For Boston sports fans, the past twenty-five years have been everything they could hope for and more. With twelve championships between the four major sports franchises, Boston has more than any other city. Through all the titles and parades, Boston fans have been privileged to watch some historic talent lead the city over the years. Numerous top-tier, historic names have played a role in Boston sports, but let’s look at the greatest of the great. The top 12 Boston Greats Since ’98.
When I considered who deserves to make the list, I looked at a variety of factors. I went beyond their talent and production for their team and also looked into their leadership, influence, and overall impact on their franchise and the city as a whole. It was extremely tough making the final cuts, but here we go.
Among names that were considered but didn’t make the cut: Vince Wilfork, Brad Marchand, Jason Varitek, and Devin McCourty.
12. Ty Law
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The New England Patriots selected Ty Law with the 23rd overall pick in the 1995 Draft. Throughout his ten-year Patriots career, Law earned two first-team All-Pro selections and won three Super Bowls. His most memorable moment with the Patriots came during Super Bowl XXXVI, when Law intercepted Rams QB, Kurt Warner, and returned it 47 yards for the Patriots’ first score of the game. Law finished his Patriot career tied for the lead for most interceptions in team history.
Law Fun Fact: NFL Hall of Famer, Tony Dorsett, is the uncle of Law. He would often spend summers as a kid in Dallas with Dorsett.
?PICK 6?
— FOX Sports (@FOXSports) May 10, 2020
Ty Law picks off Kurt Warner and takes it 47 yards to the house!
?: Super Bowl XXXVI: Rams vs. @Patriots, airing NOW on FOX pic.twitter.com/WfdeC7TN6R
11. Manny Ramirez
Manny Ramirez‘s time as a Red Sox was nothing short of an adventure. Ramirez was one of the most dominant hitters in the MLB during his time in Boston. In eight years, Ramirez batted .312 with 274 HRs and 868 RBIs. In addition to winning the Silver Slugger award in six of his eight seasons in Boston, Ramirez was a pivotal piece in the Red Sox winning two World Series. He brought an elite bat to the middle of the order and a fun, energetic atmosphere to the locker room. To this day, Manny is one of the most beloved Red Sox players among fans.
Manny Fun Fact: In a span of 643 regular season games, Manny Ramirez had 643 RBIs. He’s the only big leaguer in the last 80 years to do so.
10. Kevin Garnett
Kevin Garnett will be the shortest-tenured Boston athlete on this list, but that should tell you about his impact during his time here. Garnett was traded to the Celtics when the team was at a breaking point. Paul Pierce had grown frustrated and General Manager Danny Ainge was under heavy scrutiny. The offseason heading into the 2008 season changed Celtics’ history with the acquisitions of Garnett and Ray Allen. Garnett immediately brought not only an elite talent but the tough leadership that carried the Celtics to a championship. His connection with the city and impact on the Celtics during his time here is shown by #5 hanging in the rafters.
Garnett Fun Fact: Garnett was well known for his nickname “The Big Ticket”. The nickname was given to him by his high school coach due to his ability to draw big crowds to games.
9. Teddy Bruschi
When you think about the players over the last twenty-five years who embodied the “Patriot Way”, Teddy Bruschi is one of the first names that come to mind. So much so, that Bill Belichick called him the “perfect player” in his 2009 retirement ceremony. Bruschi spent his entire thirteen-year career in New England, winning three Super Bowls. He brought intensity, leadership, and consistency to the Patriots’ defense as a seven-time captain.
Bruschi Fun Fact: Bruschi was a three-sport athlete in high school, playing football, wrestling, and track & field.
8. Rob Gronkowski
Since the day he was drafted, Rob Gronkowski has been one of the most dominant forces in the NFL. In nine seasons as a Patriot, Gronkowski was a focal point of the offense. On top of being a nightmare to cover defensively, Gronkowski was one of the best blocking TEs in the league. As a four-time All-Pro and three-time Super Bowl Champion, Gronkowski’s accomplishments as a Patriot are tough to match. His upbeat personality and dominant play became a fixture around New England for nearly a decade.
Gronkowski Fun Fact: Gronkowski was almost a Raider or Raven. The Raiders’ scouting department supposedly had Gronk rated as the best all-around player in the draft. The Raiders went on to select Rolando McClain in the first round. Patriots would then trade with the Raiders in round two and jump the Ravens who were eyeing the future Hall of Famer.
7. Dustin Pedroia
It may be forgotten, but Dustin Pedroia produced one of the most impressive first two full seasons of a career in MLB history. The undersized second basemen came into the majors in 2007 and quickly impressed, winning the Rookie of the Year Award and helping the Boston Red Sox win the World Series. In 2008, Pedroia took his game to the next level by winning the AL MVP, Gold Glove, and Silver Slugger awards. His time in Boston seems to be underappreciated these days. Finishing his career with two World Series titles and a .299 BA, Pedroia featured not only an elite bat but was arguably the best defensive middle infielder in the league for over a decade. Tied with David Ortiz for the longest-tenured Red Sox over the past twenty-five years, Pedroia’s impact on the Red Sox and the city of Boston should never be underestimated.
Pedroia Fun Fact: Pedroia is the only Red Sox player to ever win four Gold Glove Awards.
Once you start watching Dustin Pedroia defensive highlights, you can’t stop. pic.twitter.com/t3w9IKBlHb
— Tyler Milliken ⚾️ (@tylermilliken_) January 22, 2023
6. Pedro Martinez
When Pedro Martinez was traded to Boston in November of 1997, he was coming off a career year with the Expos. Red Sox general manager at the time, Dan Duquette, timed the trade perfectly, as he acquired Pedro entering his prime years. In seven years with Boston, Pedro posted 117 wins, with a 2.52 ERA over 203 appearances, and won two Cy Young Awards and a Triple Crown title. He was the league’s most dominant pitcher in his time with Boston and played a crucial part in ending the Red Sox’s 86-year World Series drought.
