The Worst Atlantic Division Trades in NBA History

Staff writer Yazin Ahmed contributed to this story.

No matter the team, mistakes in the NBA can and will happen.

Look at the league’s entire history. It takes little time to find them.

In each franchise’s respective history, those mistakes via trades can prove to be consequential. With the NBA currently on hiatus, The Lead will be publishing one story a week looking at the worst trade each team has made.

Each story will be broken down by division, starting off with the Atlantic and eventually working our way through the entire league. We’ll break down the terms of the disastrous deal, provide some context and reflect on the mostly-bad impacts those moves had.

We hope you enjoy! Without further ado, we present the worst trades in NBA history from the teams in the Atlantic Division.

Boston Celtics

Yazin Ahmed: Give me a Chauncey!

Trade details:

• BOS receives: Kenny Anderson, Zan Tabak, Popeye Jones
• TOR receives: Chauncey Billups, Roy Rogers, Dee Brown, John Thomas

Before he was the main bucket for the second coming of the Bad Boy Pistons, Chauncey Billups was seen as a lost cause and another bust in the odd 1997 draft class.

It’s worth mentioning Boston originally intended to trade pick No. 3 to Chicago for Scottie Pippen, but MJ threatened retirement if it went through.

So with pick No. 3, Billups was selected and honestly, he wasn’t necessarily bad. He was averaging eleven points, four assists and 1.5 steals on some alright shooting splits (39/34/82). But ownership pressure to make the playoffs forced GM/head coach Rick Pitino to deal Billups, despite being towards the bottom of the standings.

Billups would be tossed around a lot more, having stints in Denver and Minnesota as well, before breaking out as a Piston in 2002-03. He would go on to lead them to the Larry O’Brien in 2003-04, whilst having numerous All-Star appearances, eventually calling it a career in 2014 and in 2024, being inducted into the Basketball Hall of Fame.

Kenny was a starter for those struggling 2000’s C’s teams and was nothing more than average, whilst Tabak and Popeye Jones would be off the roster by the next season. If Boston wanted full satisfaction, keeping Billups and pairing him with The Truth would have been an elite force to potentially beat the ‘04 Lakers. 

Dominic Chiappone: Bye bye, Paul

Trade details:

• BOS receives: Charlie Scott
• PHX receives: Paul Westphal, two second-round picks (1975 and 1976)

Let’s rewind the clock back to the mid 1970s.

The Celtics are in the midst of a post-Bill Russell resurgence. Boston made five straight Eastern Conference Finals and won two titles between 1972 and 1976. Leading the way was a still-dominant John Havlicek, Dave Cowens and Paul Westphal. In the middle of that run, Westphal got shipped with assets for Charlie Scott.

Boston would still go on to be dominant in ‘75 and ‘76, but things tailed off from there. The moment Scott was a Celtic, he never made the All-Star team ever again after doing so in three consecutive years in Phoenix. Westphal ended up making five All-Star games and four All-NBA teams (three first-team nods). Boston won 44, 32 and 29 games the last three years right as Westphal peaked with the Suns.

The Celtics, fortunately, redeemed themselves shortly after and drafted Larry Bird — thus ushering in that era of dominance in the eighties. Based on what played out, it isn’t the worst move out there, but it could’ve been a lot easier for Boston had Westphal remained in a Celtics jersey.

Toronto Raptors

Yazin Ahmed: Vinsanity No More

Trade details:

• TOR receives: Eric Williams, Aaron Williams, Alonzo Mourning, 2005 FRP (Joey Graham), 2006 FRP (Renaldo Balkman)
• NJ receives: Vince Carter

For nearly a decade after December 17, 2004, Toronto Raptors fans despised Vince Carter.

Vince had requested an abrupt trade from the 8-17 Raptors, but he wasn’t competing that hard it seemed with a significantly lower average of 15.9 points per game up until the trade.

Vince infamously said “I don’t wanna dunk anymore” in an interview and after this trade, he’d dominate in NJ with absolute boat loads of dunking.

