Ranking the Ainge trades: The best of the best (No. 5-1)

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Danny Ainge has made 60 trades since being hired as the president of basketball operations for the Celtics in May 2003. With no basketball on the horizon until July, BSJ contributor Ryan Bernardoni and I teamed up for an enjoyable, albeit challenging endeavor: Ranking the Ainge trades from worst to best overall.

To accomplish this task, Ryan created a formula that allowed us to grade the deal based on a variety of factors (importance, quality) while also evaluating the deal at the time a trade was made and in hindsight (years later). Some deals will get the benefit of hindsight more than others in this exercise but we did our best to account for those issues. The end result is the following ranking from 60-1 with an analysis/explanation of each deal. 

You can check out the previous sections of the countdown here

Misfires (60-51)
Forgettable deals (50-29)
Debating the Perk trade (No. 28)
Above-average deals (27-16)
Smart business (15-11)
Game-changers (10-6)

Today, we close out the countdown with our top-5 deals.

5. Marcus Thornton and a 2016 Cavs first-round pick (No. 28 Skal Labisseire) to the Suns for Isaiah Thomas (February 2015)

The calculus was fairly easy for Boston here. Thornton was a pricey expiring contract who had no future in green so he was simply used here to match the money. The Celtics already had at least two other first-round picks for both the 2015 and 2016 drafts and there wasn’t going to be enough room on the depth chart to keep all those picks. In targeting Thomas, they found a Suns team with a distressed asset, primarily thanks to a roster structure that featured three high usage point guards that weren’t happy with reduced touches. In Boston, there was a clear need for a top scorer or two following the departures of Rondo and Green, making Thomas a nice fit for what the team thought at the time would be a sixth man scoring option. With Thomas having three years left on the deal at the time of the trade for mid-level money, this was dealing one future asset for another as the cost control involved with Isaiah’s deal (far below market value) would allow the team the ability to let him produce and turn himself into a greater asset that could be flipped again down the line. Having the chance to land a potential 20-point per game scorer for merely taking on a salary dump in the summer (taking on Thornton and Zeller gave them the Cavs' first-round pick used in the deal), was about as good as it gets when it comes to leveraging assets.

The impact of the Thomas move is layered in both the short and long term for Boston. In the interim, the 5-foot-9 guard served as a catalyst to a surprise trip to the postseason for the Celtics in 2014-15 as Boston closed out the year with a 20-10 stretch upon his arrival. That type of progress paved the way for the Celtics to return to a playoff team in the Eastern Conference ahead of schedule during Danny Ainge’s post-Big-3 rebuild. The domino effect of Thomas allowed the C’s to appeal to the likes of Al Horford and Gordon Hayward in free agency under Brad Stevens' watch. Thomas may have had a brief stay in Boston but getting a guy who turned into a top-5 MVP candidate for one season for a late first-round pick is a huge development.

The Thomas trade also set the stage for other players' values to be improved with a true No. 1 scoring option in play for Boston. While Thomas saw his value diminish due to injuries by the time he was dealt in a blockbuster deal for Kyrie Irving, he allowed several of his teammates to put together the best seasons of their career while feasting on the open shots he created for them. That came in handy for Boston with the likes of Jae Crowder and Avery Bradley helping to secure meaningful returns in trades for Irving and Marcus Morris respectively, which came in large part due to them being able to play secondary roles they thrived in.

While Thomas himself was probably the least appealing part of the Kyrie Irving trade from Cleveland’s perspective, the hope that he could rebound from a hip injury back in 2017 was enough for Boston to help outbid the pack for Irving when combined with Crowder and an unprotected pick from Brooklyn.

4. A protected 2007 first round pick (No. 24 Rudy Fernandez) and cash for the draft rights to Rajon Rondo (No. 21) and Brian Grant (June 2006)

Draft night in 2006 was a busy evening for Ainge and company. They kicked off the festivities with one blockbuster deal that saw them give up the No. 7 overall pick in order to land a young point guard prospect in Sebastian Telfair and rid themselves of a lengthy bad contract (Raef LaFrentz) for an easier one to deal (Theo Ratliff). One of the players the Celtics were considering taking if they held onto that No. 7 overall pick, according to a team source, was Kentucky sophomore Rajon Rondo. So when the prospect found himself free falling toward the bottom half of the first round, Ainge, (with a strong push from former assistant GM Ryan McDonough) made a pitch to ownership: Help me buy my way back into the first round to add another elite rookie.

Wyc Grousbeck and the rest of Celtics ownership delivered on that front. They authorized Ainge to send a few million dollars the Suns' way and absorbed a bad contract (Brian Grant, who retired before the season began) in order to land the No. 21 pick and nab Rondo. Landing a key asset like this (given how poorly Telfair fared in Boston) was essential for the Celtics’ transformation into a contender two years later. Ainge had been stockpiling assets for trades but there’s a real chance the guard cupboard would have been bare in Boston in 2007 as far as a young supporting cast goes if Rondo weren’t selected here. Delonte West and Telfair were shipped off as part of trade packages for Ray Allen and Telfair respectively. Tony Allen was not a point guard, leaving a likely mix of Eddie House, Sam Cassell and free-agent veteran X manning the point guard spot all year long for the 2007-08 squad. Would that have been enough to win a championship in 2008? It’s possible but certainly not probable. However, there’s no doubt that Rondo’s emergence as an All-Star gave the Big Three era a couple extra years of shelf life as age and injuries wore down Garnett, Pierce and Allen.

