Ranking the Ainge trades: The good deals (27-16) – From Gary Payton and Rick Fox to Rajon Rondo

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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 for at least the next two months, 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. 

We looked at part one of the series on Wednesday and some forgettable ones on Thursday, and debated the Perk trade on Monday. For Part 4, we begin to break down Ainge's good deals, of which there are many. 

27. Gary Payton, Tom Gugliotta, Michael Stewart and a 2o06 first-round pick (No. 21 Rajon Rondo) to the Hawks for Antoine Walker (February 2005)

This was an admirable attempt at a playoff run (and nostalgia) for the 2005 playoff run in a weak Eastern Conference. There was no player cost for this trade as Payton was immediately waived by Atlanta and re-signed with Boston after the deal was done. Gugliotta and Stewart were only inserted for salary purposes making the true price here being the Rondo pick. However, after an unsuccessful playoff run (Walker played solid in a seven-game loss to the Pacers in the first round), Ainge turned around and nabbed two high second-round picks for him during a sign-and-trade, recouping most of the value of the first-round pick.

26. Chucky Atkins, Chris Mihm and Jumaine Jones to the Lakers for Gary Payton, Rick Fox, a 2006 first-round pick and cash (August 2004)

This was a rare amended deal for both sides after Gary Payton refused to report to Boston for a physical in the middle of August. In response, the Celtics were able to send the Lakers Jumaine Jones instead of Marcus Banks, and Boston kept an extra second-round pick as well. Both of those shifts put this in the positive deal column.

The principles for this deal were simple. The Lakers wanted to get rid of some pricy veteran talent (Fox, Payton), and the Celtics were willing to give up some unremarkable middle-of-the-road talent for some old guys and a first-round pick for their troubles. Payton actually had a solid season in his one year in Green while Fox retired before training camp. Kobe Bryant wasn’t able to turn a bunch of role players (including all three players acquired in this deal) into a playoff team, so consider this one a win for the C’s by landing a first-round pick that ultimately became Rajon Rondo.

25. The draft rights to Albert Miralles to the Bucks for Keyon Dooling and a protected second-round pick (December 2011)

Getting something for nothing is never a bad idea, and Ainge took advantage here. The Bucks were looking to dump the 30-year old Dooling who was making a reasonable $2.2 million in the final year of his deal. The Celtics were in the market for a backup point guard and bounced after the lockout ended. Dooling’s regular season was rather underwhelming (career-low 4.0 ppg), but he was a key bench contributor in the postseason (39.3% from 3-point range) to help the C’s battle to Game 7 of the Eastern Conference Finals.

24. The 2016 No. 16 pick (Bebe Nogueira) and two 2014 second-round picks (Cleanthony Early, Russ Smith) to the Mavs for the No. 13 overall pick (Kelly Olynyk) (June 2013)

In hindsight, a lot of the attention in this draft is on the Celtics (and 13 other teams) passing on Giannis Antetokounmpo in the first round, but Olynyk has ended up becoming a top-10 player in this 2013 draft class. Ainge paid a fair price (two second-round picks) to move up the three spots and nab Olynyk, and the seven-footer helped the C’s in the rebuilding process during his four years in Green as an outside shooting threat and skilled big. Olynyk eventually walked for nothing (the C’s used his cap room on Gordon Hayward instead). Nogueira played one useful season in the NBA (in Toronto) but hasn’t played in the NBA since 2018.

23. Keith Bogans and two protected second-round picks (did not convey) to the Cavs for Dwight Powell, Erik Murphy, Malcolm Thomas, John Lucas, 2016 second-round pick (58. Abdel Nader) and 2017 second-round pick (53. Kadeem Allen) (September 2014)

Perhaps the biggest collection of meaningless players in an Ainge deal during this era. The calculus behind this one was quite simple. Bogans was acquired and given a hefty salary (with non-guaranteed money attached) to help make the KG/Pierce trade with the Nets work under salary rules. Boston sent Bogans home two months into his first season in Green when he was making a stink about a lack of playing time, not realizing that the C’s had only acquired him to make the deal work and perhaps use him in a trade later.

Decision time came a year later when Bogans’ $5 million unguaranteed salary was shopped around to teams as a potential trade asset for the upcoming year. Eventually, the C’s landed on a fairly underwhelming return: a Cavs team that was looking for some salary relief. The Celtics took on four cheap Cavs contracts, keeping only recent draft pick Dwight Powell. They also added two future second-round selections for their trouble that eventually turned into a couple of decent players in Nader and Allen for those slots in the draft.