Immediately after, he averaged 27.5 points to end the season and finished 13th in MVP voting.

As for Toronto, this one’s got to sting considering in 2001, right after his wing ally Tracy McGrady headed south for Orlando, Toronto rejected a deal which would swap Dirk Nowitzki and Steve Nash in exchange for Carter.

The outcome of this deal is unfortunate. Joey Graham spent four years in Toronto never amounting to much. Renaldo Balkman was a Knick by the time of the pick, as he warmed the bench at an elite level for a bunch of random teams. Mourning left the team straight after being dealt due to kidney issues, whilst Aaron Williams did literally nothing.

But a trade tree would unfold from Eric Williams as in 2006, he and Matt Bonner went to San Antonio for big Rasho Nesterovic.

In 2008, Nesterovic was packaged along with No. 17 in that year’s draft to Indiana for aging All-Star Jermaine O’Neal. And the pick turned into nothing special— just two-time All-Star Roy Hibbert and focal defensive point of very successful 2010s Pacers teams.

O’Neal was then flipped at the deadline for Shawn Marion, and as O’Neal’s contract was expiring, opened up a second max slot for Miami. Marion was then moved to Dallas, in the offseason, being a critical part of the 2011 championship Mavericks.

Eventually the trade tree died out, but yes this trade landed Chris Bosh and LeBron in Miami as well as giving Indiana and Dallas key pieces to deep playoff runs.

In hindsight, could this be the worst deal ever? 

Dominic Chiappone: Vince Carter’s dominance in Canada concludes

Trade details:

• TOR receives: Eric Williams, Aaron Williams, Alonzo Mourning, two first-round draft picks (2005 and 2006)
• NJ receives: Vince Carter

Toronto might’ve had no choice.

By 2004, superstar Vince Carter demanded (and played) his way out of wanting to be on the franchise (as Yazin explained above).

Unfortunately, the Raptors shot themselves in the foot and then some by shipping Vince off.

Health issues meant Mourning never played for the then-New Jersey Nets. The pair of Williams never fared better than as complimentary pieces. Neither of those two draft picks turned out well, either. The Raptors would go on to win 33, 33 and 27 games the next three seasons after trading Carter. It would really take until the Kyle Lowry/DeMar DeRozan/Dwane Casey era to bring the franchise back.

Meanwhile, Carter went on to make four more All-Star teams. In terms of value, it was absolutely detrimental for Toronto.

Philadelphia 76ers

Dominic Chiappone: Saying farewell to Barkley

Trade details:

• PHI receives: Jeff Hornacek, Tim Perry and Andrew Lang
• PHX receives: Charles Barkley

Philly had its fair share of disaster moves trading away superstars (including Hall-of-Fame big men Wilt Chamberlain and Moses Malone).

Shipping out Charles Barkley was a disaster in every way possible.

In his first year with Phoenix, Barkley finished top-three in MVP voting and guided the Suns to the ‘93 Finals. He would go on to remain a superstar for at least the next half-decade and keep Phoenix “in the mix.”

As for the Sixers, they went on to miss the postseason in six straight years. Hornacek was traded in ‘94 and immediately became the third-best player for the Jazz (who made the Finals in ‘97 and ‘98). Perry was out of the league by ‘96, while Lang played for one year and was gone by ‘93. 

Yazin Ahmed: The Fultz Fiasco

Trade details: 

• PHI receives: Pick No. 1 in 2017 NBA Draft (Markelle Fultz)
• BOS receives: Pick No. 3 in 2017 NBA Draft (Jayson Tatum), 2019 FRP via SAC (Romeo Langford)

“The Boston Celtics are your 2024 NBA Champions” is something that still stings Sixers fans weeks after their rivals were crowned kings of the NBA. 

What hurts even more is that they created it. In the 2017 NBA Draft, the crown jewel of the class was Washington’s Markelle Fultz. The crafty PG (at the time) had legit potential on offense and drew many comparisons to James Harden.

