Postcard from the Winter Meetings in San Diego
Your favorite newsletter saved no expense in covering all the Cubs big moves


Greetings from San Diego! Since we found out that my former employers at The Athletic are sending five writers to cover the Winter Meetings, I figured, well, they must know something big is going down so I fired up the Desipio jet and here I am.
Here’s the actual view from my hotel room:

Pretty nice, huh?
It was last minute so I ended up having to share a room. But that’s fine. He seems nice. He is a little camera shy, though.

I don’t want to brag, but a little later I’m going down to the pool.

I can see why people love to live here.
Anyway, this isn’t a travelogue, you want me to bring you all the hot dish from the hot stove league.
The first big move of the Winter Meetings was the Mets signing of Kate Upton’s husband for two years, $86.5 million contract with a third year that can vest for just $35 million. I was told by a Cubs source that they also made an offer and just barely missed getting him. What a shame.
Then, one of the big three and a half shortstops, Trea Turner signed with the Phillies for 11 years, $300 million, and you’ll never believe this, but it turns out the Cubs were really close to signing him, too. Darn the luck.
When then the Angels signed the other Carlos Estevez1 I went back to that source and you'll be stunned to know that Cubs were off by a dollar. Man, Jed's trying his best. We all just want you to know that.
One of the best things we learned on Monday is that the Cubs are seriously pursuing Xander Bogaerts and his former teammate, and the greatest Cubs free agent signing of all-time, Jon Lester is trying to help convince him to sign.
Here’s actual footage of Jon’s pitch to Xander.
“It’s not all gonna be peaches and roses, or however the saying goes.” How can Xander possibly turn the Cubs down now?
Besides, perhaps you’ve heard that as a young boy growing up in Aruba that Xander was a huge Cubs fan.
Huge.
Xander Bogaerts on watching the Cubs growing up.
— Dingers: A Chicago Cubs Podcast (@Dingercubs) 4:45 PM ∙ Dec 5, 2022
I mean he says it right there.
“Were you a Cubs fan?”
”I wouldn’t say I was a Cubs fan, but, I mean I watched a lot of Cubs games.”
The Cubs have that effect on a lot of people, Xander.
Our old pal Bruce Levine finally tired of Tweeting about Jose Abreu to report that the Cubs met with Carlos Correa on Monday.
My top source says the meeting went something like this.
“Hi Carlos. Great to see you.”
”Same here. I’m excited to be meeting with teams that will do what it takes to win.”
”OK. Well, Carlos, it was great to see you. Scott, do you validate parking?”
While Carter Hawkins was displaying the world’s largest charisma void on the awful Marquee set while Cole Wright and Ryan Dempster modeled puffer vests for no apparent reason, Carter’s boss was meeting with the real media.
Jed Hoyer says Cubs have "a lot" of offers out to free agents, not very specific beyond that.
— Meghan Montemurro (@M_Montemurro) 2:37 AM ∙ Dec 6, 2022
Hoyer: "We'll continue to make offers, whether things come to fruition or not. You never never quite know, but it won't be through a lack of putting offers out there and trying."
First off, I wish that were actually true and that 20 guys all said, “yes” at the same time to Jed’s offers, immediately bankrupting the Cubs and causing Jed to literally crap his khakis.
But, we know that if everybody he’s made an actual offer to said yes, it’d just mean David Bote somehow got another seven year extension.
Wright asked Carter how frustrating it was to see a team “your team beat six games to zero,2 the Phillies, competing for a Commissioner's Trophy?"
And Carter said, “It wasn’t frustrating at all. It told us that ‘hey we can compete with those guys.’”
No. No you fucking couldn’t. You beat them six times and you finished thirteen games behind them. You know why? Because you were worse. And, here’s a shocker, they haven’t stood still. They added another great player to a core that already has several of them, and you have zilch.
This is why Marquee doesn’t let me host that show. (The only reason, probably.) If Carter sat down to me on the evening of the first day of the winter meetings when the Cubs haven’t done anything, I’d have said:
“And now we welcome Carter Hawkins to this oddly red set of ours. Hey Carter, get out of here and go do something! Why are you sitting in the fucking lobby with us? Get to work, dipshit! You know what, never mind. We all know you have not actual duties.”
Anyway, back to Jed talking to the real media while Carter and Demp play Super Password in the lobby.
Jed Hoyer: "We have a lot of offers out there and we’ll continue to make offers. Whether things come to fruition or not, you never know. It won’t be through lack of putting offers out there and trying. Getting deals done is complicated but we’ll certainly try."
— Sahadev Sharma (@sahadevsharma) 2:41 AM ∙ Dec 6, 2022
It’s like Bleacher Nation is just writing out quotes for him now.
“We’re making offers. Will those offers be accepted? Maybe. But probably not. But, you never know. Could be. Or perhaps, no. Will it be because we didn’t try hard enough? No. Or yes! You miss 120% of the shots you don’t take. Is that how that saying goes?”
Back on Marquee, Cole and Dempster actually had this exchange.
Dempster: “We’ve seen things happen in a flurry and I expect that tomorrow. I don’t know why, I just expect there to be some action tomorrow, Cole.”
I could see it, too. Maybe the Cubs can re-sign Frank Schwindel and Andrelton Simmons in one fell swoop!
Cole: “It’s almost as if you had some brass members of the Chicago Cubs on speed dial in your phone there and you know what could be happening.”
Brass members? Sounds like Marlene Ricketts has shown somebody else her bull phallus collection.
Cole: “I’m not saying, I’m just saying. When you take a look at the market and at some of the moves that are yet to be made, of course Jed, Carter, those guys, they want to make that splash, tomorrow, it could be the day we’re looking for.”
I do like how Marquee insists on the perpetuating the myth that Carter does…anything.
Dempster: “Yeah, but make that splash in the right way. Who’s the right fit for what they’re trying to do, without kind of sacrificing the integrity of the team, but at the same time you kind of get to this turning point.”
Ahh yes, that famous Cubs “integrity.” It’s what they’re known best for.
Dempster: “Alright, the rebuild or the retool has kind of taken place, now, it’s time to start adding pieces to this puzzle, We had a great finish to the season, and the best way to keep that going, keeping the positive energy going, keeping the guys energized your organization, your team, your scouts, everybody, me included, and most importantly four fans, Add that player, add that electric player. This game is built on having stars. Add that star to your team.”
I have to say that other than the weird part where he put himself into the list of people who needed to be energized, this is 100% correct. Wait, really? Dempster making sense? He’s going to need to put on a whacky wig or pour seltzer down his pants to distract us.
But he’s right. You win with stars, the Cubs have none, and that’s what’s on sale at the winter meetings and if you don’t pay what it costs, you clearly don’t give a shit if you win or not.
Anyway, instead of sending this out on Tuesday morning, I’m going to send it Monday night just so we don’t miss any of those big Cubs signings.
And from the looks of things, the Cubs are about to sign ALL THE SHORTSTOPS!
The Cubs' interest in the free-agent shortstop market has been no secret, but according to a source, there is a scenario in which Chicago could sign two of the three remaining star shortstops, likely Xander Bogaerts and Dansby Swanson.
— Mark Feinsand (@Feinsand) 3:37 AM ∙ Dec 6, 2022
“According to a source, there is a scenario…” Oh, for fuck’s sake. Just because there’s an open bar in an agent’s suite doesn’t mean you have to drink all of it.
Anyway, more updates as the meetings move on. Probably when the Cubs sign all of the shortstops.