Biggest Bargains in Recent Boston Sports History


Nowadays, it’s all about where a general manager went wrong.

“Oh, you overpaid this guy!” or “You traded so and so for that?”

You seldom hear about the times a general manager hit on a deal big time. Whether it be at a bargain price or for virtually nothing via trade, those types of deals don’t get the level of widespread appreciation that the failures do on the other side.


We’re going to take a look at some of the biggest bargain deals in recent memory for Boston sports with a spotlight on three deals from each of the four major sports teams.

Boston Red Sox

The Boston Red Sox are a tough team to praise all of the time, despite the four World Series titles since 2004. They’ll play themselves to the praise of their fans and then make a decision that leaves those same fans scratching their heads.


However, here are three of the biggest bargain moves in recent history:

June 28, 2018: Red Sox trade INF Santiago Espinal and $1.5 million to the Blue Jays for 1B Steve Pearce

In addition to the fact Pearce took home World Series MVP honors, this deal turned out to be a major bargain for Dave Dombrowski and the Red Sox. The team swung a deal with Toronto to acquire the veteran first baseman who, at the time, was sporting a wRC+ of 136.

That number was 143 with the Red Sox, with whom he became a vital fixture in the heart of a World Series-winning lineup.


As far as what the team gave up, Espinal has been solid in the Blue Jays’ minor league ranks. In 759 plate appearances since the trade, he’s sporting a .338 wOBA and a wRC+ of 113. He even got some time at Triple-A Buffalo, where he was just above average offensively.

But when you give up one lower-level prospect for an eventual World Series MVP, that goes down as a total steal.

Jan. 22, 2013: Red Sox sign 1B Mike Napoli to a one-year, $5 million contract including incentives (worth up to $13 million)

Everybody remembers the 2013 Red Sox roster as a group of players that overachieved en route to a World Series title.

Mike Napoli was certainly no exception to that. The then-32-year-old had to convert to first base full-time due to a chronic hip condition, forcing the contract to change from three years at $39 million to one year for $5 million.

Napoli showed flashes of his old self for the 2013 Red Sox, slashing .259/.360/.482 with a .367 wOBA and a wRC+ of 128 in 139 games. Those digits are certainly a tick up from his .227/.343/.469 with a .349 wOBA and 116 wRC+ in 2012. Napoli came up with big hits all season, including a couple of monster home runs in the ALCS against the Detroit Tigers.

While Napoli’s second contract with Boston wasn’t a major success, it’s hard to look at the first one and call it anything less than a bargain.

Aug. 25, 2012: Red Sox trade OF Carl Crawford, 1B Adrian Gonzalez, RHP Josh Beckett, and UTIL Nick Punto to the Dodgers for 1B James Loney, RHPs Allen Webster and Rubby De La Rosa, INF Ivan De Jesús, OF Jerry Sands, and cash considerations

This trade shocked the baseball world.

Towards the end of a season that resulted in just 69 wins, the Boston Red Sox cleaned house, ridding it of any and all underachievers or egos.

While Webster and De La Rosa were the only two who actually saw themselves in Boston’s future plans, the point of that trade was for one thing: salary relief. And it ended up working like a charm, as the team was able to sign Mike Napoli, Shane Victorino, Koji Uehara, and others to build a championship winner in 2013.

Meanwhile, the Dodgers are leading the league in silver medals since that trade.

Boston Bruins

Don Sweeney had a tough task ahead of him when he took over for Peter Chiarelli. While he traded Milan Lucic and Dougie Hamilton almost immediately, he has since rebuilt a title contender. To do that, you need to hit on a lot of different deals.

And to think, it was neither Stephen Stamkos nor John Tavares that turned the tide in favor of the Bruins, but rather those small trades and signings.

Feb. 20, 2019: Bruins trade F Ryan Donato and a fifth-round pick to the Wild for C Charlie Coyle

This one was a layup, as Coyle has blossomed into a budding star for the Bruins, who desperately needed some semblance of a Bergeron or Krejci replacement in the top six.

Although this one took a little bit of time to develop.

