What happens when a 14-year-old superfan writes to his favorite NBA and WNBA stars in the bubble?

How a letter to Gregg Popovich turned into a life-changing experience (2:03)

Making a personal connection with your favorite NBA stars is a long shot -- especially in 2020. That's why one young fan was shocked when he got a response to a letter he wrote to legendary NBA coach Gregg Popovich. (2:03)

ON A SWELTERING Sunday in July, a 14-year-old basketball superfan walks to a mailbox in central Connecticut. He holds 14 letters and fans them out like a poker hand, before pushing them through the mail slot. Some are addressed to his favorite NBA and WNBA players. Others, to his favorite coaches. All of them are written, by hand, with some words of encouragement, some questions about the basketball bubbles and one simple, final question: Can I have your autograph?

He approaches the mailbox with a general suspicion that this might all be a colossal waste of time. In a year in which the mail has somehow become a political issue, the boy doesn't even know whether letters can penetrate the bubble, and his 14 notes are addressed to some of the biggest basketball stars in the world. Would any of the recipients even get the letter, let alone read it and then go out of their way to send a response? Yeah, this was a fun exercise, he thinks, but no way anybody bothers.

The boy, Bentley Baker, is a family friend of ours. He is a basketball junkie who came with me to ESPN's campus two years ago with one burning desire. When he walked into the lobby of the building I work in, he stopped like God had just paused his PS4. "Do you ... do you think we might see Woj?" he said that day, frozen in his tracks at the idea of running into ESPN's scoopmaster general, Adrian Wojnarowski. I told him maybe, and we proceeded on. He asked me a million questions about the NBA that day, about his beloved Boston Celtics and about ESPN. I got a big kick out of a kid with that kind of passion.

Two years later, and two weeks before that sweaty walk to the mailbox, Bentley and his dad, Andy, were in my backyard talking about how they were going to miss going to Celtics games this year. They were expressing the sadness so many of us sports fans felt this year, the loss of the magic of being in a packed arena, with the music booming and a random beach ball bouncing through the crowd, when that moment hits you that LEBRON IS RIGHT THERE. When you saw that John Elway or John Daly or Serena Williams was a real human being, just walking around, waiting to do their thing for us. Millions of us didn't have that in 2020, a year in which athletes and fans moved farther apart than ever before.

As we talked in the backyard about what being at games meant to him, I asked Bentley if he'd ever tried to get an autograph from a player or coach. He gave me a quizzical look. Kids these days take their phones to games, of course, not a pen and paper. Why beg for a scribbled-down autograph when a selfie is a mere arm's length away?

And so I made the case. I told Bentley how I used to write to athletes when I was a kid and ask them for their signatures. I told him about my stunning success rate, as evidenced by the mound of signed photos, magazines and sports cards still taking up space in my basement. I told him about an undercover project I did in 2010 for ESPN where I wrote almost 500 letters to players, coaches and mascots. I closed my soliloquy -- and a pretty good one, if I dare say so myself -- with what I hoped would be a big walk-off moment.

"And besides, Bentley, last time I checked, you can't sign a check using a selfie," I said.

Even as the words escaped my mouth, I realized how absurd they sounded. A 14-year-old in 2020 has a pretty good chance of never signing a check. Autographs? Mail? Checks? What other vital aspect of 1992 could I push on him? Fax machines and beepers?

But he was intrigued. He didn't have any signatures from athletes, he said, and in fact had never written a letter. He seemed excited about the possibility of trying it, this strange way of communicating.

So we came up with a project: He'd write letters to basketball players and coaches of his choosing. If anybody responded, I'd reach out and ask why it mattered so much to get back to a curious kid in Connecticut. We all chuckled because we knew nothing would come of it.

And then ... something came of it.

WHEN MY PARENTS divorced in the mid-1980s, I turned to sports memorabilia as a calm, safe place. My dad busted his ass to get me and my two younger brothers to card shows and shops on the weekend. My mom encouraged me to try a new experiment: writing letters to athletes and coaches. That was our thing. As we splintered into two different houses, it was nice to have something special to us. Just me and her.

