"How did you feel when you cut it?" McCutchen asked him, as Speedy trimmed the Pirates outfielder's facial hair and just touched up the dreads.
"I just woke up one day and couldn't deal with the weight I had to carry around, because it's pretty heavy, you know?" Speedy said. "Especially when you have the big ones, which we call the bangles in the islands. It's very thick and matted. I just got tired of it and came in one day and tell everyone, 'Hey, take a piece of it,' and that's it. And from that time, I've been like this."
McCutchen was there to film an upcoming MLB Fan Cave video, part of his return visit to the Major League Baseball playland down the street. You'll be able to see how they had fun with it. But it's a real subject, a real question, the two-time All-Star asks himself sometimes.
Could he see himself cutting the dreads, maybe doing it for charity?
"One day," McCutchen said. "I mean, one day I'm going to have to shave 'em. I'm not going to have my hair forever, I'm sure."
Speedy said McCutchen "wasn't mentally prepared to actually do it yet."
"He will know when the time is right," the barber said. "Different people react in different ways. To me, I just got up one day and I didn't want it anymore. I just took it off. But he has to prepare himself mentally in order to do it.
"It was strange. After having dreads for 20 years, you were carrying all this weight around for that long, it felt like 25 pounds just get out of you and that's it. So I felt good, honestly."
These are McCutchen's strings of Samson, and the thought of removal might have seemed understandable, perhaps even on his own mind, at the end of April. But not really right now. After consecutive All-Star seasons, he started this one with a subpar April, then began rounding into familiar form.
McCutchen recorded his second four-hit game of the season on Tuesday night and is hitting .438 (14-for-32) with six RBIs in his last eight contests. Since the start of last season, he leads all Major League players with eight four-hit games. His average has gone up to .275, with four homers, 19 RBIs and 19 runs.
"He believed he would hit, we believed that he would hit," Pirates manager Clint Hurdle said. "He's pretty good at holding fast, working through things, and that's what he's done. He is in a better place with his balance at the plate. But we would've been a lot more surprised if he didn't start hitting."
At the Fan Cave, McCutchen toured the new design elements, played some ping pong, played as himself on a video game. He pointed toward one of the downtown buildings beyond the center-field wall on the television screen, telling the Cave Dwellers: "I live there. That's pretty wild."
Indeed, how many people play center field in the Majors with their home looking over them?
Before going to the barber and then catching a car service to Citi Field for the start of a four-game series, McCutchen said it "feels good" to start hitting again.
"Everything seems to be clicking and working," McCutchen said. "You're not thinking about everything. All you're thinking about is just going up to bat and knowing that you're more than likely going to have a good result. Once you get that [feeling], the game slows down, and you go out and you play some good games and have a stretch where it feels like you really can't be stopped.
"You really only get yourself out if you do get out. I'm really starting to feel good, starting to warm up here, and hopefully I can continue to do well out on the field."
While at the Fan Cave shoot, McCutchen was presented by MLB with a special version of the hot pink Louisville Slugger that hundreds of batters will wield at the plate during Mother's Day games this Sunday as part of the annual initiative to raise awareness and funds to help fight breast cancer.
McCutchen was one of the guest judges for the Honorary Bat Girl Contest, along with Yankees pitcher CC Sabathia, Dodgers outfielder Matt Kemp, Royals outfielder Alex Gordon, MLB Network host and reporter Sam Ryan, and Maria Menounos of Extra TV.
The 30 Honorary Bat Girl winners, one for each MLB club, were announced on Wednesday. All of them are breast cancer survivors and each of them will be recognized during an on-field ceremony at Sunday's national day of recognition -- or at a future date in May for clubs that are on the road this weekend.
That meant McCutchen went through many submissions of nominees, either written by cancer survivors or their friends or family members.
His grandmother, Joann Thomas, is a breast cancer survivor.
"I have had cancer in my family," McCutchen said. "My grandmother defeated it. They caught it early, so she is OK. I've found out that it really can run in your family. Some have been lost. Cancer is tough, and I hope we can find a way to beat it.
"I like that I'm getting an opportunity to be a part of this. Having Mother's Day coming up ... it's just something that means a lot to me, just having people like that in your lives."