The Celtics are one of the most storied franchises in the NBA. They dominated the sixties- winning it all in ’60, ’61, ’62, ’63, ’64, ’65, ’66, ’68, and ’69- and have more total championships than any other team, with 17.

But despite having one of the top GMs in the league (Danny Ainge), they have made some absolutely boneheaded moves. So what could they have done (or not done) to raise banner 18?

Check top 5 worst trades in Celtics history.

Honorable Mentions

HM#1- The Ice Capades (1956)

(Author’s Note: This was actually one of the greatest trades of all time. However, it was just so strange that it had to be included here.)

Part One

Celtics give- #2 pick, Ed Macauley, Cliff Hagan

St. Louis Hawks send- #2 pick

Part Two

Celtics give – one week of the Ice Capades

Rochester Royals give – Promise not to pick Bill Russell

Trading Ice shows for an all-time legend. Who knows – if this hadn’t gone through, maybe the Royals would still be in this league. Who knows?

5. Baker isn’t cooking (2002)

Celtics give – Kenny Anderson, VitalyPotapenko, Joseph Forte

SuperSonics give – Vin Baker, Shammond Williams

The East was very weak in regards to big men, a problem that Boston tried to solve with Vin Baker of Seattle. The former all-star’s season was diluted with numerous off-field issues. This trade seems small and insignificant, but look at what happened after this trade. After the ’98-’99 lockout season, Baker’s weight ballooned to nearly 300 pounds and his game suffered tremendously. While Baker was able to get his weight down to around 250 by 2002, Baker revealed that he was a recovering alcoholic who used to binge in hotel rooms and at home after playing poorly.

In an interview, Baker said Celtics coach Jim O’Brien smelled alcohol on him in practice and confronted him about it. The team suspended him and he was eventually released. So though no one incoming or outgoing in the trade played major roles, Baker was a net negative and was released within 2 years. What makes this worse is that the Celtics were either unaware or ignored rumors of Baker’s addiction, so… do your homework, Gang Green. Do your homework.

4. Raef LaFrentz (2003)

Celtics give – Antoine Walker, Tony Delk

Mavericks give – Raef LaFrentz, Jiri Welsh, Chris Mills

Raef LaFrentz was in the second year of a seven-year, $70 million contract, and never averaged more than 11.1/6.9 as a Guy In Green. Walker on the other hand, in his lone year as a Boy In Blue, averaged 14/8.3.

3. Westphal… Out of contention (1974)

Celtics give – Paul Westphal, two second-rounders

Suns give – Charlie Scott

After making 3 all-star appearances in Phoenix with 24.8 points, he never made the game in Boston- and his points dropped to 17.5. Westphal, on the other hand, made 5 all-star games in 6 seasons in Phoenix.

2. Goodbye, Mr. Big Shot (1998)

Celtics give- Chauncey Billups, Dee Brown

Raptors give- Kenny Anderson, Popeye Jones, Zan Tabak

Coach Rick Pitino felt pressured to make the playoffs, so he gave upon future all-star point guard Chauncey “Big Shot” Billups less than a year after drafting him THIRD OVERALL! FOR BONA FIDE SCRUBS! Of the players acquired, Kenny Anderson stayed the longest- until 2002, when he was traded for…

5. I-Go (away) Joe (2002)

Celtics give- Joe Johnson, Randy Brown, Milt Palacio, 1st rounder

Suns give- Tony Delk, Rodney Rogers

Yes, Seven-time all-star “Iso Joe” Johnson was briefly a member of the Boston Celtics. However, they decided to trade their tenth-overall pick just 48 games into the season. At the time, their goal was a shot at a title that season.

It didn’t work out, however, as they lost to the Nets (Yes, they were good once) in the Eastern conference finals, AND lost out on a rookie future all-star. The worst part? They had the option of trading Johnson or fellow rookie Kendrick Brown. And… they made the wrong choice.

NEXT

Top 3 Worst Trades in Cavaliers History

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