For Christmas when I was 10, she got me several books of stamps and 500 envelopes with my name already printed in the return address area, fully unleashing me upon the sports world to ask for signatures in return. And the returns were awesome, a new adventure every time the mail carrier pulled up in front of our house in rural Pennsylvania. I got an autographed picture back from Tony Dorsett where he spelled my name "Rayn" by accident. I got a signed ball back from my favorite manager, Tommy Lasorda, who let me know "You and the Dodgers are both the best." Perhaps my favorite was a 1988 signed letter from legendary Dallas defensive tackle Randy White, who apologized for the team sucking so hard the previous year. Perhaps it was best that he didn't know how much this Giants fan hated the Cowboys.

Then one day my mom told me she had gotten the family tickets to go to an Orioles game. Sure, seeing my first MLB game in person was cool. But ... "I just want to get autographs!" I told her. My letters had been mere scrimmages for this, my autograph Super Bowl.

That day in Baltimore, my mom smuggled us down past ushers to lurk outside the Red Sox dugout, and my head practically exploded when I spotted Mike Boddicker -- the Mike Boddicker, standing 50 feet away! -- along the foul line. Boddicker was deep in conversation with a fan, raising up one finger to indicate that he'd be right with us, when my mom asked for his time. But after several more minutes of waiting, my mom could take it no more, terrified that the heat (a 75ish usher who looked like Danny DeVito's out-of-shape dad) would come for her at any moment. "Can my son have your autograph?" she asked again.

"Give me one minute," Boddicker reiterated.

My mom waited 15 more seconds before saying, "Come on, my son really wants to try to get autographs and we have limited time," she implored.

"Hey, I am in the middle of talking to another fan," Boddicker said, mildly frustrated, and for good reason.

"F--- you, Boddicker!" my mom replied, an outburst I had never seen from her before ... and I loved it. (A source close to my mom says this is ludicrous, a figment of a young boy's fertile imagination, that it was kids day at the ballpark and we were encouraged to be down there, and also, she never would yell at someone like that, and she certainly wouldn't swear, and even if she had, she wouldn't have said the actual word, she would have definitely said the letter "F" instead of the whole word, but yeah, none of that happened, Ryan. Either way, well, it was kids day and he should have signed.) Regardless, we stomped off, and I was never prouder to be my mom's son. I eventually landed a Chris Hoiles signature from the other dugout before we got booted back to our section.

By the moment we sat down in our seats for the game, my relationship with my mom had forever changed. She had fought for me against the Villainous Darth Boddicker of the North. It made me feel like she'd fight for me forever.

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When I told my mom about this autograph project and asked about the Boddicker incident, her memory was fuzzy at first but then she got rolling. She rattled off other games she took us to after the Orioles game, and later that Saturday, she sent me a slew of pictures she'd taken of me getting autographs as a young boy. "Geez, I am so glad you remember that stuff," she says. "As a parent, you make mistakes, and you end up spending so much of your life thinking that your kids are going to remember those moments."

"But instead, we remember heartwarming stuff like our mom yelling 'F--- you' at a famous baseball player," I say with a laugh.

I'm reminded of that Orioles game as I walk to the mailbox that day with Bentley and his dad. I ask them questions about basketball, and they banter back and forth about the state of the NBA. They love the Celtics, for sure, but Bentley wants to be a GM someday and his NBA knowledge is off the charts. He and Andy joke about Ben Simmons' 3-point-line-phobia and it's like listening in on a father-son version of PTI.

Before he drops the letters into the mailbox, I take a series of photos. Some of him with the letters. Some of him and his dad with the letters. Some of both of them after the letters have been sent on their way. Back at the house, we set up a text chain so they can alert me if anything arrives in the mail. I suspect we'll probably never use that chain again.

TWO WEEKS LATER, on Monday, Aug. 3, my phone buzzes with a new text. It's from Bentley: "First letter is back."

