Where does Kyrie Irving rank among greatest Boston sports villains? (2024)

Celtics

Roger Goodell, Bill Laimbeer, Ulf Samuelsson, and Alex Rodriguez are also noteworthy Boston-area villains.

By Conor Ryan

June 6, 2024

Asked about Kyrie Irving’s reputation in Boston, Joe Mazzulla responded with a question of his own.

“Aren’t we all in someone’s eyes? We’re all villains in someone’s eyes,” Mazzulla said on Friday.

Granted, Boston sports fandom has fixed its glare on more than just Irving over the years when it comes to the most reviled athletes to ever step foot on the parquet floor, Garden ice, Foxborough field, and plate at Fenway Park.

Irving has solidified his standing as the conduit of most Celtics’ fans collective fury over the last few seasons. But where exactly does the Mavericks guard rank among a loaded cast of Boston sports villains?

Ahead of Irving’s anticipated showdown against the Celtics in the NBA Finals, here’s a look at some of the top Boston sports villains of all time.

33. Wilt Chamberlain

Chamberlain will be one of several players on this list who might be better labeled as “adversaries” rather than outright “villains” in Boston sports.

Even though the 7-foot-1 center and prolific scorer never bested the Celtics with a title on the line, he had several battles against Bill Russell and Boston’s unequaled dynasty during the 1960s.

Chamberlain might have stuffed the stat sheet throughout his career, but you couldn’t beat Russell’s 11 titles in 13 seasons with Boston.

32. Sam Bennett

A relatively new addition to this list, Bennett, Matthew Tkachuk, and the rest of the Florida Panthers have made life miserable for the Bruins over the last few seasons.

The pugnacious Florida pivot scored five points over six games en route to the Panthers’ stunning first-round upset of a record-setting Bruins squad in 2023 — doling out plenty of punishment on the forecheck.

Bennett continued to torment the Bruins in their second-round showdown this spring, delivering a cheap-shot punch to Brad Marchand that knocked Boston’s captain out for two games. To further twist the knife, Bennett scored a controversial goal that should have been called back for goaltender interference in Game 4 that spurred the Cats to a 3-2 win at TD Garden.

31. Scott Walker

The stars were seemingly aligned for the 2008-09 Bruins, who finally broke through with a 116-point season behind a mix of established veterans and emerging young core.

But those strides were snuffed out in the second round of the Stanley Cup Playoffs at the hands of the Carolina Hurricanes. Walker, who somehow got just a paltry fine for sucker-punching Aaron Ward in Game 4, went on to score the OT goal in Game 7 at TD Garden to end Boston’s Cinderella season.

30. Tree Rollins

The 7-foot-1 Hawks center was despised by Celtics fans after biting Danny Ainge’s middle finger in the middle of a scrap during Game 3 of Boston’s first-round matchup against Atlanta in 1983.

“We got into a little scuffle out on the court by the foul line and he almost bit my finger off,” Ainge said. “He bit it all the way through. I had to get two stitches.”

The Boston Herald headline the following day? “Tree Bites Man.”

29. Alex Burrows

Much like Rollins, Burrows is still a hated figure in Boston after trying to take a chomp out of Patrice Bergeron’s hand during Game 1 of the 2011 Stanley Cup Final. Burrows was one of the poster boys for a hated Canucks squad that also featured players like Maxim Lapierre, Roberto Luongo, and Aaron Rome.

Burrows was routinely taunted by Boston for the remainder of that series, with Milan Lucic attempting to put his fingers in his mouth during a scrum in Game 3 at TD Garden.

28. Draymond Green

Granted, there are multiple cities and fanbases who would probably have Green somewhere on their list of villains. But the defensive stopper and established basketball heel was a pain throughout the Celtics’ showdown with the Warriors in the 2022 NBA Finals.

After the Warriors bested Boston and secured their latest championship at TD Garden, Green twisted the knife with multiple taunts toward the Celtics and their fans.