Coyle had just six points in 21 regular-season games following his arrival in Boston but exploded in the postseason (16 points in 24 games). The Weymouth, Mass. native was right up there with Tuukka Rask for Conn Smythe frontrunner had the Bruins been able to beat the St. Louis Blues in the Stanley Cup Final.

But Coyle didn’t enter 2019 with a hangover, as he picked up right where he left off. In 70 games anchoring Boston’s third line, he has chipped in 16 goals and 21 assists. He even signed an extension back in November.

On the other hand, Donato has just 39 points in 84 games for the Minnesota Wild.

July 1, 2018: Bruins sign G Jaroslav Halak to a two-year, $5.5 million contract

Halak lost the starting job with the Islanders thanks in large part to a goals-against average of 3.19 and a save percentage of just .908.

As a result, he wasn’t a hot commodity on the market the following summer, and he fell right into the Bruins’ lap to the tune of $2.75 per year in a contract that has paid major dividends for Boston.

One of the biggest reasons Boston had missed the playoffs or been a first-round exit in years past was that Tuukka Rask had to play north of 60 games a season. Since Halak arrived in Boston, Rask’s starts have dropped to 45 (54.9 percent) and 41 (58.6 percent), which has opened the door to him being at the top of his game in the postseason.

Halak has meant the world to Boston, and one can only wonder how his departure would affect Rask and co.

July 1, 2016: Bruins sign F Riley Nash to a two-year, $1.8 million contract

This didn’t amount to a Bruins Stanley Cup, but Riley Nash was just what the doctor ordered for Boston during his two seasons.

Nash was just an ordinary bottom-six forward in Year 1, but everyone saw his importance on the ice in Year 2. In a season where David Krejci and Patrice Bergeron each missed 18 games, Nash saw an increase in time on ice. In fact, he saw an increase of a minute-and-a-half from 13:48 to 15:25.

That increase in time on the ice translated to success, as he netted a career-high 15 goals, 26 assists, was a +16 and had a Corsi-for of 51.7 percent.

When he departed for the Blue Jackets before last season, you could see how impactful that loss was for the Bruins, thus leading them to trade for Charlie Coyle and Marcus Johansson.

New England Patriots

The Patriots have predicated themselves on manipulating cap space by signing guys below market value. It can be both a curse and a blessing, as they’ll miss out on some stars due to underwhelming them financially.

But it’s tough to argue with Bill Belichick’s ways, especially six Super Bowls later.

May 16, 2019: Patriots bring back LB Jamie Collins on a one-year deal worth $3 million

This is part of the blessing category, as sometimes players you lose will underperform their contract so badly that they’ll fall right back into your lap.

Due to contractual disputes, New England traded Collins to Cleveland in 2016. Collins underachieved and was signed well below market value ahead of the 2019 season. At times, he was a Defensive Player of the Year candidate. But overall, he was very steady for a Patriots defense that anchored the team to 12 wins and a division title.

Oct. 25, 2016: Patriots acquire Kyle Van Noy and a seventh-round pick from Detroit for a sixth-round pick

For three-and-a-half years, Van Noy was one of New England’s best defensive players. The fact Belichick got him for just a sixth-round pick seems unbelievable to think about.

While he was never a defensive captain a la D’onta Hightower or Devin McCourty, Van Noy was very effective and, at times, dominant. In 51 games for the Patriots, the BYU product tallied 16.5 sacks, 21 tackles for loss, and two defensive scores.

Many think the Patriots will be able to fill the void created by Van Noy signing in Miami, but it’s hard to see Chase Winovich or a rookie being able to immediately fill those shoes.

March 11, 2016: Patriots sign WR Chris Hogan

It’s hard to believe the Bills let Hogan walk in restricted free agency, but there are definitely no complaints coming out of New England.

Hogan was very reliable in his three seasons with the Patriots, holding a catch percentage of 62.2 percent, 12 touchdowns, and two Super Bowl rings. He even led the league in yards-per-reception in 2016.

Even though he got hurt and played just seven games with Carolina this past season, you could see how much he was missed in a Patriots receiving corps that was heavily depleted in 2019.

