The Winter Meetings Experience
My week in San Diego started with a rookie mistake. I spent quite a bit of time scouting the Hilton Bayfront to get an understanding of how people traffic would flow. Trying to find the right spots to catch White Sox personal to snap photos or ask questions about their offseason targets. As I scrolled through the upcoming week’s schedule on the hotel touchscreen, it seemed odd that there weren’t any MLB events. When I asked the concierge where the MLB press conferences were, they kindly told me that was taking place at the Hyatt down the street.
Whoops.
When I finally got to where I wanted to be, it didn’t take very long to know I was in the right place. As I walked through the front doors at the Manchester Grand Hyatt, the first person I ran into was Jerry Reinsdorf. Bob Nightengale of USA Today was sharing the latest news about Gerrit Cole on how the Yankees offered seven years, $245 million. Mr. Reinsdorf would lead Nightengale to the nearby window to continue the conversation, trying to hide in plain sight.
I didn’t see any other owners at the Winter Meetings, and very few general managers in the hotel lobby, but there were always whispers being passed. Writers gossipping on that latest contracts offers, which teams were tied to free agents, and if player X was going to be traded. All the while, I was just a fly on the wall trying to soak everything in. Hoping to hear a juicy rumor tied to the White Sox that would help hold my attention until Thursday.
Well, the White Sox were mostly quiet until the Nomar Mazara trade happened. Revisiting that day, it was a pretty quick turnaround from rumor to actual trade completed. That was the peak for the White Sox. Still, in the grand scheme of baseball, it barely registers on the radar as it was announced shortly before Gerrit Cole signing with the Yankees.
After back-to-back years of lackluster activity at the Winter Meetings, it is truly exceptional that the top three free agents signed one after another. Stephen Strasburg sent a little shockwave in the hotel lobby, but it didn’t come as a big surprise he was heading back to Washington. The morning Cole signed, I polled several national writers asking how many years he was going to sign. Each of them said, “Nine years.” I should have listened more intently, knowing that may have been inside information.
Cole signing was a big surprise because earlier that day, his agent Scott Boras held court in the hotel lobby. Unlike other press conferences that are in the media room, Boras set up shop outside of radio row, which is open to the public. I decided to throw myself into the scrum just to live the experience.
If you’re claustrophobic or just not a fan of being in a tight crowd, I wouldn’t recommend it. There are so many people trying to push forward in getting video, audio, and photos of Boras. I was four rows away from Boras, and couldn’t hear him at all. That’s when I ducked out of the crowd and snapped photos from a distance. I’m not even sure Rob Manfred would draw such a gathering if he answered questions outside the media room.
Outside of the Boras presser, it was just a lot of walking around the hotel. Quickly putting in 12,000+ steps each day scanning for media folks to make an introduction, general managers, and watching MLB Network tape segments. I wasn’t alone. There were many recent college graduates job seeking dressed in their best business attire. National reporters like Jon Heyman lapped me around the hotel, texting away or making calls.
Ultimately, I failed my initial goal of running into Rick Hahn at the hotel. I did walk by him on the flight home as he was sitting in first class (Hey, the money will be spent). Like other teams, Hahn and the White Sox front office personnel stayed in their hotel suite working until they made their daily session with local media. Which brings to question the purpose of the Winter Meetings. If teams are tucked away in closed off parts of a big hotel is it necessary to make it such a big event? Do front offices have to meet face-to-face with agents to discuss their clients? Or, could it be done on Skype or FaceTime?
Maybe that idea is a too new school of an approach for a business that relishes being old school. I’m sure Brian Cashman found flying cross country was worth it after signing Cole. As we learned from Fabian Ardaya of The Athletic, Los Angeles Angels owner Arte Moreno speaking with Boras alone lead to them signing Anthony Rendon. It is still weird to think that the Winter Meetings presses teams and agents into action more than any other day of the offseason. Nevertheless, this year it produced results we haven’t seen before. Hopefully, it carries over to Dallas next year.
It was fun to be a fly on the wall and witness how the Winter Meetings actually work. It is similar to work conferences, with many people wearing badges roaming the hotel lobby and standing in line at the coffee shop. Baseball’s version just has more cameras. It would stand to make some adjustments like Jayson Stark outlined, that would be more fan-friendly. A format more like SoxFest, which is for the fans to meet players and coaches standing in long lines to get their autograph, or attend seminars. That event is vital for media as it gives outlets another chance to meet face-to-face with executives before Spring Training. If the Winter Meetings were more like MLB Fest, I think it would be a much bigger event and would generate enough excitement to help fans get through the long offseason.
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Good stuff, Josh. Thanks for sharing.
I enjoyed the morning podcasts from San Diego. It sounds like an odd experience but your end product was interesting. Good work!
Interesting stuff. Thanks for sharing! I think the face to face meetings have a big impact on getting the deals done. Technology is great, but you can really judge if someone is serious about something through meeting them in person. I would guess lots of teams and agents just weren’t serious about signing at the winter meetings the last couple years.
Hahn said as much several years ago when he was just a few years into being a GM. He said he thought he could do everything at a distance but there’s a totally different dynamic to seeing each other in person.
Josh, don’t these guys hang out at the bar anymore until the wee hours writing down trade ideas on cocktail napkins? Did you try the hotel gym – maybe some interesting treadmill talk while they watch CNN before their morning lattes?
It reminds me of a scene in The Player:
Larry Levy : I’ll be there right after my AA meeting.
Griffin Mill : Oh Larry, I didn’t realise you had a drinking problem.
Larry Levy : Well I don’t really, but that’s where all the deals are being made these days.
I’ve met Rick Hahn many a time on the New Trier ballfields where his kids play. .
The dude is a fucking tool. You have no idea how much my blood would boil watching him hobnobbing it with all of the snobby Cub fan NT parents in the stands, maybe occasionally checking his phone as he presided over yet another floundering White Sox team (I love how I don’t even need to cite a year. I probably first ran into him around 2015 but it doesn’t really matter because he was either presiding over a mediocre or downright horse shit White Sox baseball team).
He sucks and the thought of you running into him in first class is like a winter reminder of my annual summer misery.
He does not give a shit about the White Sox as much as you and I do. He’s just a dude with a white collar job that JR is unnecessarily loyal to. That’s what so deeply offends me.