I feel a flutter in my stomach like I used to get when my mom would walk into my bedroom with a package from someone I'd written to. You never know what might be in that envelope, but you know there's something in there that connects you with someone you look up to, a hero you reached out to and prayed maybe they would reach back with a little piece of themselves.

I can't handle the suspense, so I ditch a work meeting to call Bentley. He answers and puts me on speaker with his dad. They excitedly tell me they'd received an envelope with Bentley's note in it. The responder had taken Bentley's letter and written three annotations throughout the letter, with a signature at the bottom.

"So who's it from?" I ask.

"Pop," Bentley says.

"Gregg Popovich?"

"Yep," he says.

He sends me a picture of the letter, and it's a work of art. Bentley's teenager handwriting fills the entire page, save for some white space where his paragraphs ended.

Bentley had concluded his note by asking Popovich if he had any tips about becoming a coach or front-office NBA person, and if he could have the coach's autograph. Popovich had responded by writing in the white spaces, squeezing in three thoughts:

  • "To Bentley, make education and honesty your priorities and you will be happy and at peace. Gregg Popovich"

  • "Keep a strong work ethic. Be humble and empathetic."

  • "A sense of humor is mandatory! All the best. Me again. Coach Pop"

Bentley and I spend a few minutes cackling like goats about his final line. It's not so much that it's a hilarious joke, but it was our joke, with Gregg Popovich.

At the end of the call, our hopes soar for the remaining 13 letters. I kid around with Bentley that the response is amazing -- but also daunting, considering the promise I'd made to try to interview anyone who replied. "Of all the people in sports to get a beautiful letter from, you pick the one guy who seems less interested in interviews than Bill Belichick," I tell him.

Because seriously, what are the chances I'll be able to catch up with Popovich to discuss the story? Still, today is a day to celebrate -- who knows what magic will land in Bentley's mailbox tomorrow? Or the next day?

BUT THE DAYS roll by with mailbox crickets. For almost two months, Bentley doesn't receive anything. We begin to suspect that maybe we'd struck gold once and that hoping for more was being greedy. I come to learn that the NBA bubble mailing center was receiving about 1,000 packages a day. The chances of getting even one letter back were slim. We weren't the only ones on earth who had this idea, apparently. We had just hit the lottery with Pop.

Even without a flood of responses, a cool thing was happening. The mail bug had gotten into our systems. I decide to write to my grandparents, just to say hi and that I loved them. A friend says her son had read my baseball cards story and thought it was cool that his mom knew someone who worked at ESPN. So I write him a letter and pack in some sports cards from my collection -- it feels like an adoption process. Around my birthday on Nov. 3, I get a delightful letter from my mom; so do each of my three daughters. I hand each girl a special handwritten note from Grandma, and make sure to stand there and just look at their faces. All three girls' eyes widen at their notes, each one unique to them.

Andy reconnects with some old letters his dad had left behind for him when he died -- the letters were notes Andy had written from boarding school to his dad, who saved every one of them. Bentley spends a few weeks developing a list of other players and coaches who might receive the 15th letter he'd ever mailed. He eventually settles on four retired NBA stars, and I track down their addresses.

In the meantime, I begin to think about the best way to try to get to Popovich, whose opinion of media interviews ... well, you've seen the TV sideline interviews. They're usually shorter than the first half of this sentence.

But on Sept. 29, I receive an excited text from Bentley: Another letter has arrived, this time from the Wubble. "We got a response today from Breanna Stewart!" Bentley texts me. Inside: a small photo of Breanna Stewart, signed by the WNBA superstar.

We give it a few more weeks, 'til right after the NBA bubble and the WNBA Wubble have closed up shop for the season. I reach out to Stewart's team to see if I can get her on the phone to tell her about the project. But what about Popovich -- there's no way he'd ever do an interview, right?

Then it dawns on me that for this story, there was only one way to shoot my Pop shot. On Oct. 21, I sit down and write a one-page letter explaining the project, the impact his letter had had on a 14-year-old kid in Connecticut, and ask him for 10 minutes on the phone.