“I must say, it did not hurt me to watch the Boston Celtics fans suffer,” Green said on his podcast, The Draymond Green Show, last May. “Those people were really rude to me last year and I like to see them suffer.”

27. P.K. Subban

There are plenty of Habs players to choose from when it comes to Montreal’s long-standing beef with the Bruins. But Subban in particular drove Boston crazy during the latest peak of this storied rivalry in the early 2010s.

From scoring clutch playoff goals, to fighting Brad Marchand, and also helping to beat a Presidents’ Trophy Bruins team in 2014, Subban was a great antagonist during his prime years in Montreal.

“It’s going to be great,” Subban said of TD Garden ahead of Montreal’s clinching Game 7 performance in that 2014 series. “I can’t wait for the crowd, the noise, the energy in the building [in Boston]. I can’t wait to take that all away from them.”

26. Johnny Damon

This one stung. Damon was far from the first beloved Red Sox player to turn his jersey for pinstripes. But it was painful to see such a key cog in Boston’s 2004 World Series team switch allegiances just two years later.

It didn’t feel right when a clean-shaven Damon stepped up to home plate in his first game with the Yankees at Fenway Park — and the crowd let him know it.

25. LeBron James

Is he an adversary or a true villain? The crude t-shirts for sale on Causeway Street would signal he’s the latter.

But whatever he is, James long stood as a roadblock for several Celtics teams during his reign in the Eastern Conference.

The Celtics have battled James seven times in the postseason, with James winning his last five series against Boston from 2011 to 2019.

From dismantling the last run of the “Big 3” Celtics in 2012 (including a legacy-saving Game 6 masterclass at TD Garden) to vanquishing an upstart 2019 Boston roster in Game 7 of the Eastern Conference Finals, James has had many battles with Boston over the years.

24. Manny Machado

The hot-tempered Machado has made plenty of enemies over his career, especially during his early years with the Orioles. His dirty slide at second base that injured Dustin Pedroia in April 2017 prompted Eduardo Rodriguez, Matt Barnes, and Chris Sale to all throw at the Baltimore infielder over several games in the following weeks.

Pedroia was never the same after injuring his knee from Machado’s slide, only playing 98 games over the final five years of his contract before hanging up his spikes.

It was poetic justice that Sale struck out Machado swinging with a filthy slider for the final out of the 2018 World Series.

23. Terrell Suggs

The Patriots had several trash-talking adversaries on the defensive side of the ball throughout their dynasty, including Joey Porter and Bart Scott.

But Terrell Suggs stands out among that pack due to his longstanding commitment to discrediting Tom Brady, Bill Belichick, and the rest of the Patriots.

Beyond his role as a disruptive playmaker on a fearsome Baltimore defense, Suggs never missed an opportunity to chirp New England and its quarterback.

“Those are the most arrogant [expletive] in the world, starting with Coach Belichick on down,’’ Suggs said after Baltimore beat New England in the 2013 AFC championship game. “That’s funny, ever since Spygate they haven’t been able to win.’’

22. Alan Eagleson

Eagleson was the powerful NHL agent who deceived Bobby Orr en route to his eventual signing with the Chicago Blackhawks in 1976.

Despite Boston offering Orr a lucrative contract extension (even with the concern surrounding his knees), Eagleson downplayed just how hefty the Bruins’ offer was to Orr and urged him to sign with the Blackhawks instead as a free agent. It was far from the only seedy practice that Eagleson was later called out for — but it was a shame to see Orr end his career in any sweater that didn’t feature the spoked-B.

21. Tonya Harding

One of the more infamous athletes in recent memory, Harding admitted that she tried to cover up her ex-husband’s plan to take Stoneham’s own Nancy Kerrigan out of the 1994 Winter Olympics in Lillehammer, Norway.