In the big picture, this deal meant very little but is yet another example of Ainge leveraging one part of a deal (taking on Bogans) and turning it into a positive asset on the tail end.

22. Chris Mills to the Hawks and Mike James to the Pistons for Linsdey Hunter, Chucky Atkins, a 2004 first-round pick (No. 25 Tony Allen), and cash (February 2004)

Ryan Bernardoni: One theme that comes up multiple times in this list is that Ainge understands trade leverage better than most. We covered earlier how he moved early to clear Aron Baynes’s salary for a relatively low price before competitors knew he had to do it to complete the Kemba Walker signing. Other franchises have been caught out in similar situations and had to give up multiple picks to dump useful players because they were slower to react.

This is the first of two trades where he played on the other side of that equation and instead of waiting to squeeze every asset he could imagine from a team that needs to dump salary, he moved quickly to ensure that he got something before a different team could make a better offer. It’s better to get one free pick than to dream of two while getting none.

In this case, Ainge angered much of the league for helping Detroit acquire Rasheed Wallace and go on to win the title. The Celtics weren’t in a position to care who exactly took home the prize that year; it obviously wasn’t going to be them. Of course, the reality is that if Ainge hadn’t agreed to facilitate someone else would have. The bounty the Celtics were able to collect was the pick that became Tony Allen, a nice return under the circumstances.

21. Brandan Wright to the Suns for two second-round picks (No. 35 Rade Zagorac, No. 37 Semi Ojeleye) (January 2015)

Officially, this was a protected Minnesota first-round pick when the deal was made but the Wolves had no realistic shot of making the playoffs at that point, making the end game two second-round picks.

Wright was probably at the peak of his NBA powers at the time of this deal as a rim running big man. However, he had no fit in Brad Stevens’ offense during his eight games in Boston after being acquired in the Rajon Rondo deal. Instead, Ainge cashed in on Wright’s expiring contract for future picks and cleaned out some of the frontcourt glut he had created. The Celtics eventually managed to land a future first-round pick thanks to packaging one of the high second round picks (No. 35) in this deal with another high second pick (No. 31) back in 2016. They also landed defensive specialist Semi Ojeleye in 2017 with the other second-rounder. Wright went on to sign a three-year deal for mid-level money with Memphis in the summer of 2015 but only played 67 games over the next three seasons due to injury issues.

20. Eddie House, Henry Walker, J.R. Giddens and a protected second-round pick (did not convey) to the Knicks for Nate Robinson and Marcus Landry (February 2010)

Any deal that brings you closer to a championship in-season is worthy of heavy praise, and that’s what Ainge did here. The Celtics bench was lacking firepower in 2010 as Eddie House was looking slower than ever on the defensive end and failing to make 3s as much as the last two seasons. Meanwhile, a disgruntled Nate Robinson was constantly butting heads with Mike D’Antoni on a miserable Knicks team and looking for an exit strategy.

Ainge really didn’t have any meaningful assets that he wanted to trade on the roster but managed to put together a pu pu platter here for Robinson. Henry Walker probably had the most value out of this Celtics trio while J.R. Giddens had been a disappointment since the C’s wasted a pick on him in 2008. Walker ended up having some staying power in New York for a few seasons before falling out of the league while Giddens was out of the NBA by the end of this season.

Meanwhile, the Celtics received a bench spark plug in Robinson who was still in his prime. He outplayed House during the remainder of the regular season but found himself out of the playoff rotation due to matchups and his defensive/size limitations. However, Robinson delivered clutch performances in a series-clinching Game 6 against the Magic (13 points in 13 minutes) and during Game 4 of the NBA Finals during the ‘Donkey and Shrek’ win over the Lakers. There is still some valid second-guessing to this day about the lack of playing time for Robinson in Game 7 against the Lakers (3 minutes played) for an offensively challenged and gassed Celtics team.

Ainge should have re-signed Tony Allen instead of Robinson after this Finals run, but the trade pickup for essentially nothing useful here was an important win.

19. Rajon Rondo and Dwight Powell for Brandan Wright, Jameer Nelson, Jae Crowder, a protected 2015 first-round pick (2016 No. 16 Guerschon Yabusele), a 2016 second-round pick (No. 45 Demetrius Jackson), and the creation of a $12.9M trade exception (December 2014)