Winter Meetings Experiences

Every year in the first full week of December, Major League (and Minor League) Baseball holds its Winter Meetings. They’re usually in a warmer climate, though that’s not always the case. They are always interesting though, no matter what your goal is as an attendant.

If you’re the paparazzi or just a star-gazer, you’ll get baseball’s version of the Academy Awards. There may not be a red carpet, but by doing a quick 360 in any large room there, you’ll see more baseball celebrities than you can count. In the years I’ve gone to the meetings, I’ve seen current and former players and managers, countless media personalities, and anyone important who’s involved in the game one way or another. Each of the three years I went, I saw Ozzie Guillen doing something equally hilarious, and it put a smile on my face each time.

In 2008 in Las Vegas, he was vehemently swearing while shopping for shoes in the Bellagio lobby. In Indianapolis the following winter, he camped out in the lobby on a comfy couch, flanked on either side by attractive women while he smoked a cigar and laughed louder than I ever have heard someone before. The following year in Orlando, Ozzie acted liked the mayor of town every single time a Major League owner, GM or manager walked by. He was way more friendly than his personality would normally allow, but it seems plenty of people act a bit different when they’re in such a large, boisterous crowd. (He was most likely searching for a job, knowing the coming season would be his last with the White Sox.)

If talking baseball is your thing, there’s no better place to absorb all the current rumors. Although there tend to be some wacky deals that someone you know’s buddy thought they overheard, you could also be the first to know when something is made official. At the Indy meetings, I remember seeing Tim Kurkjian of ESPN doing laps around the hotel lobby’s water fountain on his cell phone, switching phone conversations, then dashing away. Half an hour later, the three-way Curtis Granderson trade was announced. During the in-between time, we heard various names all over the room, like “Grandy” and “Kennedy” and “Jackson.”

Just being around so many baseball people can be rewarding in its own right. I got the chance to speak with the man who came up with the idea for the Arizona Fall League for a good fifteen minutes, even though he didn’t know me from a hole in the wall. Seeing a man who has been a GM for multiple teams, collected some World Series rings, and is considered one of the best executives to work in the game was a big enough privilege. To see how friendly and optimistic he was really inspired me, since everyone seems to think sports are a cold-blooded business like any other industry these days.

For anyone who wants a job in the minors, the PBEO Job Fair is a good opportunity to see all the current openings throughout the 150+ teams. If you’re into sales, pretty much half of the 300+ options could be a great match. For other departments, your experience will vary, though they seem to have double digits for every single type except broadcasting. (If you want to call games for a living, this is a fantastic place to get an entry-level gig and/or network with executives from minor and major league teams.)

Networking has led me to a few jobs in the past, including at the meetings, but the friendships I’ve created through meeting people there has been just as rewarding for me. I’ll give a shout out to a few of my mentors and baseball friends later this week.

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