The plan was to knock Kerrigan out of action in the lead-up to the Olympics by striking the gifted figure skater in the leg with a baton, allowing Harding to surpass her and medal at the 1994 games.

Instead, Kerrigan managed to compete in the Olympics and took home silver in 1994, while Harding didn’t medal. Harding was later banned for life from USFSA figure skating events.

20. Harry Frazee

We’re turning back the clock with this one. Even if he didn’t use his cash influx to fund a play like “No, No, Nanette”, the former Red Sox owner still shifted the entire landscape of baseball history when he decided to sell Babe Ruth’s contract to the Yankees on Dec. 26, 1919.

Hard not to put the potential architect of “The Curse of the Bambino” on this list.

19. Peyton Manning

Similar to other stars like Chamberlain or even James, Manning was a disliked figure in Boston due in large part to his standing as one of the best to ever play — and the frequent comparisons between him and Tom Brady.

While Brady has since separated himself from the rest of the pack when it comes to his reputation as the greatest QB of all time, it was a long-standing discourse throughout the 2000s and early 2010s, with clashes between the Patriots-Colts drawing more excitement than some Super Bowl games.

Much like Magic Johnson and Larry Bird burying their rivalry in their later years, it sure feels like a similar relationship between Brady and Manning these days.

18. Bill Parcells

Once viewed as a savior in New England that brought a demanding attitude and championship pedigree to Foxborough, Parcells regularly clashed with Robert Kraft and was already in the midst of planning his exit from the team after New England made it to Super Bowl XXXI against the Packers.

He went on to coach one of New England’s top rivals in the Jets from 1997-99, with his presence in New York helping to convince star running back Curtis Martin to sign a poison-pill contract with the team that the Patriots couldn’t match.

17. Bucky Dent

You know you’ve carved out quite the reputation in Boston when Red Sox fans have inserted an f-bomb into the middle of your name.

Dent only slugged 40 home runs in his 12-year MLB career, but he made many of them count — headlined by the three-run shot in the AL East Division tie-breaker game against the Red Sox during the 1978 season.

His big fly over the Green Monster gave New York a 3-2 lead in the seventh inning — with the Yankees going on to win the game, 5-4, and send a stacked Red Sox roster packing before the postseason.

16. Aaron Boone

The Bucky Dent for the next generation of Red Sox fans, Boone ended Boston’s “Cowboy Up” run in 2003 with one swing of the bat — with his first-pitch, walk-off home run in the 11th inning giving New York a 6-5 victory in Game 7 of the ALCS. It doesn’t help that Boone has now served as the Yankees’ manager since 2018.

Most Red Sox fans are still waiting for Grady Little to pull Pedro Martinez from the mound. A rewatch of that fateful Game 7 remains a brutal undertaking.

15. George Steinbrenner

The loud, boisterous owner of the Yankees for nearly 40 years, Steinbrenner was the encapsulation of the “Evil Empire” in New York that sat atop baseball for decades — standing in stark contrast to a down-on-its-luck Red Sox organization that just never seemed to get over the top.

Steinbrenner, who wielded his fiscal power to outbid the Red Sox on several top free agents, apparently flipped off the Red Sox team bus on its way out of Yankee Stadium following that Game 7 loss in the 2003 ALCS, according to Kevin Millar.

14. Rick Pitino

“Larry Bird is not walking through that door.”

Once thought of as another franchise savior in Boston, Pitino instead accelerated the Celtics’ decline into obscurity in the late ‘90s during his infamous tenure as the team’s head coach, GM, and president.

Boston’s gamble with letting Pitino wield sizable power within the organization blew up in their face, with Pitino going 102-146 in three-and-a-half seasons with the Celtics. He also traded away future Hall of FamerChauncey Billups in his rookie year for Kenny Anderson. Woof.

13. Rex Ryan

A fantastic foil to the quiet and calculating Belichick, Ryan pushed the Jets and Patriots rivalry into the stratosphere during his tenure as New York’s coach from 2009-14.

