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Ranking the Ainge Trades: The Misfires (60-51)

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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 them 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 will unveil roughly 10 of these trades every day for the next week, counting down to the top. We’ll also fight about a couple in which we have substantially different evaluations of how Ainge fared with them.

The vast majority of these deals produced positive results for ‘Trader Danny’ over his 17 years at the helm in Boston but there were a few rough patches for the executive. As such we begin our list from the bottom, with one of the most recent deals during Ainge’s tenure:

60. Jae Crowder, Isaiah Thomas, Ante Zizic, 2018 unprotected Nets first-round pick (No. 8 - Colin Sexton), and two future second-round picks for Kyrie Irving (August 2017)

It’s easy to pan this trade now after the Irving era ended in Boston with the All-Star walking out the door with no return for Boston. However, even at the time, this was a hefty price that Ainge paid given Irving’s circumstances with the Cavs. Irving had demanded a trade out of Cleveland and was threatening to hold out and have surgery on his knee if he didn’t get his wish. Irving also had a lengthy injury history and chemistry issues with LeBron James and the coaching staff in Cleveland. Whether or not he could be a No. 1 option on a contender was very much in question in 2017, something the C’s were asking of him when they made this deal.

The Celtics had a treasure chest of assets in the form of picks and good value contracts at this time, even with Isaiah Thomas having no real value in the summer of 2017 because of his hip injury. Acquiring Irving was part of a plan to eventually appeal to other big names to come to Boston (Anthony Davis, Kevin Durant, etc.). Ultimately, the Irving trade cost the C’s a realistic chance at numerous big names that became available in the preceding year on the trade market (Kawhi Leonard, Jimmy Butler, Anthony Davis in 2018 [due to Rose Rule]). While there is no guarantee those players would have stayed in Boston long-term, all of them would have raised Boston’s contending ceiling higher than Irving did during his two years in green.

For a more in-depth look at the sliding doors possibilities that would have been created if the Irving deal never happened, you can check out this column. For the purposes of this rankings exercise, it’s simple: Ainge bet big and lost. As Ryan points out, Ainge actually lucked out here with the Nets overachieving and handing the Cavs just the No. 8 overall pick. If that pick lands in the top-5 or if the Cavs got lucky in the lottery, the C's would have given up a chance at a young building block like Luka Doncic, Jaren Jackson or Trae Young.

59. Austin Rivers to the Clippers for a 2017 Clippers second-round pick (No. 57 Jabari Bird), Chris Douglas-Roberts and Shavlik Randolph in a three-team trade (January 2015)

Ainge had plenty of good trades during his 2014-15 in-season makeover of the Celtics roster. This was not one of them. Rivers arrived in Boston as part of the three-team Jeff Green deal with the Grizzlies and Pelicans. New Orleans sold low on the 22-year-old Rivers at the time after 2.5 underwhelming seasons in the Bayou. The real prize the Celtics got for Green was a protected first-round pick from Memphis (still pending in 2019) and Rivers was a secondary addition.

With all the success the Celtics had in rehabbing trade value of players during this era, keeping the former lottery pick Rivers aboard for a few weeks may have helped the C’s rebuild his value and gain more assets. Keeping him as a bench piece was a legitimate option as well due to his youth.

Instead, Ainge gave him away to his father essentially for a late second-round pick, a guy who was waived right away (Chris Douglas-Roberts) and a big man who only played five games that season (Shavlik Randolph). Meanwhile, Rivers turned into a useful bench piece for the Clippers for the next three seasons. His dad overpaid him a couple of years later but he ended up being both cheap and useful in LA off the bench before being rewarded by his dad with a bloated contract. Ainge sold low here in what could be categorized as a missed opportunity.

58. E’Twaun Moore, JaJuan Johnson, Sean Williams, Sasha Pavlovic and three 2013 second-round picks for Courtney Lee in a sign-and-trade with Houston and Portland (July 2012)

Following the departure of Ray Allen to Miami, the Celtics were desperate for some shooting and defensive help on the wing but had no way of bringing some aboard after using their full mid-level exception on Jason Terry earlier that summer. The alternative ended up being sacrificing several assets for the right to sign Lee (a restricted free agent in Houston) to a four-year, $21-million deal. Lee surprisingly underwhelmed during his one season playing under Doc Rivers, essentially falling out of the rotation entirely in the 2013 postseason. He was unceremoniously traded a year later to Memphis.

For 1.5 seasons of average play, the Celtics gave up Moore, who developed into a useful bench shooter for about 15 percent of Lee’s salary over the next few seasons in Orlando and Chicago before signing a big deal in New Orleans. That, combined with giving up three picks in the top-45 (No. 33, 39, 45), for a pricy bench role player was a poor gamble.

57. Gerald Wallace to the Warriors for David Lee (July 2015) 

The Celtics absorbed Wallace’s bad contract initially as part of the KG/Pierce blockbuster deal with the Nets. After serving as a veteran leader during his first year in Boston, Wallace turned into a $10 million bench cheerleader in year two as the C’s rebuild turned to its youth.

Ainge elected to dump Wallace’s expiring deal for another pricey, washed-up power forward in the summer of 2015 in David Lee. The 32-year-old had just lost his starting job to Draymond Green for the Warriors and was making a whopping $15.4 million in the final year of his deal.

His stay in Boston was a major disappointment as he posted career-worst production on the offensive end (45% FG) while blocking minutes for younger talent in the frontcourt. He was eventually benched in January and waived for nothing after the trade deadline, costing the C’s ownership millions for a guy who was over the hill.

