$814 Million in 3 Days: What it's Like to Attend the Winter Meetings

This past week was my second time attending MLB’s Winter Meetings, but unlike last year in Vegas, the stove caught fire in San Diego. In perfect three act structure, we got: Monday at noon, Stephen Strasburg smashing David Price’s record $217 million for a pitcher by returning to D.C. for 7 years, $245; Tuesday night, Gerrit Cole obliterating Stras’ deal by commanding 9 years, $324 from the Yankees; and Wednesday night, Anthony Rendon grabbing his own 7 years, $245 to form an all-world triumvirate with Mike Trout and Shohei Ohtani in Anaheim.

Now, what are the Meetings actually like? Well, the center of the action is the hotel lobby—this year, at the Hyatt by the waterfront. From job-seekers introducing themselves to any executive they recognize to media members trading rumors to agents schmoozing it up, it’s a bustling scene that sees hundreds of baseball men and women congregating 24/7. I’m talking to a scout I befriended during Spring Training and then ESPN’s Jeff Passan walks right by, or I’m catching up with MLB Pipeline’s Jim Callis and see new Red Sox GM Chaim Bloom talking to Mets legend David Wright.

When the bombshell signings broke, I felt an electricity go through the lobby as everyone checked the news on their phones and started debating the wisdom of the contracts; soon after, MLB Network’s Jon Heyman and FoxSports’ Ken Rosenthal would post up in front of cameras and explain the details. At night, everyone from top team brass to college students trying to get their first baseball jobs hits the hotel bar and, facilitated by the social lubricant of liquor, many fun, irreverent baseball conversations ensue.

Some players attend, usually those who live in the city where the Meetings are hosted. One was Diamondbacks rookie Kevin Ginkel, who was born in San Diego and played community college ball in Chula Vista before transferring to University of Arizona. An absolute mountain, he’s bigger than his listed 6’4”, 210 lbs., and used this wipeout slider to post a 1.48 ERA and .99 WHIP in his 24 inning MLB debut.

I had interviewed five players from Ginkel’s agency, Ballengee Group, in the Arizona Fall League, so I introduced myself and we talked Dbacks. Having come up through the Snakes farm system, Kevin offered keen insights into how someone like lefty Alex Young developed into a Big League starter throwing just 88 to 92 mph fastballs: as the two came up through Double-A Jackson and Triple-A Reno, Ginkel noticed that Young had developed command of his pitches to both sides of the plate and that sweet spot below the knees with 2-strikes, just high enough to get hitters to swing at sinkers, cutters, breakers, and changeups. This allowed Young to surprise people with a 3.56 ERA and 1.19 WHIP over 83 innings as a rookie in 2019. Ginkel shared more observations about young Dbacks arms and believes the team can reach another level in 2020 as those players improve. Of course, yesterday’s Madison Bumgarner signing makes that outlook all the brighter!

I also caught up with a player I’d met before: Pittsburgh’s powerful righty Joe Musgrove. A graduate of Grossmont High School in nearby El Cajon (where he pitched against Pirates teammate Kevin Newman of Poway High), Joe figured he’d come out and network with agents and players. He was particularly excited about additions to the Pirates front office in GM Ben Cherington, manager Derek Shelton, and President Travis Williams.

Another highlight of my week was an hour (!!!) one-v-one conversation with legendary writer Peter Gammons. He was extremely generous with his time and sharp as ever in recounting details like, (a) the Padres had Noah Song as the top pitcher in this year’s draft, but decided not to take him unless he fell to the 5th round because of the risk his military service commitment would postpone his baseball career, or (b) Peter has known #1 overall picks Bryce Harper and Stephen Strasburg since they were amateurs, and they’ve always struggled with impossibly high expectations, but this past season Strasburg embraced how good he already is and felt the freedom to just do his thing and dominate hitters, which worked out pretty well in the Postseason! We even strayed from baseball to discuss Derek Trucks, who we agree is the world’s best guitar player and who will be playing at Gammons’ “Hot Stove Cool Music” charity benefit concert, co-hosted by Theo Epstein.

Another special moment was meeting two members of Israel’s 2020 Olympic team, utility man Ty Kelly (MLB 2016-18 for Mets and Phillies) and outfielder Blake Gailen (2019 Triple-A Dodger). Gailen played for Israel in the 2017 World Baseball Classic, when Israel shocked the world by making the quarterfinals, beating Cuba, and taking 6th in the tournament. Players on the WBC team just had to have a Jewish grandparent, but both Kelly and Gailen were required to make “aliyah” (became Israeli citizens) to play for Israel in the Olympics. Neither player was raised religiously or had been to Israel before joining the team, and both described incredibly rich experiences of visiting Jerusalem, Tel Aviv, and the Dead Sea, and of feeling truly connected to their Jewish heritage for the first time.

So beyond the straightforward news updates you saw on Twitter, that’s what the Winter Meetings are like on the ground. If you want to work in baseball, you should strongly consider attending, and if you’re just a fan who happens to be in the city where they’re being hosted (next year: Dallas), you should absolutely pop in for a day and get some selfies with baseball icons!

Follow Jacob on Twitter @TheReelJZ