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That Time I Decided to Crash the Baseball Winter Meetings

It isn’t every day that you wake up and decide, “I’m going to crash the Winter Meetings.” But when it’s the final day, Juan Soto is going to be traded and it happens to be eleven minutes from where you live, sometimes you have swing away. So, off I went, not knowing if I would even be able to get in; this was the MLB Winter Meetings after all, surely, they had some security, or some required credentials to attend, right?

Turns out, no. I walked into the Gaylord Opryland Resort & Convention Center in Nashville, TN, a little after 9AM, as if I were walking into a local Supermarket, no one stopped me or seemed to care. I took a few steps, turned my head, and there, in all his short-king glory, was Ken Rosenthal, just standing in the Lobby, working his phone for the latest scoop.

I did it. I was at the Winter Meetings.

As a Baseball fan, this was exciting, as a Yankee fan, even more so. I mean, this was the event where we found out that Gerrit Cole was going to be a Yankee, and where – one year to the day – we feared Aaron Judge wasn’t staying with the team long-term, after a gut-wrenching typo of a tweet by Jon Heyman announced that “Arson Judge” was heading to the Giants. Turns out, he was staying in New York, but that didn’t stop me from proudly wearing my Arson Judge Meme shirt in honor of the day.

Now that I was in, I started to explore. Walking around, I came to the quick realization that this was one of the coolest hotels I had ever seen, perhaps only comparable to resorts I had been to out of the country, and I could see why MLB would choose to host the event here. As I explored throughout the day, I would walk by, and occasionally introduce myself, to a cadre of some of the most talented and well-known baseball journalists around; Tom Verducci, Mark Feinsand, Joel Sherman, Jon Heyman (who I stood as close to as I dared with my shirt on display), Meredith Marakovits of the YES Network, and the whole crew of various MLB Network shows. I even met famed news-breaker, Jeff Passan, ironically, in “passin’.”

While there was security around, and some places it turned out were “credentials only,” what amazed me was just how freely these nationally famous personalities, including former players like Chris Archer, Mark DeRosa, Jake Peavy, Eduardo Perez, Carlos Pena and Gabe Kapler were roaming, without fear of crazy fans. I later would come to find out that current free agent Domingo German was just wandering around as well. It was wild. At one point, a crowd did form around someone, and I was confused as to why, until I realized it was MLB Super-Agent (and contract villain), Scott Boras; but even he had little fear to walk around after his press gaggle had dispersed.

Around 10:30 am I bumped into Yankees beat writer Bryan Hoch, who was kind enough to engage me in conversation for a couple of minutes. By that time, we had heard that the Soto-to-the-Yankees deal was “close” and should be done soon. I remarked that I hoped pitchers Michael King and Drew Thorpe weren’t in the trade, and Bryan replied that there was little doubt they would be, because “you have to give, to get, and they need him (Soto).” Resigned to that fact, I continued to walk around and take everything in.

If we’re being honest, the Winter Meetings, while enjoyable as a spectacle, can be described as a lot of waiting around and occasionally being starstruck by various famous attendees, as for most of the day, nothing happened. Most of the time, you’d see Ken Rosenthal walking around, phone in hand, or a variety of nameless team officials heading to and from their team’s GM Suites. Perhaps the experience is different in a more transaction-filled year, but Winter Meetings ’23 was not one of those times. Everybody was waiting around for one deal to go down: Juan Soto to the Yankees. Shohei Ohtani and Yoshinobu Yamamoto? They weren’t present or even meeting with teams at the event, and most other players are waiting on them or Soto to set various markets. Sure, we got a couple of random signings like Craig Kimbrel to the Orioles on a one-year deal, or reliver Adam Cimber signing with the Angels, but that was about it.

Which brings us to the big takeaway of the day: Major League Baseball needs to do something to prevent slow-action Winter Meetings. When you think about it, the two most hyped-up events for transactions are the Trade Deadline and the Winter Meetings; these events already capture the hearts and minds of fans, but they could be dominating the news if you had as many “BREAKING” stories as possible. To have a slow, and relatively transaction free three days is not good for the sport. For example, we knew almost every detail of the Soto trade by noon, and the full trade by at least 4PM, and yet, the ever-close trade announcement never seemed to come.

I, and a handful of other diehards, ended up staying till a little after 7PM, hoping the news would become officially official, despite the Padres holding things up due to “medicals” and, I kid you not, going to the official “Professional Baseball Scouts Dinner,” but by the time the MLB Network coverage was all over, and the professionals started to pack up, it was time for me to go as well. Two-plus hours later, at 9:42PM, after most fans had gone home or back to their hotel rooms, Juan Soto was officially a Yankee. Can you imagine how amazing the reaction in the room(s) would have been if that happened at any other point in the day? And yet, it all felt so anti-climactic. Amazingly, within minutes of the Soto announcement, Jeff Passan broke the news that Pitcher Eduardo Rodriquez had signed with the Diamondbacks, and a little closer to midnight, Jeimer Candelario joined up with the Reds. Seriously? This couldn’t have happened earlier in the day?

Now, don’t get me wrong, I very much enjoyed my time at the Winter Meetings; I’m glad I decided to go and would absolutely do so again. But for the sake of the sport, and the fans who do decide to spend time and money going to an event of this magnitude, something has to be done to make it transaction-packed and limit the amount of wait-and-see boredom that inevitably comes with a slow-news day. I’m not sure what the solution would be; perhaps instituting a hard signing deadline at the Meetings that would provide incentive to sign during those three days, and then close the signing window until closer to Spring Training. I don’t know, and I do realize that would require cooperation from the MLBPA and agents like Boras, which is unlikely, but something must be done.

If you ever get the chance to go to the Winter Meetings, do it, it’s a great experience; just be prepared for what may, or may not, come. At most, you get a wild day of baseball-chaos, and at the very least, you get to create an awesome memory, which in the end, isn’t that what it’s all about?


Aaron is a Writer and communicator who has notably served on the communications team of the Westchester County Executive. Nicknamed "Mr. Baseball" in his youth, Aaron is a lifelong Yankee fan, Tino Martinez and Aaron Judge enthusiast, and a fierce defender of Craig Biggio's Hall of Fame worthiness. When he is not writing, or doing baseball related activities, Aaron is an avid foodie and culinarian. His non-baseball writing can be found at the Realety Check substack.

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