Ten days later, I'm on my way to pick up my daughter from dance class when I miss a call. From a San Antonio area code. More specifically, from the AT&T Center. No, I think. Please. No, tell me I didn't miss a call from Gregg Popovich.

I listen to the voicemail and ... sure enough, it was Gregg Popovich. He had left a very kind voicemail saying he'd received my letter and wanted to give me a try. He said he rarely uses this particular number, but maybe he'd try me again. He ended the message by saying, "Stay safe. Go vote."

I call back immediately, and it goes to an arena voicemail. I leave a message. But I feel like I blew it. I save the number in my phone as "Spurs" just so it'll be obvious on the off chance he ever calls back.

Two days later, right after lunch that Monday, I'm sitting in my bedroom when the phone lights up and starts buzzing. I look down, and my heart goes into overdrive.


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I PICK UP the call and hang on every word for 12 minutes. When we're done, I immediately touch base with Bentley and his dad to get together to listen to the interview as soon as we could.

It takes a few days to book it, and in the meantime, I have a lovely interview with Breanna Stewart about the power of the autograph, too. When I get to his house, Andy is sitting in the front yard, three chairs set up 6 feet apart from each other in a small circle. Bentley comes outside, holding the Breanna Stewart photo and the Popovich note, which they've had framed and hung on his bedroom wall.

We decide to listen to both interviews, starting with Popovich. I put my phone on the ground between us, then hit play. We must have been quite a picture for passersby, three people in the middle of the yard staring at a phone on the ground like I'd discovered new Zapruder footage.

For the next 12 minutes, Bentley and his dad exchange smiles as Popovich describes how he loves responding to "genuine people," and Bentley seemed like that to him. He says he learned to respond to everybody who reaches out to him when he spent a year at North Carolina, where he watched Dean Smith carefully manage any and all fan outreaches. "I always told myself if I was ever in a position where people actually felt like writing to me, for whatever reason, I would do my best to respond," Popovich says.

He admits he doesn't love autographs, and he describes how he'll approach a crowd waiting for him outside an arena or hotel and ask anybody who's 12 years old or younger to raise their hand, then sign autographs only for the kids. Bentley gets a big kick out of the idea that he is 14 and he snuck in under the age maximum.

When I ask Popovich about how much special effort went into such a thoughtful response, he says, "Well, the bubble did afford us a little extra time, Ryan." I have to pause the tape for a moment because we're cackling like goats again.

There's something about that one sentence that embodies the advice he put into his response to Bentley -- he uses humility and humor in those 11 words to offset the work behind his note -- and all of the other Bentleys who are out there in the world. Popovich had sat down in his room one day and read Bentley's words, and contemplated, really contemplated, what thoughts to send back to him, and then hustled to address an envelope and make sure it exited the bubble.

I hit play again, and we start talking specifically about the mail. Popovich has a deep fondness for the written letter -- "It makes everything special," he says -- and it remains his favorite form of communication. "I hate Zoom, I hate emails, I despise texting because I have to respell things 50 times," Popovich says. "But when you sit down and you write a note to somebody, it's like reading a book in your hand, instead of from a Kindle. Getting back to people, I think it makes an impact."

Once we hit the 12-minute mark, Popovich says that I'm probably tired of listening to him go on and on and that he's gotta run, anyway. He ends by saying, "I hope Bentley does well. I'm glad to be able to continue to make him smile."

When the interview is done, I pick up the phone and ask Bentley how he feels. He doesn't say anything. He's still looking at the spot on the ground where the phone had been, the letter from Popovich on his lap. He finally looks at me and says, simply, "Do you see the smile on my face?"

Now Bentley and Andy want to hear the Stewart tape. She had called me from Russia, where she's playing after an incredible comeback season from a devastating Achilles injury the year before. Stewart just might be in the midst of the greatest basketball career any human has ever had: She's 26 years old with a video game résumé that includes an Olympic gold medal, two WNBA titles, two WNBA Finals MVPs, four NCAA titles and four Most Outstanding Player trophies at UConn. Oh, and throw in one big-time new fan: Bentley and Andy are already conspiring to get to the next Seattle Storm-Connecticut Sun game in Uncasville. "She's soooooo good," Bentley says.