As Boston was competing in the Eastern Conference Finals, they simultaneously received the first pick via Brooklyn in a trade I’ll cover later. But the issue was the Celtics already had an MVP-level guard in Isaiah Thomas and a great defensive fit in the backcourt in Avery Bradley. Not to mention, a young backup bench core of Marcus Smart, Jaylen Brown and Terry Rozier being a part of the Celtics squad.

So Boston shopped the pick, and as weeks went by with Paul George and Jimmy Butler suitors, Boston finally agreed to move down with Philadelphia to pick No. 3 whilst acquiring the Sacramento Kings 2019 unprotected FRP, in exchange for No. 1.

And yeah, it definitely paid off. 

In their rookie years, whilst Fultz struggled to remember how to shoot the ball, Tatum was leading the young Celtics squad to the ECF and challenging LeBron.

And it’s gone downhill from here.

Tatum just signed a $314M contract over five years and is easily a top-five player in the league after helping Boston secure banner No. 18. Meanwhile, Fultz was injury-ridden his two years as a Sixer, and was ultimately sent to Orlando for a protected first and Jonathan Simmons at the 2019 trade deadline.

He’s shown glimpses of his old self with crafty finishing, productive passing and a progressing shot, but even more injuries have basically ended his career. He’s still sitting in free agency waiting for an opportunity, but it may not come as soon as possible as injury history has cursed Markelle Fultz’s career forever.

New York Knicks

Dominic Chiappone: A blockbuster… catastrophe

Trade details:

• NY receives: Eddy Curry, Antonio Davis, one first-round pick (2007)
• CHI receives: Tim Thomas, Jermaine Jackson, Mike Sweetney, two first-round picks (2006 and 2007), one second-round pick (2007)

In the midst of the Knicks’ “dark age,” things only got bleaker for the iconic franchise.

Long story short: New York essentially gave Chicago the rights to take All-Star LaMarcus Aldridge and eventual Defensive Player of the Year Joakim Noah in consecutive drafts (LA would get traded to Portland eventually).

The post-Patrick Ewing struggles for the Knicks only continued. The Knicks went all-in to win 33 games in ‘07, their third year missing the playoffs in a row. They wouldn’t return to the postseason until 2010-11.

It was the move that defined the 2000s Knicks, for better or worse. Mostly for worse.

Yazin Ahmed: Oh No-Ah!

Trade details: 

• NY receives: Eddy Curry, Antonio Davis, 2007 FRP (Wilson Chandler)
• CHI receives: Tim Thomas, Jermaine Jackson, Mike Sweetney, 2006 FRP (LaMarcus Aldridge), 2007 FRP (Joakim Noah), 2007 SRP (Kyrylo Fesenko) and 2009 SRP (Jon Brockman)

This one doesn’t need much of an explanation as Isiah Thomas’ post-game turtlenecks can tell you the direction of this franchise. 

OK, yes, the Knicks needed a big and a 22-year-old Curry fresh off averaging 16.1 points and 5.4 rebounds seemed decent as a fit. For New York, Wilson Chandler was decent and Curry had one solid season in 2007 — where he averaged 19.5 points and 7.0 rebounds — but one look at the team’s roster should tell you this was absolutely atrocious.

Led by a Vaseline eater (Stephon Marbury), pre-sixth-man Jamal Crawford, “The Franchise” way past his prime (Steve Francis) and Quentin Richardson, they were awful, reaching 20-30 wins for seasons in the post Ewing era.

So why they gave up their first-round picks was absolutely baffling. A roster with a young Aldridge and Noah plus Nate Robinson and David Lee could’ve been a lot more enticing to a coveted superstar in the famed 2010 offseason, rather than just a Sopranos pitch. Curry played 69 more games as a Knick after 2007 and was soon out of the league.

The Bulls got exceptionally lucky at a deal like this. The 2006 FRP turned into LaMarcus Aldridge, someone they would fumble by swapping him for Tyrus Thomas (coming in part two). Obviously, LMA was a consistent All-Star averaging 20 and 10 for many years whilst Noah was the heart and soul of the D-Rose Bulls, being arguably the best center in Chicago Bulls history.

