are easy to sweep under the rug. Others, namely Sheed and Jermaine O'Neal, have been disappointments on the court while sucking up a big chunk of the salary cap.

Many Celtics fans seem to look back at Wallace's Celtics tenure and remember only his gutty Game 7 performance in the 2010 Finals (11 points and 6 rebounds). However it's important to note that Sheed was given over $6 million per season, showed up woefully out of shape, and was extremely inconsistent throughout the Celts playoff run (6.1 PPG, 3 RPG in 17 MPG). Following the heartbreaking loss, the Green were thrown a bone; Sheed was retiring, and most of his $6 million cap hit was going with him. Now what to spend the money on? How about..

O'Neal. Ugh. Unlike Wallace, no Celtics fan has a single fond memory of 'The Jermaine era', a two year run of missed games (119 including playoffs), lethargic play (5.2 PPG and 4.6 RPG) and wasted money. Obviously we're working with three years worth of hindsight, but Boston would have been better suited going for a slew of big men available for less money (Kris Humphries, Al Harrington, Ian Mahinmi) or allocating the resources elsewhere (Matt Barnes, Kyle Korver both available at reasonable prices). Or they could have taken a chunk of the money offered to O'Neal, and offered it to this guy.

2. Letting Tony Allen go after the 2010 season
Tony Allen's defense has been badly missed

Facts: Following the 2010 Finals, Tony Allen was offered a 2 year deal worth approximately $6 million by Boston, but instead signed a 3 year, $9.5 million deal with the Memphis Grizzlies.

Tony Allen, we hardly knew ye. For a brief span in the ill-fated 2006-07 season, Tony Allen was playing like All-Star. During a 14 game span in December and January, Allen averaged 18.9 points, 5.9 rebounds, 2.9 assists and 2.6 steals while shooting 54% from the field and 80% from the line. And then this happened. A blown out knee on a post whistle dunk, and T.A.'s time in the sun was over before it really even started.

That summer the C's traded for Ray Allen and signed Posey, and T.A. was basically forgotten about as he rehabbed his injury. Over the next three years Allen's playing time was inconsistent, but he played fantastic against LeBron James in the 2010 Eastern Conference semi's. Allen averaged 8 points per game in 20 minutes, but far more importantly helped hold LBJ to just 44.7% shooting and forced him into 4.5 turnovers per game as the C's upset the Cavs.

That summer when it came down to free agency, Allen wanted a 3 year deal, but Ainge balked and instead offered a two year pact. Once Memphis offered a 3rd year, Allen bolted without even coming back to Boston for a counter, and the rest is history. Allen has made three All-Defensive teams in three years with the Grizzlies, and has held a starting role on a team that has made three straight playoff appearances, punctuated by a run to the Western Conference finals this year. His $3 million annual salary is undoubtedly one of the best values in basketball, and his defensive presence has been badly missed in Boston.

In each of the past three seasons Boston has been eliminated by teams with an elite wing scorer (LeBron in 2011/2012, Melo in 2013), and you have to wonder how much of a difference Allen would have made.

1. Drafting J.R. Giddens over Nikola Pekovic, Mario Chalmers and DeAndre Jordan in 2008
Hey TB, what the hell happened to J.R. Giddens?

Facts: With the 30th pick in the 2008 Draft, Ainge selected New Mexico guard J.R. Giddens, who would play 35 NBA games in his career. Pekovic, Chalmers, Jordan, Omer Asik and Luc Mbah a Moute would all be drafted in the next seven picks.

It's rare that a draft produces so many early second round values, but the 2008 draft did just that. Three legitimate starting centers in Pekovic, Jordan and Asik, a sweet shooting combo guard in Chalmers and a fantastic wing defender in Mbah a Moute all went between picks 31-37.

Considering the C's held the 30th pick, and were looking for players to add to their championship core, Chalmers and Jordan made the most sense. However Ainge decided to roll the dice with Giddens, and it ended up hurting big time. One of the marks of great franchises is their ability to find talent in the late first and second rounds of the draft, a spot where the San Antonio Spurs have found countless quality players, including two future Hall of Famers in Tony Parker and Manu Ginobili.

In '08, Ainge had a plethora of talent at his disposal, but couldn't get the job done. The failings in this draft ended up leading to other mistakes on this list as well, as Jordan could have blocked the signings of Wallace and O'Neal and freed up that money elsewhere, and Chalmers could have helped slow the carousel of backup point guards to roll through Boston over the past five seasons.

Instead the C's got nothing from the draft, just like they got nothing from the 2009 draft (no 1st round pick) and the 2011 draft (JuJuan Johnson over Jimmy Butler, ouch). In Ainge's defense, his overall draft record is fantastic. Without the use of a single top 10 pick, he has scooped up Perkins, Jefferson, West, Allen, Rondo, Powe, Glen Davis, Bradley and Sullinger, certainly a resume that any GM could be proud of.

However his swing in miss in 2008 really hurt a championship team that needed immediate help, and instead got Giddens and his 8 career points with the Celtics.

So there are my 'Five moves to forget', be sure to leave yours in the comments.

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