There are moments in life when you have to stop and ask yourself, “How in the world did I get here?”
Walking into the Pennsylvania Convention Center last Saturday morning with an official MLB media credential hanging around my neck was one of those moments.
Four years ago, I wasn’t writing about baseball. I wasn’t interviewing players. I certainly wasn’t traveling across the country to cover one of Major League Baseball’s biggest events.
Yet there I was, representing South Side Sox at the 2026 MLB draft.
Sometimes, dreams really do come true.
When the White Sox secured the No. 1 overall pick in the 2026 draft back in December, my first thought wasn’t about covering the event. I simply wanted to attend.
For the past several years, I’ve helped our South Side Sox staff prepare for the draft. I’ve spent countless hours researching prospects, helping build our draft coverage, and writing about the White Sox farm system as part of our minor league recap team. Getting the chance to see the first overall selection in person felt like something every baseball fan should experience at least once.
After all, the White Sox hadn’t held the first overall pick in nearly 50 years. The last time it happened, I was only five years old. I don’t remember the draft, and honestly, I don’t remember much about baseball at all from that age.
So why not make the trip?
Then another thought crept into my head.
What if I didn’t go as a fan?
What if I went as a member of the media?
It felt almost ridiculous to even consider. Would MLB approve someone like me? Would SB Nation even want to pursue credentials?
Still, if I’ve learned anything over the last few years, it’s that the only guaranteed “no” is the one you never ask.
He immediately thought it was worth pursuing, and together we submitted a credential request through SB Nation. A few weeks before the draft, I received the email I’d been hoping for.
Suddenly, this wasn’t just a vacation. This was an assignment.
Even better, my son Sage was able to come with me. That made the trip even more special.
I was excited, but I’d be lying if I said I wasn’t nervous.
SoxFest back in January had been my first experience interviewing players and networking with other members of the media. That event suddenly felt very small compared to this.
This was Major League Baseball. The commissioner would be there. Front-office executives would be there. The newest generation of baseball stars would be there … or so I thought.
Preparation became everything.
Knowing that writing a polished breaking story from scratch wasn’t yet one of my strengths, I decided to do as much work as possible before leaving Illinois. Roch Cholowsky, Grady Emerson and Vahn Lackey had clearly separated themselves as the leading candidates for the White Sox’s first pick, so I spent the week researching all three.
By the time I boarded the plane, most of each story had already been written. My goal was simple: once the pick was announced, I could quickly add the unique details from the draft and publish a complete story.
It felt like the perfect plan.
Sage and I flew a red-eye to Philadelphia Thursday night, arriving early Friday morning.
I wanted an extra day to familiarize myself with the city, pick up my credentials, find the convention center, and simply get comfortable before everything started.
Sleep, however, was in short supply Friday night. Part excitement. Part anticipation. Part anxiety.
Saturday morning finally arrived, and after making our way to the Pennsylvania Convention Center, I had one small panic trying to figure out exactly where the draft was being held.
Melissa Sage-Bollenbach/South Side Sox
Eventually, I found the media section and immediately spotted a familiar face.
Ryan McGuffey, senior vice president of content and co-founder of The REKAP, was sitting in the front row with an empty seat beside him.
I introduced myself, sat down, and my nerves disappeared almost instantly.
Ryan couldn’t have been more welcoming. For a while, it didn’t feel like I was attending one of baseball’s biggest events. It simply felt like two White Sox fans talking baseball.
Me and Ryan McGuffey
MLB deserves credit for the presentation. The room looked fantastic. Everywhere you looked, there were draft logos, banners, digital displays, rally towels, and energetic music filling the room. It looked every bit like a major professional sporting event.
But as draft time approached, whispers began circulating throughout the media seating: Not a single player projected to go in the first 40 selections was actually there.
As the draft unfolded, commissioner Rob Manfred simply walked to the podium, announced each selection, a pre-recorded highlight package played, and then everyone moved on to the next pick.
Melissa Sage-Bollenbach/South Side Sox
No emotional walk across the stage.
No interviews with the newest members of each organization.
Compared to the NFL, NBA or NHL drafts, it felt surprisingly impersonal.
Unfortunately, it wasn’t just the players who were absent. Because the White Sox were playing later that afternoon and hosting their Alumni Home Run Derby in Chicago, no members of the front office were available in Philadelphia, either.
In fact, covering the biggest White Sox draft selection in decades were just three of us: Ryan McGuffey, Connor McKnight of CHSN and me.
As someone hoping to challenge myself as a reporter, that was disappointing.
There were no interviews to conduct. No behind-the-scenes conversations. No opportunity to ask questions that readers watching from home couldn’t hear for themselves.
It felt like a missed opportunity — not just for the media, but for the fans who had traveled from around the country expecting something more interactive than what amounted to a televised announcement with free T-shirts and rally towels.
But sometimes the story you expect isn’t the story you get. And maybe that’s OK.
Because when I look back on the weekend, I won’t remember what the draft lacked.
I’ll remember spending three days talking baseball and spending time with one of my favorite people in the world.
When in Philadelphia … Melissa Sage-Bollenbach/South Side Sox
I’ll remember sitting in the media section wearing a credential that, just a few years ago, I never imagined I’d have.
I’ll remember realizing how much my life has changed since Brett asked me about writing about baseball in August 2022, with absolutely no journalism background.
Not who the White Sox drafted first overall. Not what MLB could have done better.
The real story is that a fan who simply loved baseball took a chance on herself, worked hard, found an incredible community at South Side Sox, and one day found herself covering an official Major League Baseball event.
If there’s one thing I’ve learned over the last four years, it’s this:
Don’t be afraid to ask.
Don’t be afraid to chase opportunities that seem out of reach.
And don’t let anyone tell you your dreams can’t come true.
Sometimes, if you’re willing to put yourself out there, they actually do.
Sox Populi 208 — The 2026 draft experience from Philadelphia — 2026-07-15
It was a little hard to tell at South Side Sox given all of our normal draft features being churned out, but this year marked a wrinkle to our coverage: Actual writers on the ground to cover the event.
Melissa Sage-Bollenbach and her son, Sage, were in Philadelphia for the draft, Melissa as credentialed SB Nation media.
Now … did that turn out to be a good thing? And did Sage, donned in a UCLA Roch Cholowsky jersey and White Sox cap, get feasted on by writers and broadcasters looking for No. 1 overall draft choice material?
Tune in to learn all of the the ins, outs and power failures of the weekend experience in Philadelphia, as the pair sits down with Brett Ballantini to chat on MLB draft 2026.
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