The Patriots, Bruins, Red Sox, and Celtics have made Boston the most successful sports city in the country over the last twenty years.
The Boston sports teams that makeup what we call the “City of Champions” have brought us some of the best players and moments in our team’s history. Taking it one step further, Boston sports as a whole – New England Patriots, Boston Red Sox, Boston Celtics, Boston Bruins – is a true sports dynasty.
Since the start of 2000, Boston sports have earned a total of twelve championships; which is more than any other city in the sports world.
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The New England Patriots account for six Super Bowl titles (‘01, ‘03, ‘04, ‘14, ‘16, ‘18), the Boston Red Sox four World Series Championships (‘04, ‘07, ‘13, ‘18), and the Boston Celtics (‘08), along with the Bruins (‘11), each won a championship of their own since the turn of the century.
The amount of homegrown talent that we have seen in this city over the last twenty years is incredible. Tom Brady with the Patriots, Mookie Betts with the Red Sox, Jaylen Brown and Jayson Tatum with the Celtics, and Patrice Bergeron and Brad Marchand with the Bruins, have all been drafted and developed their careers in Boston.
Boston became a free agent destination all throughout the 2000s. The city started seeing more interest from some of the top talents around the different sports teams throughout Boston.
Some players over the years who didn’t start their careers in Boston would end up coming in and wind up becoming legendary sports icons in the city. The two biggest names are without a doubt David Ortiz and Kevin Garnett.
But along the way, there have also been many other great players who have made their way into Boston and impacted the culture of Boston sports. Manny Ramirez, Ray Allen, Corey Dillon, and Tuukka Rask have all etched their names in the history of Boston sports.
What has made Boston sports successful over the years in comparison to other sports cities has been the steady consistency from the front offices and ownership. Although each team and sport is different, the ability to negotiate contracts and invest in the athletes they believe in is similar.
Let’s take a look at how differently the Boston sports teams handle their players and contracts.
New England Patriots
The New England Patriots will rarely pay top dollar or market value for any of their players. That even includes the greatest quarterback of all time and six-time Super Bowl champion, Tom Brady.
Tom Brady is now forty-two years old, and is entering his twenty-first season in the NFL. Due to a disagreement in contract negotiations, Brady is set to test out free agency for the first time in his career.
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Even after all the success, it makes you wonder how the Patriots truly value their players if they’re willing to tarnish their franchise’s legacy by letting Tom Brady walk in free agency over a dollar amount against the salary cap.
The Patriots have always paid their players far less than they could receive elsewhere in order to continuously fill the roster and build winning teams. Due to their impressive track record, the Patriots have been rather successful in retaining their players despite what the contract amounts too.
Although, the Patriots have lost their fair share of players when it comes time to negotiate contracts. Bill Belichick has a history of challenging his players to test the open market and see where their value fits around the league. He did that most recently with the staple of his defense in Dont’a Hightower.
Some other players who went up against Belichick in contract talks are Jamie Collins, Danny Amendola, and Patrick Chung. All three players failed to get what they asked for from the Patriots in regards to contracts and eventually ventured off to play for other teams.
The way an athlete feels appreciated is through the contracts their team’s give to them. With that being said, an athlete only has a certain amount of time to maximize his financial earnings as the duration of their careers is truly unknown.
Tom Brady, a six-time Super Bowl champion and three-time league MVP has never been the highest paid player. Even at forty-two years old, Brady wants to feel valued and appreciated by the New England Patriots, the team he has spent his entire career with.
Boston Red Sox
The Boston Red Sox have a history of both paying and trading their players, but it has mostly depended on who the GM or head of Baseball Operations is.
Since 2000 we’ve seen Theo Epstein, Ben Cherington, Dave Dombrowski, and now Chaim Bloom all make important baseball decisions for the Red Sox.
Epstein is more credible for some of the players he has brought into Boston through free agency, rather than players he landed in the draft. Epstein is responsible for much of the recent success of the Boston Red Sox.
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Theo is responsible for the hiring of Terry Francona and drafting monumental figures in Red Sox history like Dustin Pedroia, and Jacoby Ellsbury. Epstein has built winning teams by bringing in players like Bill Mueller, Kevin Millar, Adrian Gonzalez, Josh Beckett, Curt Schilling, Mike Lowell, and of course, David Ortiz.
In 2014, Cherington put together a deal that sent one of the most loved players and leaders on the team in Jon Lester to Oakland in exchange for Yoeneis Cespedes. Lester went on to be a key contributing factor in the 2016 season and helped win a World Series with the Chicago Cubs.
In 2016, Dave Dombrowski gave David Price an outrageous seven-year, $217 million contract, which is the richest for a pitcher in MLB history, and last year, after a great 2018 season, he gave Chris Sale a five-year, $145 million contract.
