7 Worst Sports Contracts in Massachusetts History

Throughout the free agency era, the Boston Red Sox, Boston Celtics, New England Patriots and Boston Bruins have inked some of the biggest names in every game. However, not every big contract has delivered big results.

In fact, some of the worst sports contracts in Massachusetts history are among the worst contracts in sports history. Here’s a look at the seven worst contracts in the history of Massachusetts sports teams:

7. David Backes (5 years, $30 million)

The Bruins last won the Stanley Cup in 2010-11, but they’ve reached the finals twice since, in 2012-13 and 2018-19. All that success has come off the back of decent drafting, trades and free-agent signings. But even the Bruins make a bad deal now and again.

The David Backes deal is one of the team’s worst. Backes was the captain and clear team leader in St. Louis after 10 years with the Blues. He could also put the puck in the net, having posted two 30-goal seasons and four 20-goal seasons over that time. The Bruins inked him to a $30 million five-year contract in 2016. Backes scored just 39 goals in a little over three seasons before Boston dealt him away.

A diverticulitis infection and surgery removing part of his colon ruined his second season with the team. He would return the next season and help the Bruins get into the 2019 Stanley Cup Final. However, Boston lost to the same squad he once captained, the St. Louis Blues. In February 2020, the Bruins gave up and traded the beleaguered Backes to the Anaheim Ducks.

About a year and a half later, Backes was out of hockey and signed a one-day contract to officially retire with St. Louis. Check the latest Bruins Stanley Cup odds.

6. Pablo Sandoval (5 years, $90 million)

MLB’s bloated contract numbers can make even a great player’s deal look bad. Of course, it looks even worse if the player gets a bit bloated himself and fails to perform up to expectations.

The Red Sox ended the Curse of the Bambino with a World Series win in 2004. They’ve had consistent success since, winning titles in 2007, 2013 and 2018. Along the way, a number of trades, free-agent signings and re-signings have contributed heavily to all the winning. However, the Sox are also guilty of having made a few bad deals.

Pablo Sandoval’s deal stands out as one of those. After helping win a third title in five seasons with the San Francisco Giants, Sandoval signed a five-year, $90 million contract with a sixth-year club option of $17 million or a $5 million buyout heading into the 2015 season. Then he came into spring training out of shape and hit .245 with 10 home runs and 47 RBI — all career lows since his first full season in the majors.

A shoulder injury ended his season after just three games in 2016. Then, more injuries and poor conditioning led to the Sox designating Sandoval for assignment after just 32 games in 2017. In the end, the team released him with close to $48 million left on his contract.

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5. Chad Ochocinco (3 years, $6.35 million)

The Tom Brady– and Bill Belichick-led New England Patriots won six Super Bowls in 17 years. Along the way, they resurrected the careers of more than a few players who failed to live up to expectations elsewhere. However, even the vaunted Pats signed a few bad deals over nearly two decades of NFL dominance.

The Chad “Ochocinco” Johnson deal comes to mind as one. Chad Johnson had officially changed his name to Chad Ochocinco after a decade with the Cincinnati Bengals when the Pats traded two draft picks for ol’ No. 85. Then, they restructured his deal, giving him what amounted to a three-year, $6.35 million contract.

Ochocinco went on to have his least productive season. He had just 15 catches and a single touchdown while amassing a lowly 276 receiving yards. He was inactive for the AFC Championship game and caught just a single ball in Super Bowl XLVI. Of course, the Patriots lost to the New York Giants in that Super Bowl, and anything short of a Super Bowl win in the Brady/Belichick era is considered a failure.

The Pats said goodbye after the Super Bowl loss, and Ochocinco went to the Miami Dolphins training camp. He was released during the preseason following a domestic violence arrest, landed in the CFL for a year, and played one game for the Monterrey Fundidores of the Liga de Fútbol Americano Profesional in Mexico before hanging ’em up.

Check this week’s Pats odds right here.

4. Joey Galloway (1 year, terms not disclosed)

Joey Galloway’s deal with the Patriots worked out to be even worse than Ochocinco’s. Galloway was a No. 1 receiver with the Seattle Seahawks for five years before they dealt him to the Dallas Cowboys.

America’s Team made him the second-highest-paid wideout in the NFL, and after tearing his ACL in year one, he was productive for three more seasons. Eventually, in 2004, the Cowboys traded Galloway to the Tampa Bay Buccaneers. After an off year, his next three with the Bucs were 1,000-plus-receiving-yard seasons.