His antagonistic approach to the Patriots and unwillingness to acknowledge New England’s reign atop the NFL rubbed off on his players, which culminated in a shocking upset win over the Patriots in the 2010 AFC Divisional Round at Gillette Stadium.

“I never came here to kiss Bill Belichick’s rings,” Ryan said before his first season with the Jets. “I came to win. Let’s just put it that way. So we’ll see what happens. I’m certainly not intimidated by New England or anybody else.”

Even though Ryan never led the Jets to the promised land, he did post wins in three of his first five games against Belichick during his time in New York.

12. Matt Cooke

One of the dirtiest cheap-shot artists in recent memory, Cooke remains a hated figure in Boston for his ugly hit on Bruins star Marc Savard.

Cooke’s high elbow to a defenseless Savard set the playmaking forward on a path that ended his career due to severe concussion issues. Not only did it prompt an early end to an incredibly promising hockey career, but Savard’s post-concussion symptoms have plagued him long after he last skated on the ice in 2011.

11. Bernard Pollard

Pollard was a one-man wrecking crew whenever he seemed to face the Patriots, with the hard-hitting safety doling out four major injuries that hampered multiple seasons in New England.

Pollard’s hit against Tom Brady’s knee in Week 1 of the 2008 season knocked Brady out the rest of the year due to a torn ACL, snuffing out any hope of a revenge tour for New England after losing Super Bowl XLII.

His presence in the Texans’ backfield prompted Wes Welker to cut to his right after reeling in a catch from Brady, with the talented slot receiver tearing both his ACL and MCL in the process.

Rob Gronkowski was limited with a high ankle sprain off a tackle from Pollard in the 2011 AFC Championship Game, limiting the star tight end in a loss to the Giants in Super Bowl XLVI. Pollard later knocked running back Steven Ridley with a helmet-to-helmet hit in the 2012 AFC title game.

10. Eli Manning

Eli Manning may not have been the better quarterback over his brother. At least during the regular season.

But the Giants QB delivered on the highest stage, making Patriots fans miserable in the process. Manning and the Giants shredded New England’s hopes of a perfect season in 2007 during Super Bowl XLII, with the photo of David Tyree’s helmet catch over Rodney Harrison making most Bostonians grimace to this day.

Four years later, Manning and the Giants tormented New England again in Super Bowl XLVI — beating the Patriots in the fourth quarter off another clutch drive featuring a throw for the ages (this one reeled in by Mario Manningham).

9. Roger Clemens

One of the greatest Red Sox pitchers of all time, the “Rocket” sure made Boston pay after former Sox GM Dan Duquette said Clemens was in the “twilight” of his career after the veteran walked in free agency before the 1997 season.

Over the next two seasons, Clemens went 41-13 with the AL East rival Blue Jays — posting a 2.33 ERA, striking out 563 batters over 498.2 innings and winning two Cy Young Awards. In his first start at Fenway as a Blue Jay, Clemens fanned 16 batters on July 12, 1997 and appeared to glare at Duquette and the rest of the Red Sox’ front office sitting in the owner’s box.

Clemens went on to pitch six seasons across two stints with the Yankees, winning two World Series, another Cy Young Award, and bouncing Boston from the postseason twice in 1999 and 2003.

His high and inside pitch to Manny Ramirez in Game 3 of the 2003 ALCS also sparked a memorable brawl that ended with Pedro Martinez throwing 73-year-old Don Zimmer to the ground.

8. Ulf Samuelsson

It was a cheap shot delivered by Samuelsson against Bruins star Cam Neely during the 1991 Stanley Cup Playoffs that set the beloved power forward on the road to an early retirement.

Neely, who developed a degenerative knee condition in that affected area, only played 22 total games over the next two seasons following Samuelsson’s dirty leg check.