Boston Celtics

Danny Ainge has built a reputation lately of trying to go for the bargain deal, avoiding anything “splashy.”

He missed out on Anthony Davis, Demarcus Cousins, and Paul George, but has still kept up a reputation of fleecing opposing general managers to build a contender every season.

July 7, 2017: Celtics trade G Avery Bradley and a second-round pick to the Pistons for F Marcus Morris

This deal got received with a lot of ridicule from Celtics fans. Avery Bradley had blossomed from a Tony Allen type (defensive specialist) to a more balanced basketball player. He even became a fan favorite in Boston, despite not ever being considered a star in the NBA.

However, it was a move to trade one year of Bradley for two years of Morris. While the Celtics never made the Finals, Morris was an anchor on both ends of the floor for a team that was one win away from upsetting LeBron James’s Cavaliers without Kyrie Irving or Gordon Hayward on Boston’s side.

While the Celtics have improved on last season, they’ve had a problem scoring when the starters come off the floor, thus creating a bigger burden on Jayson Tatum and Jaylen Brown. You can sense the hole left by Morris’s departure, and that’s thanks in large part to his bulldog mentality and solid shooting ability.

Feb. 19, 2015: Celtics acquire G Isaiah Thomas from the Phoenix Suns for G Marcus Thornton and a 2016 first-round pick

This one was a no-brainer.

Isaiah Thomas had always been a good player but was never in an environment designed to let him shine. Then came Boston, and the untapped potential became unlocked on a nightly basis.

Thomas never got to live out his desire to raise banner No. 18 before getting traded for Kyrie Irving (notice that trade wasn’t listed?), but he was everything Celtics fans needed in a star and more. Whether it be on the court or in the community, Boston adored the man they called “The Little Guy.”

In two-and-a-half seasons, Thomas averaged 24.7 points per game, shot 36.8 percent from three, and was one of the league’s best closers during his tenure in Boston. This was arguably the best bargain of the 2010s for Danny Ainge.

June 28, 2013: Celtics trade Fs Paul Pierce and Kevin Garnett and G Jason Terry to the Brooklyn Nets for Fs Gerald Wallace, Kris Humphries, and Tornike Shengelia, C Reggie Evans, G Keith Bogans, and three unprotected first-round picks

Two words: Fleece. Job.

Ainge might’ve been scrutinized for trading longtime Celtics great Paul Pierce and future Hall of Famer Kevin Garnett, but he nailed this trade on the head.

A postseason-hungry Nets team pulled the trigger on this deal, and after making the playoffs twice, sent themselves into a deep rebuild. Those picks turned into Jaylen Brown, Markelle Fultz (traded for Jayson Tatum), and Collin Sexton (pick traded in the deal for Kyrie Irving).

No matter how you slice it, it’s hard to justify Brooklyn pulling off this trade, and Danny Ainge should be eternally thanking them for it as he continues to reap the benefits of having these stars.


Check us out on our socials:   
Twitter: @PTSTNews and @TalkPrimeTime
Facebook Page: Prime Time Sports Talk
Join our Facebook Group: Prime Time Sports Talk 
Instagram: @primetimesportstalk


Share this:

Balls In The Gutter
Latest News

Balls In The Gutter: The Chiefs Dynasty Builds As We Wrap Up Another Season

The season concludes as we recap the Super Bowl and what a third win means for Patrick Mahomes, Andy Reid, and this current Chiefs dynasty. We also cover if Kyle Shanahan blew an opportunity, if the rest of the festivities were good or meh, and if these teams could be back next year. Then we talk NFL honors, free agency, the draft, and our own dynasty teams.

Read More
Chris Driscoll's All American Hoops NBA Podcast
Latest News

All American Hoops Podcast: Episode 9

Chris, John, and Matt sit down on the last night before All-Star weekend to discuss teams that have been the most disappointing and impressive. They also conduct a draft of the 2024 NBA All-Stars.

Read More

Leave a Reply

Your email address will not be published. Required fields are marked *

Browse by Category:

Visit for
hard-hitting KC Chiefs coverage.