Dombrowski’s negotiations with just those two players are now negatively impacting the Red Sox.
One of the best decisions that Dombrowski made in Boston was getting a deal done with Xander Bogaerts. Bogaerts agreed to a six-year, $120 million contract through 2025. It made sense for the Red Sox to lock up one of the best offensive short-stops in baseball.
Now jump to 2020, the Chaim Bloom era for the Red Sox. Although it has just begun, Bloom quickly made his mark in the history of Boston sports by trading away Mookie Betts (arguably the second best player in the MLB) to the Los Angeles Dodgers.
It’s hard to see the trend in how the Red Sox make these types of decisions. Mostly being because they have had four different executives making important franchise decisions throughout the last twenty years.
Boston Bruins
The Boston Bruins are probably one of the only teams in Boston sports that have been able to retain their players for the duration of their careers.
It’s pretty impressive to see how the Bruins have been able to keep a majority of their players for so many years. Especially when you put into consideration how poor the contracts are in the NHL in comparison to the other professional sports.
For example, Brad Marchand, David Krejci, and David Pastrnak have all re-signed contracts that are worth less than $50 million, just to stay on the Bruins. You just don’t see that happen in many other sports or teams.
Also along the way, the Bruins have been able to keep a strong, core group of players over the years. Patrice Bergeron, Pastrnak, Marchand, Zdeno Chara, and Tuukka Rask all won the Stanley Cup in 2011 with the Bruins.
It’s a true credit to the Bruins and how the organization appreciates the players they draft and invest in. The Bruins are a veteran team, that is committed to winning and it’s that the type of culture that keeps players around for so long.
Boston Celtics
Over the years, the Boston Celtics have missed on many players in the draft who have gone on to be All-Stars in the NBA.
But some of the players they have brought into Boston from the draft have gone through the system and made their way into Celtics history. This is what is called “homegrown talent”.
Paul Pierce was drafted in the first round of the 1998 NBA draft. By 2001, Pierce and the Celtics agreed on a six-year, $79 million, rookie scale contract.
In just under three years, the Celtics saw the potential and growth from Pierce and knew they needed to lock him in for the future. The Celtics would re-sign Pierce two more times in 2006 and 2010.
In 2006, the Celtics landed a player who changed the dynamic of the team’s chemistry and was a player Danny Ainge was scouting for a long time, Rajon Rondo. The Celtics exercised their player options for Rondo two times before he signed his rookie extension worth five-years, $55 million. Rondo was a key factor in the Celtics raising their 17th championship banner.
Marcus Smart was drafted in the first round of the 2014 draft and has made a career for himself in Boston. In 2015 and 2016, after proving his defensive abilities can contribute to winning games, the Celtics exercised their player option rights for Marcus Smart. But in 2018, the Celtics agreed to sign Smart to a four-year, $52 million contract.
In more recent years, the Celtics selected two young, one-and-done players, third overall in the draft with tremendous upside in Jaylen Brown (2016) and Jayson Tatum (2017). These two guys are poised to do great things for the Celtics and to be in Boston for a long time.
The Celtics showed their belief in Jaylen Brown by using their player option in 2017 and 2018. After taking a step back in 2019, the Celtics showed their appreciation for Jaylen by re-signing him to a four-year, $100 million contract at the beginning of this season. It just goes to show how much the Celtics truly value their players.
Although Jayson Tatum is still in his rookie contract, the Celtics can already see the type of player he is becoming. In doing so, the Celtics have exercised their player option for Tatum in 2018 and 2019.
It’s obvious the Celtics are interested in Tatum being the face of their franchise and keeping him in Boston for the remainder of his career. It shows how much the Celtics value their home grown talent and are always looking towards the future for the betterment of the team.
Looking at Boston sports as a whole, the teams have given us amazing moments and memories over the last twenty years. Boston sports have accounted for sixteen total championship appearances in the last twenty years (Patriots: 9, Red Sox: 4, Celtics: 2, Bruins: 1).
After 86 years, we saw the Red Sox win their first World Series title in 2004. We watched Tom Brady evolve into the greatest quarterback of all time, and win six Super Bowls along the way.
After twenty-two years of waiting for a championship, the Celtics won it all in ‘08 and went again in ‘10. And after nearly forty-years, the Bruins won their first Stanley Cup.
Some of the most iconic moments in Boston sports include the New England Patriots being introduced as a team in the ‘01 Super Bowl after the tragedy of September 11th.
And David Ortiz addressing the city of Boston after the Boston Marathon bombings in 2013. That speech alone will go down as one of the greatest moments in the history of Boston sports.
But Boston sports means more to the city than just the performances on the field, the court, or the ice. Sports are a way of life in Boston and that’s why the “home grown” players become an important aspect to the city and the fans.