Then, after Galloway had another rare bad year, the Tampa Bay Buccaneers released him. In 2009, the 37-year-old receiver signed a one-year contract to join the New England Patriots. Terms of the deal were not disclosed, but suffice it to say, they were bad for the Pats.

Galloway only played in three games and was a scratch in weeks four through six because he wasn’t producing, and reportedly had trouble learning the Patriots offense. They let him go in October that year.

3. Vin Baker (4 years, $56 million)

Seventeen NBA titles tie Boston with the Los Angeles Lakers for the most all-time. That places the Celtics as one of the most successful teams in NBA history. But, like any franchise, the Celtics have given out a few awful deals over the years.

Vin Baker’s deal with Boston is quite obviously one of the worst a Massachusetts sports franchise has ever made. The Milwaukee Bucks made the University of Hartford standout the eighth pick in the 1993 NBA draft. Baker made three All-Star teams and averaged 21-plus points per game in his third and fourth seasons with the Bucs before they traded him to the Seattle SuperSonics. He had four more relatively productive years in Seattle before Boston acquired him and Shammond Williams for Kenny Anderson, Vitaly Potapenko and Joe Forte.

Baker had four years and $56 million left on his contract at the time. Then-Sonics coach Nate McMillan said Seattle moved Baker because he lost his confidence. What he didn’t say was that Baker’s weight had ballooned to almost 300 pounds and his game was disappearing. Baker would later say he was an alcoholic who would binge drink in the hotel after bad games. Celtics coach Jim O’Brien also revealed that he smelled alcohol on Baker at practices. The team confronted him about it, suspended him and released him partway through his second year with the team.

Baker played in 52 games for Boston in the 2002-03 season but averaged just 5.2 points per game. He played in just 37 a season later, averaging 11.3 points per game. After his release, he bounced around the league for another couple of seasons before giving it up. He did join Dennis Rodman’s basketball diplomacy tour in North Korea in 2014, gave up alcohol, became a part of the Bucks broadcast team, and eventually landed a job as an assistant coach with the 2021 NBA champion Milwaukee Bucks.

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2. Rick Pitino (10 years, $70 million)

The Celtics’ decision to bring on Kentucky’s Rick Pitino as head coach in 1997 is one of the worst moves in the history of the storied franchise. He had turned around a downward-trending New York Knicks squad, posting a 38-44 record in year one and a 52-30 record in year two, helping New York win an Atlantic Division title and make a conference semifinal appearance. However, those were Pitino’s only two NBA seasons, and as much success as he had in the college ranks, one winning and one losing season in the NBA hardly justified making him the highest-paid coach in sports.

The 10-year, $70 million contract the Celtics gave Pitino in 1997 did exactly that. However, he failed to return the Celtics to the team’s former glory, going 36-46, 19-31 and 35-47 in his first three years with Boston. In year four, the Celts started 12-22, and Pitino waved the white flag, resigning with a 102-146 overall record and exactly zero winning seasons.

The one saving grace is that Pitino walked away from the six years and $42 million left on the contract, taking the Celtics off the hook.

Pitino was right when he famously told the press that Larry Bird, Kevin McHale and Robert Parish weren’t about to walk through the door in an effort to temper expectations. However, Kevin Garnett and Ray Allen were about to, joining existing star Paul Pierce to lead Boston to a championship within the next seven years. It turned out expectations weren’t the problem.

1. David Price (7 years, $217 million)

Pun-intended, the price was just so high, and the length so long. David Price’s seven-year, $217 million deal with the Red Sox was the richest contract for a pitcher in MLB history when he signed it, and contracts like that come with expectations that are hard for anyone to live up to.

The former Cy Young Award winner won 17 games and led the league in innings pitched in year one, but a 3.99 ERA indicated trouble ahead. Injuries derailed year two, and Price started battling with the media instead of AL hitters. He turned things around, going 16-7 in 2018. He even helped the Red Sox capture the 2018 World Series with wins in Games 2 and 5. However, a cyst on his wrist shut him down in 2019, and in 2020, the Red Sox traded him as a part of the Mookie Betts deal to the Los Angeles Dodgers.

The Sox got a title out of the deal, but at $217 million, Price carried much higher expectations than just two decent years and a single championship.

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