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

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)

Ryan Bernardoni: If you did a poll of the basketball world when this trade went down and asked for a ranking of the assets in it, it probably would have looked something like this:

1.     Rajon Rondo
2.     Future first-round pick
3.     Brandan Wright
4.     $12.9M TPE
5.     Jameer Nelson
6.     Future second-round pick
7.     Dwight Powell
8.     Jae Crowder

A lifetime later and things look very different. Rondo flamed out of Dallas in spectacular fashion and has been a below-average journeyman ever since. The first-round pick became Guerschon Yabusele who brought joy but little else and will sit on the C’s cap sheet for two more years.

Wright was flipped for two second-round picks and hasn’t been healthy since. The picks he was traded for were somewhat more valuable. One became Semi Ojeleye and the other is part of the trail that leads to Carsen Edwards and the Bucks’ 2020 first-round pick.

The trade exception was renounced in the summer of Amir Johnson. Jameer Nelson was unhappy in Boston and quickly moved on for Nate Robinson who was immediately waived. The 2nd round pick became Demetrius Jackson who played 17 glorious minutes for the Celtics before being waived and is currently in the G-League.

The only two pieces in the trade that provided positive value more than a month beyond its conception were Powell and Crowder, and the 1st round pick as a theoretical entity before being used.

Crowder quickly won a rotation spot in Boston, signed a long, team-friendly deal as a restricted free agent, and went on to play over 200 games in green before becoming part of the ill-fated Kyrie Irving trade. He was an unequivocally positive piece of the trade, even if he was probably only included to make the trade math work (thankfully Ainge asked for him instead of Ricky Ledo or Phil Pressey).

18. A 2007 second-round pick (No. 49 Aaron Gray) to the Nuggets for a 2006 second-round pick (No. 49 Leon Powe) (June 2006):

Powe was one of the most beloved role players from the Big Three era despite only playing three seasons in Boston. An untimely ACL tear in 2009 ruined his postseason and decimated the C’s frontcourt depth in conjunction with Kevin Garnett’s knee injury. Ainge wisely bet he was done by that point, declining to re-sign him that offseason, a move that miffed fans but was ultimately the right call.

Before that? Powe was found money as a second-round pick that provided productive minutes almost immediately after his rookie season. Injury woes caused his stock to drop for the draft, but Ainge took advantage by trading a future pick for the power forward, giving the C’s an elite offensive rebounder and big man capable of drawing fouls constantly in the post. Powe ranked second in win shares per 48 minutes on both the 2008 and 2009 teams despite his limited role off the bench. Injuries ended his career too soon, but he will always have his dominant Game 1 effort against the Lakers in the 2008 NBA Finals that will earn him praise from Celtics fans until the end of time.

17. Glen Davis and Von Wafer to the Magic for Brandon Bass (December 2011, sign-and-trade). Weight issues and inconsistent play caused the Celtics to run out of patience with Big Baby by the time he hit free agency in 2011. With no meaningful cap space to replace him with, the C’s still couldn’t afford to lose him without compensation but they weren’t looking to pay up anyway. The solution? Finding a better replacement at his position in the form of underutilized Magic power forward Brandon Bass.

The end result was a sign-and-trade just as the NBA lockout ended in 2011, and Davis was shipped to Orlando with a three-year deal along with reserve guard Von Wafer. In return, the C’s got the versatile Bass who played a key scoring and defensive role for the team on the way to Game 7 of the NBA East Finals starting alongside Kevin Garnett in the frontcourt. Bass was a midrange pick-and-pop master and a great offensive rebounder for his size. Ainge nabbing him for a guy he didn’t want to pay anyway was a stealthy move that helped extend the end of the Big Three era.

16. Tayshaun Prince to the Pistons for Jonas Jerebko and Gigi Datome (February 2015)
Prince was a Brad Stevens favorite during his one month with the C’s (the head coach still brings him up to this day once in a while), but he was over the hill at this point in his career after arriving as salary filler in the Jeff Green trade. Stan Van Gundy was looking for some veteran leadership in Detroit however and gave up a couple younger prospects for the C’s to get a free look at. Datome only lasted two months in Boston before heading back to Europe for a standout career. Jerebko however turned into a useful stretch 4 for the next 2.5 years in Boston, which helped to lift Boston from a rebuilding team to a top-3 squad in the Eastern Conference.