Pedro Fun Facts: In 1999 and 2000, Pedro allowed two earned runs or fewer in 46 of his 58 starts. He also led the MLB in ERA for a record five seasons (’97, ’99, ’00, ’02, ’03).
5. Zdeno Chara
On July 1, 2006, Zdeno Chara signed a five-year contract with the Boston Bruins. Standing at six foot, nine inches tall, Chara brought a physical presence like none other around the league. After being named team captain shortly after signing, Chara would go on to be one of the most impactful Bruins players in franchise history. As a seven-time All-Star, Norris Trophy winner, and 2008 Stanley Cup winner, “Big Z” was a dominant force for the Bruins for fourteen seasons. Chara currently sits third overall in games played and points among defensemen in Bruins history.
Chara Fun Fact: Zdeno Chara holds the record as the tallest player in NHL history.
4. Paul Pierce
Paul “The Truth” Pierce came to Boston as a 21-year-old kid from Inglewood, California. He had spent his childhood as a Lakers fan and naturally hated the Celtics, so coming to Boston was bittersweet to start. Needless to say, he found a home wearing green for fifteen seasons. Pierce was one of the most clutch and consistent players in the game for many years.
As the Celtics captain, Pierce spent his early years as one of the premier scorers in the league, though the front office failed to surround him with enough talent to win. Fortunately, things changed in 2008 when Boston traded for stars, Kevin Garnett and Ray Allen. The trio created the first “Big Three” that has been often copied around the NBA since. The 2008 Celtics team went on to win the team’s first NBA Championship in 22 years. Even with a long history of success and Hall-of-Fame players, Pierce is one of the greatest Celtic players in franchise history with #34 hanging high in the rafters.
Pierce Fun Fact: Pierce’s nickname “The Truth” was bestowed on him by Shaquille O’Neal after a 2001 matchup between the two players.
3. Patrice Bergeron
Nineteen years ago, Bruins fans watched an 18-year-old kid make his NHL debut. Now in 2023, Patrice Bergeron is one of the most accomplished and decorated Bruins players of all time. Earlier this season, Bergeron eclipsed 1,000 career points for the third-most points as a Bruin. As a long-time former assistant captain and current captain, Bergeron has been the most impactful Bruin since the Ray Bourque era. Combine all of that with playing a crucial and leading role in the Bruin’s 2011 Stanley Cup, Bergeron deservingly comes in at number three here for the greatest Boston athletes of the past 25 years. Another title this season for the NHL point-leading Bruins would only further cement his spot.
Bergeron Fun Fact: The Patrice Bergeron we all know and love, is actually Patrice Bergeron-Cleary. His legal name includes both last names but he stuck with just Bergeron to keep things simple as he grew up in the hockey world of Canada.
2. David Ortiz
When the Twins released David Ortiz in December of 2002, I don’t think anyone could’ve pictured what would come next. After signing with the Red Sox in January 2003, most didn’t view the transaction as a significant move. Ortiz would spend the next fourteen seasons in a Red Sox uniform, producing ten All-Star selections, seven Silver Slugger awards, and three World Series titles. He was one of the most clutch players in MLB history and played a major factor in breaking the “Curse of the Bambino” in 2004 by winning the World Series.
In addition to his on-field accomplishments, one of the most iconic Ortiz moments came with a microphone in his hand. After the devastating Boston Marathon bombings in 2013, Ortiz addressed Red Sox nation and the entire city of Boston. His words were memorable and he truly rallied everyone together as one. When we talk about an athlete having an effect on not just the team, but an entire city, Ortiz is the first that comes to mind.
Ortiz Fun Fact: In 1996, during his early years with the Mariners and their Single-A affiliate Wisconsin Timber Rattlers, Ortiz played in an exhibition game against the major league roster. The game was eventually rained out and the teams adjusted to a home run derby. Ortiz would go on to beat out both Alex Rodriguez and Ken Griffey Jr.
Not if, but when they build the David Ortiz statue outside of Fenway Park, I hope it’s from his “This is our fucking city” speech. pic.twitter.com/Y6NnvtQ7k3
— Jared Carrabis (@Jared_Carrabis) April 20, 2020
1. Tom Brady
Tom Brady is not only the greatest Boston athlete of the past 25 years, but he’s arguably the greatest athlete in the history of sports. Brady spent 20 seasons as a New England Patriot, producing 74,571 passing yards, 563 total touchdowns, three MVP awards, and six Super Bowl wins. The impact Brady had on not only all of New England, but the fans worldwide is one that may never be matched. Whether he was loved or hated, he was one of the faces of the NFL for over two decades.
Brady’s head coach for all twenty years in New England, Bill Belichick, hopped on Brady’s “Let’s Go!” podcast to discuss his career now that Brady is retired.
The greatest player. The greatest career. A great, great person. It was such an opportunity and an honor for me to coach Tom. I guess it’s got to end at some point. It’s the greatest one ever.
Bill Belichick on the “Let’s Go!” podcast
The recently retired Brady will reportedly find his way back home for a ceremony in New England. The Patriots will honor all of his accomplishments as a Patriot. But what they should also do is make it clear that no one will wear #12 in a Patriots uniform again. Retire the number and hang it in the stadium.
Brady Fun Fact: Brady wore the same shoulder pads for over 25 years. In 1995, Brady was given a pair of Douglas shoulder pads while at Michigan. He would go on keep them and use them for the majority of his NFL career.
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