She also has one of the most artistic autographs you'll ever see. It's an elegant stacked signature, first name on top, last name interlocking on the bottom, with her number, 30, set intricately to the right of her name. As I hit play on my interview with Stewart, I tell Bentley and his dad that my favorite part of the conversation with Stewart is when we discuss how she developed her signature -- because of how much she had to argue with legendary UConn assistant coach Chris Dailey about letting her sign with her own flair. "She always wanted us to write out all the letters in our name," Stewart says. "But I found one that works for me, where I can cross my T's together and put my number in there. You gotta have something that is recognizable, and I think mine is."

Even in high school, Stewart says in the interview, she had gotten autograph requests. By the time she got to UConn, she was getting up to 20 requests a week, which she dutifully responded to at the coaches' office. In the WNBA, she has taken great care to respond as much as possible and was particularly blown away in the Wubble by letters from people like Bentley. "Fans had to work a little harder to send it to the bubble and figure out where we were staying," Stewart says.

She continues on. She says she can't wait for next season, when she hopes fans are back in the stands. She says she misses the vibe of crowds, even hostile road arenas, and says she missed posing for selfies and signing autographs in 2020. For now, mail is that lifeline for her to feel her fans. "That person-to-person interaction is definitely missing in the sports world right now," she says. "I enjoy doing it. These opportunities might not be here forever. I'm always going to do my best to respond to someone who takes the time to reach out to me."

When the Stewart interview is over, we all sit back and I ask Bentley and his dad what they think about all of this -- the autographs, the handwritten notes, the power of mail. "I wasn't expecting too much," Bentley says. "They're busy people, obviously, so it's ... hard to explain how much the responses mean to me."

His dad says he's not very sentimental, that he doesn't hang on to much. But now he pauses for a moment, some emotion caught in his throat. "I'm going to say something weird and overarching," he says, pointing at the Popovich letter. "We all know we're going to die, right? And Bentley's going to have stuff after I'm dead and gone. And I knew, just looking at that letter, that's one of those things. That's pretty cool."

ON THE WAY home, I think about what Popovich said about the mail, and then I think about the movie "The Postman."

Yes, that's right. "The Postman," the 177-minute clunker from Kevin Costner in 1997.

Like most human beings who watched it, I didn't necessarily like the movie, but I always admired its central premise: that in difficult times, in a scary world, there's something about a handwritten letter that just feels warm and fuzzy. That a day can be going badly and then the mail carrier drops off something that restores just a little bit of your belief in humanity. "The Postman" won five Razzies and might very well have deserved more, but I stand by the notion of mail as a thread through our history. It's a dying form of communication, for sure. We're at a point where all of us, me included, shoot off emails and texts and Slacks and book Zooms and Hangouts rather than actually hanging out.

But in a COVID era, allow me to evangelize on behalf of the letter making a big comeback this holiday season. I'll be spending the holidays quarantined with my wife and kids in Connecticut this year, not with extended family in Pennsylvania, for the first time in my life.

So I'll be writing as many letters as my hands can support. It might not be the same as sitting in my grandparents' living room and trading gifts, but it'll be a thoughtful exchange of love, sent 300 miles for 50 cents. And before I leave his house, Bentley tells me he will also be busy writing -- he is sending letters to his four retired heroes in the coming weeks. (He is giddy a few weeks later when Danny Ainge replies with his autograph.)

When I pull into my driveway and I work through the list of people I want to write to, two more names pop into my head. One is a certain major NBA newsbreaker whose autograph would be the ultimate Woj bomb in Bentley's mailbox.

The other is an old friend who was busy the last time I tried connecting with him. I find his address -- he's retired, living in Kansas -- and I go inside and immediately grab a pen and paper. I'd say this apology note to Mike Boddicker is long overdue.