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10 of the most iconic mustaches in Red Sox history as Payton Tolle keeps the tradition going

From Luis Tiant’s handlebar to Payton Tolle’s Nick Offerman-approved 'stache, a former Red Sox pitcher ranks10 of the most iconic mustaches in franchise history.
ByAnthony Ranaudo
May 22, 2026; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Payton Tolle (70) heads out to the bullpen before a game against the Minnesota Twins at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images
May 22, 2026; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Payton Tolle (70) heads out to the bullpen before a game against the Minnesota Twins at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | IMAGN IMAGES via Reuters Connect

In some universe out there, Nick Offerman has a son, and he's a nasty left-handed pitcher for the Boston Red Sox. At least, that's how Offerman sees it.

The Chicago Cubs fan, actor and comedian who plays Ron Swanson (Parks and Rec) appeared on "The Joy of Baseball" podcast. He praised Payton Tolle for the skills and fun he brings to the game, and also took full credit for the mustache, joking that he could be his father. Tolle fired back with "Come to my arms papa," on social media which might be the most exciting Red Sox news of the offseason, so far.

If you hadn't noticed the resemblance before now, I'm sorry for pointing it out, because you won't be able to unsee it. When you put the two side by side you really need a DNA test to tell them and the mustaches apart.

I visited High-A Greenville last year, and Drive general manager Eric Jarinko told me he was the most impressive pitcher he'd ever seen, and one of the coolest, most down-to-earth guys, too.

Tolle is doing his part to fit in with the Red Sox, not just on the field but in Red Sox facial hair history, as well. Facial hair has always been part of the Red Sox identity, so we found the most iconic mustaches ever worn in a Sox uniform. We mostly stuck to household names and ranked them on accolades, history and a few personal connections. If you want to go down the rabbit hole yourself, this isn't the first time BoSox Injection has shown love to Red Sox mustaches — we covered the subject back in 2014, and for Sox fans this list gets really in the weeds, enjoy.

10 of the most iconic mustaches in Red Sox history as Payton Tolle keeps the tradition going

Luis Tiant

El Tiante gets the top spot because he wore No. 23, the number I was going to wear before I was traded from the Red Sox (I even had to ask for his blessing) and he was still rocking the stache then. The handlebar went with a one-of-a-kind windup, and he won 20 or more games three times in Boston.

Payton Tolle

The personality, the parted pencil mustache Over the Monster called "a statement," and the electric stuff are why he ranks this high. He went 9-6 with a 3.03 ERA and 171 strikeouts this year, and is officially endorsed by Offerman.

Dwight Evans

"Dewey" played in Boston from 1972 to 1990 and grew the mustache in the '80s as he became one of the AL's top hitters. He later served as a special advisor to the general manager and was always around spring training when I was there, a super nice, soft-spoken guy.

Wade Boggs

I grew up a Yankee fan, so I remember him clean-shaven in pinstripes. But I always heard how historic he was in Boston, along with the reputation: allegedly 64 beers on a flight, and fried chicken before every game.

Jerry Remy

RemDawg's mustache followed him from second base to the NESN booth, and he was part of the NESN crew. He's got to get some love.

Dennis Eckersley

He went 20-8 with a 2.99 ERA in his first Boston season, then reinvented himself as an electric closer on his way to Cooperstown. He also broadcast for NESN and is deeply missed in the booth.

Eck in the booth
Aug 3, 2017; Boston, MA, USA; Hall of Fame pitcher and Boston Red Sox broadcaster Dennis Eckersley in the NESN TV booth before the game between the Boston Red Sox and the Chicago White Sox at Fenway Park. Mandatory Credit: Winslow Townson-USA TODAY Sports | IMAGN IMAGES via Reuters Connect

Jim Rice

Rice hit 382 homers, won the 1978 AL MVP, and kept the mustache through all of it.

Alex Bregman

His Tom Selleck-style mustache lasted until June 6, 2025, when he shaved it between innings against the Yankees to spark a rally. It didn't work, but it's an iconic moment in modern Red Sox pop culture.

Garrett Richards

He started his in 2020 when the pandemic shut down camp, and he told WEEI, "My wife absolutely hates it, bless her heart." A Boston radio show challenged him to curl the ends up Rollie Fingers-style.

Bill Buckner

This is not a slight, because most Red Sox fans have a sour taste in their mouths, but he shouldn't be reduced to one grounder. He had 2,715 hits and a 1980 batting title, and the mustache deserves better than a footnote.

Honorable mentions go to Rod Beck's fu manchu, Tony Armas' afro-and-mustache combo and Jody Reed, whose lip helped start that 2014 list in the first place.

The 2013 beard era took over Boston's upper lip for a while, but mustaches are creeping back, and Tolle has one of the best in baseball right now. This franchise has never been short on characters, from Tiant's windup to Bregman's mid-game shave. Pedro Martinez called Tolle "a bully," and he fits right in. If he keeps this up, he could be a face of this franchise for years, and the mustache will be right there with him.

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