'You're so pretty': Tolle brings his mother's words with him to every start

BOSTON -- With the latest edition of Players’ Weekend on tap for MLB from Friday through Sunday, one of the three main themes is appreciation.

Red Sox rookie lefty Payton Tolle has that one nailed, and he won’t need the weekend to reflect on it more than he already does because he thinks about it -- and her -- every day.

His appreciation for the game he loves is demonstrated by the joy he pitches with, prancing around the mound with fist pumps; broadly smiling at, well, everything; taking exaggerated leaps for balls he has no chance to get to and unleashing those monster hugs to teammates in the dugout.

Without question, Tolle is a big man with a big heart. But where does this constant joy and appreciation come from?

That’s an easy one. It is from his late mother Jina, who is no longer with him. But then again, she is always with him.

Jina Tolle died in May 2024 after years of battling (but never complaining about) colon cancer, and just two months before the Red Sox made her son the 50th overall pick in the Draft.

The gift she left to the Red Sox and baseball as a whole is Payton -- one of the most refreshingly genuine characters in his sport.

“We run out there before every game in the middle of center field, and then it's like I’m having a conversation with her,” Payton said in a recent interview behind the grandstands at Fenway Park. “There's sometimes where if I need some comfort, I know that I’ve always got a fan, so that's nice. She told me to play with joy and show people why you love this game, and I get to go out there every fifth day, and I get to do that.”

So why would Tolle ever take that for granted? He flat out refuses to.

On the outside of his glove, there is an inscription: “You’re so pretty.”

That is what Jina would yell playfully to him while he was pitching in high school to loosen him up. If it seemed embarrassing at the time, Tolle now loves that he can still hear her shouting that to him. Years of perspective have given him the comforting knowledge of exactly what she was trying to do.

“It's like I hear her,” said Tolle, who broke down into tears when asked about the meaning behind the inscription. “But every game throughout high school, I'd always know Mom was there because she'd yell, ‘You're so pretty.’ Every single time, [i thought] it was meant to embarrass me for a long time, but like I found quickly, it's like she just loves me.

“So every time I look down and see that, it's my little reminder, like, ‘Hey, crap happens on the field but you're still pretty, you're still good. You're more than just a baseball player.”’

Yes, Tolle is a lot more than a baseball player. He recently became a husband to his wife, Devin, during a small but intimate All-Star break ceremony in Boston’s North End. And he is a devoted big brother to Charlie, who also has aspirations of playing professional baseball. He’s the proud son of Chad, who has provided endless support since the passing of Jina.

But more than anything, Payton Tolle is Jina Tolle’s son. He still texts her.

“I’ve got a list of people that I text every day and she's one of them and it's a string of cuss words and then ‘I love you, I miss you,’’” said Tolle.

It turns out Jina had a colorful vocabulary, something else Payton inherited from her.

“Probably my favorite quote that my mom would say was, ‘I love Jesus, but I cuss a little bit.’ So there was an edge to her,” Tolle said. “I'm thinking about some texts that she would send me sometimes, and there'd be some language in there, but it was the most endearing language possible. It’s just kind of how we talked and how she showed us that she loved us.”

There are a couple of favorites that used to frequent Payton’s text box.

This was one: “Today's a great day to be a badass. Go out there and kick ass.”

Here was another: “Just go out there and do your thing. I kick cancer's ass so you can go out there and kick theirs.”

Jina was the best combination of threading the needle between kind yet tough.

“There's a lot of grit like that my family has, and work ethic, and the constant care, and it comes from her,” Payton said.

When Tolle held his own in an electric MLB debut against Paul Skenes at Fenway Park on Aug. 29, 2025, he is pretty sure of what his mom would have said after that game.

“My mom would have said, ‘You’re a hack still,’” chuckled Tolle. “The most I'd get humbled was at home. She’d remind me, ‘Don't get too big a head because Mama can still kick your butt.’”

For Tolle, it hurts that his mom can’t experience his ascension as one of baseball’s top young pitchers in one of the few markets that could match Gina’s utter passion.

“My mom was one of the greatest people ever, and I'm biased, yes, but there's plenty of people that could tell you that too,” said Tolle. “And I feel bad [she’s not around] because she would be famous here. Boston would love her, and she'd love Boston. Any time that I get to show a little bit of her, it's special.”