And not paying Curry and opting for longer deals allowed for Chicago to have a max slot available for the stacked 2010 FA class. This allowed them to acquire multiple time All-Star Carlos Boozer, adding an elite threat to the squad. Essentially, Chicago acquired three future All-Stars for Eddy Curry.

Knicks fans now should be grateful that they didn’t have suffer with the issues of the 2000s Knicks teams.

Brooklyn Nets

Dominic Chiappone: A dead giveaway of The Doctor

Trade details:

• NJ receives: $2.5 million in cash
• PHI receives: Julius “Dr. J” Erving

And you thought I would just pick the KG-Pierce hijacking?

That very well might be the team’s worst deal ever. We can’t forget about this throwback of a mess, however.

The context — Julius Erving was the star of the 1970s in the ABA. By 1976, that league plus the NBA executed a merger. As part of the complicated deal, New Jersey essentially had to give Dr. J away to the Sixers for pretty much nothing. The Nets essentially had to pay the Knicks close to $5 million just to be in the NBA.

Erving would go on to continue his ascent in the NBA, winning a ring in 1983 and taking the Sixers to multiple Finals berths as the league’s most well-known superstar. From that trade onward, the Nets never won more than 47 games all the way until the Jason Kidd-led Finals years in 2002 and 2003. This trade set the entire team back for at least 25 years.

Things were weird in the seventies. That still doesn’t justify how disastrous this was.

Yazin Ahmed: NOT ALL SUPER TEAMS WIN RINGS

Trade details:

• BKN receives: Kevin Garnett, Paul Pierce, Jason Terry, 2017 FRP swap best (Kyle Kuzma)
• BOS receives: Gerald Wallace, MarShon Brooks, Kris Humphries, Keith Bogans, Kris Joseph, 2014 FRP (James Young), 2016 FRP (Jaylen Brown), 2017 FRP swap worst (Markelle Fultz), 2018 FRP (Collin Sexton)

Yep, it’s a basic pick but still the worst trade in this current era.

A top-five player in the league, the Finals MVP, a very decent starter and boat loads of cap space that allowed them to acquire a future MVP candidate and an All-Star.

Yeah, there isn’t another contender for how awful this was.

What is surprising is that the pick became Kyle Kuzma, who they flipped with Brook Lopez for D’Angelo Russell, a pretty big addition from this deal. The squad of Deron Williams, Paul Pierce, Joe Johnson, Kevin Garnett and Brook Lopez with Shaun Livingston, Jason Terry, Andrei Kirilenko, Reggie Evans and Andray Blatche off the bench should’ve been really better.

They barely edged out Toronto in seven and then lost to Miami in five. Honestly it may have been better to drop to the 4th seed, face an inexperienced Washington, then take on Indiana.

Man, that could’ve been fun. Brook vs. Hibbert, PG vs. Iso Joe, Deron Williams vs. Lance and a whole lot of role players.

Regardless, this trade sucked— no doubt about it.

To think that essentially the whole Celtics future stemmed from this is nuts. They used the available cap space on Wallace and Humphries left to get Isaiah Thomas and eventually Gordon Hayward, once all the players’ contracts were off the books. They moved IT4, Crowder and the 2018 FRP for Kyrie Irving. Eventually, Irving then got moved for Kemba Walker who was then dealt for Al Horford.

I always thought James Young could’ve been someone of talent next to Marcus Smart or as a bench presence, but that went out the window as soon as Isaiah showed up and Terry Rozier occupied the backup guard role.

That 2018 pick has always left me wondering.

There were so many rumors about Cleveland dumping it and them wanting Mo Bamba or Michael Porter Jr. Why they didn’t use it to acquire DeAndre Jordan and Lou Williams, as that would’ve severely altered how the 2018 NBA Finals may have gone?

Easily, Boston won as they gained an immense amount of talent from picks and cap space. In an unsurprising ending, Danny Ainge of course robbed the other GM.