He went on to score 50 goals in just 49 games during the 1993-94 season, but Neely only played 162 total games over his final five seasons in the NHL before being forced to retire in 1995-96 at just 31 years old.

7. Eric Mangini

A turncoat who branched out from Bill Belichick’s coaching tree and left New England to become the Jets head coach, Mangini further betrayed the Patriots’ head coach with his role in SpyGate.

It was Mangini, who had years of experience on the Patriots’ coaching staff, who alerted NFL security that New England was taping from unauthorized areas during its Week 1 game against the Jets in 2007.

What followed was a sizable fine against Belichick, months of drama, the loss of a first-round pick, and a black mark against the Patriots’ organization.

6. Bill Laimbeer

One of the ringleaders of the “Bad Boy” Pistons, Laimbeer and his teammates like Rick Mahorn, Dennis Rodman, and Isiah Thomas made life miserable for every opponent they faced during their heyday.

The Celtics and Pistons met in the playoffs five times over a six-year run during the later stages of the Larry Bird Era in Boston, with every postseason meeting inundated with scraps on the court, errant elbows, and more dirty play that became synonymous with a player like Laimbeer.

5. Pat Riley

Another loathed individual in Boston who led the Showtime Lakers in the ‘80s, Riley was another great sports villain who served as a foil to the Celtics and their identity during those prime rivalry seasons.

Along with beating Boston twice in the NBA Finals in 1985 and 1987, Riley laid the groundwork for a Miami Heat team that — behind LeBron James, Dwyane Wade, and Chris Bosh — snuffed out the final years of contention for the “Big 3” Celtics.

Add in his still-looming presence on a Miami organization that has continued to be a thorn in the side of Boston to this day, and Riley is an easy addition to this list. He’s one of the best coaches/execs in NBA history, but a lot of that success has been to the detriment of Boston.

4. Kyrie Irving

Where do we begin?

After walking back on his commitment to re-sign with the Celtics, his passive-aggressive comments about Boston’s younger core, ditching the team in free agency, throwing up the middle finger to Celtics fans, and stomping on Lucky’s logo at midcourt … Irving is in for plenty of boos on Thursday night.

3. Alex Rodriguez

As loathed as the Yankees have been in Boston, there has always been begrudged respect dished out towards franchise stalwarts in the Bronx like Mariano Rivera and Derek Jeter.

That same courtesy was not carried over to A-Rod, to say the least. After nearly joining Boston during the 2004 offseason, Rodriguez quickly became persona non grata to Red Sox fans in his first season with the Yankees — getting into an brawl with Jason Varitek in July 2004 before slapping the ball out of Bronson Arroyo’s glove during the 2004 ALCS.

Add in his steroid scandals, his strong production at the plate, and his onerous demeanor, and Rodriguez was the type of athlete who was easy to despise by multiple fanbases.

2. Jack Tatum

Nicknamed the “Assassin” due to his knack for delivering dangerous hits in the defensive backfield, Tatum is a lock for this list after delivering an infamous hit against Patriots wide receiver Darryl Stingley during a preseason game in 1978.

The hit from Tatum permanently damaged Stingley’s spinal cord, leaving him paralyzed from the neck down for the rest of his life. Stingley, who died at age 55 in 2007 due to heart disease and pneumonia complicated by quadriplegia, said that Tatum never apologized to him for the hit, nor did he ever reach out to check on his wellbeing.

1. Roger Goodell

Sure, the Patriots and Tom Brady ultimately overcame all of the drama of “Deflategate” by winning three Super Bowls after that 2014 AFC Championship Game against the Colts.

But Goodell will not be able to take in a game from the luxury boxes at Gillette Stadium without getting showered by boos for a long, long time after the NFL’s role in that drama.

We’ll save you the frustration of recapping the frustrating twists and turns that came with the arduous ordeal that was “Deflategate”, but Goodell’s harsh punishment dished out against Brady will not be forgotten in New England any time soon.