56. Antoine Walker and Tony Delk to the Mavericks for Raef LaFrentz, Chris Mills, Jiri Welsch, and a 2004 1st Round Draft Pick (24th) (October 2003) 

I had this one pegged as one of Ainge's worst three trades while Ryan graded it as a net neutral move (he explains why below). From my standpoint, it's easy to see why Ainge decided to shake things after the Celtics were dominated by the Nets in his arrival. He was not a fan of Walker's game (something he noted as a TV analyst on multiple occasions) and the C's were going to develop into a contender with just him and Pierce leading the way. The problem? Ainge traded one bad deal in Walker for an even worse one in LaFrentz (six years, $65 million left). Taking on that was essentially turning one bad deal into another one and it certainly wasn't worth doing it for Jiri Welsch and a late first-round pick as the payoff.

Ryan Bernardoni: Ainge’s first major move as Boston’s GM was to trade Antoine Walker who, at 27 years old, had made three All-Star teams. Walker had two years left on his six-year, $71-million extension that was, at the time of signing, the richest in Celtics’ history. He was one of the two faces of the franchise.

The return was understood to primarily be Raef LaFrentz, a stretch-5 before those existed, who had never scored more than 15 PPG but had managed to secure one of the worst contracts in the NBA. At the time of the trade, it had six years and $65M still on it. He might have been a better player than the pre-analytics movement league realized, but not at that price.

It seemed like Ainge had flipped two seasons of an All-Star in his prime for six years of a solid role player who was being paid like an All-Star. For his trouble he also had to include Tony Delk, a productive spot-starter, and eat the final year of out-of-the-league Chris Mills’s expensive contract.

The pay-off for this was Jiri Welsch, who had shown less than nothing at that point in his young career but had been a mid-1st round pick, and one future, late 1st round pick.

In short, this was a terrible deal that should absolutely not have worked out.

The future pick became Delonte West. West became a part of the trade for Ray Allen and Glen Davis. Welsch was traded for a 1st that was traded for the pick that became Rajon Rondo. Even LaFrentz, by way of an expensive trade to move a year of his deal for the less bloated contract of Theo Ratliff, was a part of the Kevin Garnett puzzle.

This miserable trade that was probably just Ainge taking a heavy loss to move Walker and get himself a clean slate seeded the ground for the Garnett and Allen trades and the 2008 title. Something about it being better to be lucky than good…

55. Courtney Lee and a 2016 second-round pick to the Grizzlies for Jerryd Bayless and Ryan Gomes (December 2013) 

This was largely a long contract dump for the rebuilding Celtics in the first year of the Brad Stevens era. Lee was actually playing well, but an overstocked backcourt left him playing limited minutes per game. At age 28, he wasn’t a part of the future, so the C’s elected to dump his years with a pick for a look at Jerryd Bayless on an expiring deal.

This was a rare miscalculation on Ainge’s part during this rebuilding period since Lee’s deal ended up being a good value as the salary cap skyrocketed in the middle of the decade. Holding onto Lee for even one more season may have produced a solid return in a trade from a playoff team. Instead, Ainge gave up an asset (second-round pick) to get off his deal. Gomes was waived immediately while Bayless played an uneventful half-season in Boston before he walked in free agency.

54. 2019 No 20 overall pick (Matisse Thybulle) for 2019 No. 24 overall pick (Ty Jerome) and No. 33 Carsen Edwards (June 2019)

There’s still plenty of time left to evaluate this one, but the early returns are not promising. Thybulle is already a defensive stud for the 76ers in year one (albeit with a very limited offensive skillset). Given the C’s shallow bench rotation, he would have been a piece that could have helped right away. The Celtics ended up flipping No. 24 for a 2020 Bucks first-round pick in the Aron Baynes salary dump with Phoenix and that is on course to be No. 30 overall in 2020. Meanwhile, Carsen Edwards has struggled mightily during his rookie season. It’s too early to make any grand declarations about this one, but the Sixers look like they got the best player in the deal.

53. 2011 No. 25 overall pick (MarShon Brooks) for 2011 No. 27 overall pick (JaJuan Johnson) and 2014 second-round pick (No. 47 - Russ Smith)

This wasn’t a bad deal in the moment, but Ainge is getting penalized here for the Johnson pick. The power forward lasted one year in the NBA while plenty of wing/backcourt help that the C’s desperately could have used was still on the board at No. 27 and went in the next five picks (Jimmy Butler, Cory Joseph, Bojan Bogdanovic).

52. The rights to Darius Songalia to the Kings for two future second-round picks (No. 56 Orien Greene, No. 53 Brandon Hunter)

The very first move by Ainge as a member of the Celtics front office was largely inconsequential in the big picture but still a net negative for Boston. Songalia was the No. 50 overall pick in the 2002 NBA Draft for the C’s and had been playing overseas prior to his arrival in the NBA after this trade. He was immediately a solid bench contributor as a 25-year-old rookie in Sacramento and had a decent NBA career. Meanwhile, Green and Hunter both lasted just a couple of full seasons in the NBA.

51. Abdel Nader to the Thunder with cash for Rodney Purvis (waived)

The rookie small forward was a victim of a numbers crunch at the end of an underwhelming first season in Green. The C’s packaged him with some cash to OKC for nothing, and Nader surprisingly turned into useful reserves for Billy Donovan during his two years there on a cheap rookie deal. Not exactly a meaningful misfire but Ainge would have been better off dumping Guerschon Yabusele over Nader in hindsight.

Coming up this week: Part 2 and debating the Kendrick Perkins for Jeff Green trade