The draft night acquisition was the beginning of a largely perfect track record that Ainge had with managing Rondo’s value as a player. He fought hard to keep him out of deals for Ray Allen and Garnett after a promising rookie season. He signed him to what ended up being a very team-friendly extension (five years, $55 million) at the beginning of a breakout 2009-10 campaign. Finally, he ended up selling on the point guard after two strong months in the beginning of the 2013-14 season before his value ended up cratering following a tumultuous half-season in Dallas. That type of timing has made Ainge one of the longest-tenured general managers in the league.

3. Kevin Garnett, Paul Pierce, Jason Terry, DJ White and a 2017 second round pick (No. 57 Aleksandar Vezenkov) to the Nets for Gerald Wallace, Kris Humphries, MarShon Brooks, Keith Bogans, a 2014 first round pick (No. 17 James Young), a 2016 first round pick (No. 3 Jaylen Brown), a 2017 pick swap option (No. 1 Markelle Fultz for No. 27 Kyle Kuzma) and a 2018 first round pick (No. 8 Colin Sexton) (June 2013)

There’s a very good chance that this trade will be No. 1 on this list in another 5-10 years. For now, championships take precedence, and this blockbuster hasn’t produced any for the franchise just yet. With two All-Star caliber players still in green as a direct result of this deal, it may only be a matter of time before the development of Jayson Tatum and Jaylen Brown pushes this higher up the list.

For now, it’s just incredible how much the Celtics managed to squeeze out of the Nets in this deal, a trade that looked like an ordinary return on draft night in 2013. Brooklyn was building a high-priced contender, but their ownership lacked the financial commitment to see it out and keep paying the luxury tax. That, combined with a core that started falling apart as soon as 2015 (Deron Williams fell off a cliff), quickly turned the Nets from a solid playoff team to a cellar dweller with no path to improvement by the time 2016 rolled around.

The results of this deal for Boston should have been even better if it weren’t for some bad luck. James Young was a complete miss at No. 17 in the 2014 NBA Draft and giving up the 2018 Nets pick for Kyrie Irving ended up being a big mistake in hindsight after Irving’s flip-flop on staying. Despite those blemishes, this could be one of the greatest hauls for Ainge in Celtics history when all is said and done given the current trajectories of Brown and Tatum. With both players set to be locked up throughout their primes in Boston, this trade has ensured the Celtics should remain in the contending conversation for much of the next decade, assuming the right supplemental pieces are put around them.

Ainge was prepared to let Garnett and Pierce finish off their careers in Boston, that is until he found a team in Brooklyn willing to pay sticker price for both with draft capital. Ainge’s willingness to absorb salaries/bad contracts (Gerald Wallace/Keith Bogans) in order to maximize future assets could end up making this deal one of the biggest steals in NBA history when all is said and done.

2. Wally Szczerbiak, Delonte West, the draft rights to Jeff Green (2007 -- No. 5) and a 2008 second round pick (No. 49 Trent Plaisted) to the Supersonics for Ray Allen and the No. 35 overall pick (Glen Davis) (June 2007)

Ryan Bernardoni: A challenge in this activity has been deciding how to rank the pieces of trade chains. The acquisition of Isaiah Thomas is fifth, but the move that is viewed as having set it up is tenth. Should the source trade always be ranked higher than what it made possible?

In the case of the Thomas chain, the answer is obviously “no” because Marcus Thornton and a late first-round pick are not irreplaceable assets. If Boston didn’t have them there would have been other ways to put together an acceptable package.

In the case of the acquisition of Kevin Garnett, things get murky. Acquiring the T-Wolves future pick in the Ricky Davis trade and Theo Ratliff’s expiring deal were possibly critical progenitors and we weighed that into their rankings, but neither were ever in serious consideration for the top spot. The link is still too tenuous.

The trade for Ray Allen, on the other hand, does have a case for number one partly based on this thinking. Before the trade, Garnett did not want to come to Boston. After it, he signed off on being traded and even agreed to an extension. It appears to be a direct line where one would not have happened without the other.

It’s also just a fantastic trade on its own. The SuperSonics were picking Kevin Durant, tanking, and getting ready to move to Oklahoma City. They wanted to be young and bad and that gave the Celtics the opportunity they needed.

The fifth pick is a good asset, but one year prior Ainge gave up the seventh pick just to shuffle contracts around. Szczerbiak was a nice player but his time as an above-average starter was in the rearview mirror. Delonte West was a good role player but also an established commodity at that level.

Allen was a seven-time All-Star and already future Hall of Famer who was also a seamless fit next to Paul Pierce and the key to unlocking the Garnett trade. Yes he was 31 years old, but also known to be one of the most fit players in the league. To get him without giving up Al Jefferson, Kendrick Perkins, the future Minnesota pick, or Rajon Rondo, while also getting Glen Davis thrown in, was masterful business.

The Garnett trade was always going to sit at the top of these rankings, and we both had it here in our individual scoring. However, if you’re ever going to give full credit for what a trade ultimately made possible, this move has a strong claim to being Ainge’s best.

1. Al Jefferson, Gerald Green, Theo Ratliff, Ryan Gomes, Sebastian Telfair, Minnesota’s 2009 first round pick (No. 6 Jonny Flynn) and a Celtics 2009 first round pick (No. 28 Wayne Ellington) to the Timberwolves for Kevin Garnett (July 2007)