“Trader Danny” Ainge & the Elusive Midseason Trade

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Teddy Barry

As yet another NBA trade deadline came and went Thursday in relative silence from the Celtics, I wondered about the origins of Danny Ainge’s “Trader Danny” nickname. Over his nearly 18 years leading the Celtics front office, Ainge has been known for his bold, sometimes controversial trades, dumping productive fan favorites for assets and giving up massive hauls for future Hall of Famers. But almost all of those blockbusters have come in the offseason. Recently, his nickname is a running joke among NBA fans as they watch other contenders improve via midseason trade each year while the Celtics stand pat.

With the Celtics hovering at .500 and barely in playoff contention two-thirds of the way through the season despite huge leaps from their two young cornerstones, why did Ainge let yet another trade deadline slip by? The Celtics have lost in the Conference Finals 3 of the last 4 years yet haven’t made an in-season trade since 2015. Is the Trader Danny moniker now ironically associated more with the trades he hasn’t made? (For analysis on last week’s trades and lack thereof, check out our boys at Green With Envy.)

How it Started

Ainge was hired in May 2003 as the Celtics were being swept out of the second round of the playoffs. Over the next five months he made four trade. The last one sent back-to-back All-Star Antoine Walker in all his shimmying glory to Dallas a week before the season. Celtics fans were stunned and the legend of Trader Danny was born in the media. Ainge continued with two more trades during that season, including the one that brought Ricky Davis to Boston. He took part in 12 trades in his first 28 months as GM to further cement his nickname.

Let’s be clear about something. Trader Danny’s wheelin’ and dealin’ reputation may have focused more on quantity than quality in the early years. There’s no question it set up the Celtics’ return to relevance, however. Though his early trades involved mostly forgettable names besides Walker, Davis, and past-their-prime stars like Gary Payton and Rick Fox, he also netted the picks that would turn into Kendrick Perkins, Rajon Rondo, and Tony Allen.

Sure, he could seem trigger-happy. On multiple occasions he traded away a player he had previously traded for less than a year prior. He never simply never shied away from the big deal. Only six months after bringing back ‘Toine for a second stint in Boston, Ainge traded him away again as part of a 5-team, 11-player swap, the biggest in NBA history. But he also collected crucial assets that would indirectly help the Celtics return to glory. These included the picks that would become Delonte West and Ryan Gomes.

Peak “Trader Danny”

And of course we can’t ignore the moves that changed the tongue-in-cheek tone of his nickname to one of reverence for the boogeyman who fleeced his fellow GMs at the trade table. In the summer of 2007, Ainge pulled off two daring trades for future Hall of Famers Ray Allen and Kevin Garnett. He also added important contributor and fan favorite Glen “Big Baby” Davis. Of the eight players and three picks the Celtics parted with, seven had been acquired by trade under Ainge. The rest is history. Boston won its first title in two decades. Ainge won Executive of the Year. Yada yada yada. But Trader Danny wasn’t done.

Nets Robbery

Five years later, having traded for various impact players like Brandon Bass and Courtney Lee in the meantime, Ainge struck again with the (Billy) King’s Ransom of 2013. He traded franchise icons Paul Pierce and Garnett to the Nets for a treasure chest of picks and swaps. This gifted the Celtics top-eight picks in three straight years when Pierce and KG proved to be over the hill. Now stay with me – Ainge turned two of those picks into future All-Stars Jaylen Brown and Jayson Tatum after finessing another division rival. He traded their long-coveted #1 pick to the Sixers, who drafted future bust Markelle Fultz while the Celtics took Tatum.

Before those drafts, Ainge picked up bench player and former #60 pick Isaiah Thomas in a trade for spare parts. IT turned into a two-time All-Star and the most beloved Celtic to not win a title in decades. Two years later, in a coldhearted move that left Celtics fans reeling with mixed emotions, he sent Isaiah (who was coming off a career-altering injury), the final Brooklyn pick, and three more players and picks to Cleveland for superstar Kyrie Irving. ALL of these assets had been acquired by trade. Did you get all that?

What Changed?

So what’s the problem? Well for starters, time has muddied the waters of who truly “won” those trades. The Celtics haven’t made the Finals since 2010 and everyone knows how the short-lived Kyrie era ended. But more importantly, all the trades above occurred in the offseason, aside from the IT trade which was only a home run in hindsight. The only in-season trade Ainge has made since 2015 was a Jabari Bird salary dump for a low second-round pick. Besides Isaiah, the most notable midseason trades since 2011 have landed them mostly underwhelming players like Jeff Green and Jae Crowder while shipping out stalwarts Perkins and Rondo.

This wouldn’t automatically be a problem were it not for Boston’s recent trend of coming up short in the playoffs. They always seem one or two players away from breaking through to the Finals. This happens while they sidestep rumors of interest in every superstar trade piece for the last decade.

Moniker Doesn’t Fit Anymore

Watching this team take a step back despite the growth of their young stud cornerstones while once again getting outbid for the biggest names at the trade deadline is incredibly frustrating. Maybe Aaron Gordon or Nikola Vucevic wasn’t the answer this year. Tatum and Brown are still babies by league standards – there’s still time. But at least it would have shown Ainge’s recognition of, and willingness to solve problems in real time. This is something he’s failed to do for six straight years now.

Despite his nickname’s sarcastic origins, Ainge has enjoyed the success and respect that came with it just the same. “Trader Danny” has now officially swung back into the realm of irony. Until Ainge flexes those muscles again for a notable midseason improvement, that’s where it should stay.

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Episode 48