Boston Celtics: 10 Most Regrettable Contracts in Team History

The Boston Celtics are a franchise known for their ability to put together championship teams, yet as with any organization, there have been some rather poor contracts in their history.

Whether you talk about head coach Rick Pitino, players like Gary Payton or Vin Baker, there have been some rather questionable moves that the Celtics have made.

Here are the 10 more regrettable contracts in Boston Celtics history.

No. 10: Stephon Marbury

Marbury might not have has one of the bigger contract in Celtics history, yet he played well below expectations when acquired in February of 2009. Marbury made just 1.3 million with the team in half a season.

Marbury was acquired by the Celtics after the New York Knicks and Marbury continued to publicize their disagreement and fail to comply with one another in any way whatsoever.

With the Celtics, Marbury posted 3.8 points, 3.3 assists, and shot just 34.2 percent from the field.

He was a veteran talent that the Celtics believed would make a postseason impact, although in the end that was anything but the case. Just 3.7 points per game and shooting 30 percent from the field failed to meet the team's expectations.

No. 9: Marcus Banks

Marcus Banks comes in early on this list, as his deal wasn’t necessarily the worst deal the Celtics have ever made.

Banks earned just under $ 5 million dollars in his two and half season with the ball club. The Celtics showed special interest in Banks at the point guard position, as he would prove to be no more than an average talent.

In two and a hald seasons played with the team, Banks was putting up poor numbers. Banks averaged 5.5 points and 1.8 assists per game before eventually becoming a member of the Minnesota Timberwolves in the 2005-2006 season.

No. 8: Jermaine O'Neal

Jermaine O’Neal was not the most regrettable contract by any means, yet his numbers and inability to play due to injury are enough for O’Neal to crack this list.

O’Neal made just over $ 5.7 million dollars last season as a member of the Boston Celtics. Production wise, O’Neal was putting up 5.4 points and 3.6 rebounds in just 24 games played. Of the 24 games, he would start in just 10.

O’Neal could prove to make an impact in the coming season with the team, yet after his first his season his contract certainly has the potential to be a regrettable one.

No. 7: Kedrick Brown

Kedrick Brown made just over 3.1 million dollars with the team in two seasons. These two seasons were invaluable, especially because the Celtics had high hopes for Brown as an impact player.

Not the biggest of contracts, yet it’s more so of a let-down that anything else. In his second and final full season with the team Brown was putting up 5.5 points and 3.3 rebounds in nearly 20 minutes per game.

Given that Brown was the 11th pick in the first round of the 2001 NBA Draft, the team had higher expectations for what at the time seemed to be a promising shooting guard.

No. 6: Gary Payton

Going after a player like Gary Payton seemed to be one of the better moves the Celtics could have made at the time. Payton was a critical member on the L.A. Lakers prior to the deal.

Yet like much of the players on this list, Payton fell well below expectations. The Celtics paid the guy just over $ 5.4 million in the one season he played in 2004-2005.

That year the team was arguably one of the worst in the league, going 45-37 on the year. Payton played and started in all 77 games in the regular season with the team. He averaged 11.3 points, 6.1 assists and played a solid 33 minutes per game with the team that year.

It’s not like Payton was on a veteran’s minimum during his year with the team, as $ 5.4 million is a little much for a player who was barely putting up double-figures in points and just over six assists a contest.

No. 5: Shaquille O'Neal

A potential Hall-of-Famer who has won four NBA championships was expected to give the Boston Celtics more production for his money.

Current President and General Manager of the Celtics, Danny Ainge got Shaquille O’Neal to sign with the team in August of 2010. The deal was for 2 years and $ 3 million dollars. Considering Shaq was injured for months at a time last season, he was certainly not worth the money.

Danny Ainge went out on a limb to have O'Neal become the starter in place of Kendrick Perkins, a move that arguably took a stab at the Celtics chances to make noise in last year's postseason.

You’ve got to love the Big Fella, yet his failure to stay healthy and inability to produce consistently was costly for the team.

No. 4: Wally Szczerbiak

It's tough not to like the guy. Wally Szczerbiak is a player that provides hustle and a passion for the game that most don't have.

However, paying a guy $ 11 million to post 15 points a game en route to a 33-49 season in 2005-2006 is does not justify this type of money.

No. 3: Vin Baker

Talk about an overpaid athlete that wasn’t worth even half of his pay.

Vin Baker was acquired by the Celtics prior to the start of the 2002-2003 season, as he was set to make around $ 12.4 million his first year with the team and $ 13.5 million in the 2003-2004 season.

In those two seasons, Baker played in just 89 games and averaged no more than 11 points per game.

Baker was constantly dealing with his issues off the court and was more of a distraction than anything else.  That kind of money given to a guy that missed nearly an entire season of play is the type of deal that makes an organization sick to their stomach.

No. 2: Antoine Walker

Six years, 71 million dollars for a player who helped the Boston Celtics barely make the Eastern Conference Finals one year is regrettable to say the least.

Antoine Walker was a player that made an impact on this Boston Celtics team, and even brought them to an NBA Conference Finals.

Toine was a likeable player who put up solid numbers for several seasons, yet to be given the highest contract of any Celtics player in history at the time was pushing it.

Any fan of the game could appreciate his “shimmy,” yet other than that and some All-Star appearances, Walker was certainly not worthy of that type of money.

No. 1: Rick Pitino

In 1999, the Boston Celtics would sign head coach Rick Pitino for a whopping $70 million over seven years. It was the most any Celtics player or coach had ever received to that point.

In his three years and change with the Celtics, Pitino would go just 102-146, failing to bring the Celtics to a postseason appearance. Pitino was evidently made for the college game, not the pros.

It goes down as easily the worst contract in team history.