Obsessive Top Shortstop Watch: Is It the First Big Move for the Cubs? Yankees' Possible Pivot, Other Teams Being Annoying, More

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Obsessive Top Shortstop Watch: Is It the First Big Move for the Cubs? Yankees’ Possible Pivot, Other Teams Being Annoying, More

Chicago Cubs

Last night, Jon Heyman pegged the Cubs as the favorite to land free agent shortstop Dansby Swanson, with the Braves obviously still in the mix. Reactions were all over the place, and I think there is space for all of them. Swanson is a good player whose presence would improve the Cubs. Swanson is also likely the fourth best shortstop on this year’s market. I think conflicted feelings are OK on this one, though I remain of the mind that you can’t COUNT on the Cubs getting one of the other three shortstops when there are eight+ teams involved, and if the Cubs at least landed Swanson, it’s not like I’d complain. Even if I still prefer Carlos Correa by a good clip.

Elsewhere from the world of the top four shortstops …

  • Gordon Wittenmyer spoke with Dave Kaplan about the Cubs and the shortstops, and his perspective is that the shortstop market might play out first for the Cubs. He also thinks that teams may have to act quickly on at least some of the shortstops, because there are way more than four interested teams. Personally, I would be surprised if the Winter Meetings end without at least one of the four having signed.
  • Also, just a general note from watching Wittenmyer’s interviews, and reading his pieces this offseason: you get the sense that Wittenmyer does not think it’s out of the question that the Cubs land one of these shortstops. He seems surprisingly positive, to be honest.
  • If the Yankees start to get the sense that they won’t retain Aaron Judge, Buster Olney writes that they will likely pivot extremely quickly to the shortstop market. Here’s where I would say I hope therefore that the Yankees do retain Judge, but the reality is that the Giants are at least as big of a threat to land a shortstop if they don’t get Judge. So it might not matter.
  • Ken Rosenthal reports that, despite how whacky it seems, the Padres really are in the shortstop market. The idea is that they would add a top shortstop like Trea Turner, move Ha-Seong Kim to second base, move Jake Cronenworth to first base, and move Fernando Tatis Jr. to the outfield.
  • Also from Rosenthal, he writes that even if the Dodgers don’t retain Turner, they might still pursue one of the other top three shortstops – albeit on their terms, which is presumably shorter-term, higher-AAV.
  • Elsewhere in annoying teams that are crowding the shortstop market, Jon Heyman reports that the Orioles are involved, too. That said, he doesn’t sound optimistic that they actually land one of the four.
  • Kiley McDaniel breaks down Trea Turner’s market from a price tag perspective, and although he’d projected an eight-year, $272 million deal, McDaniel lays out how it’s possible Turner could wind up topping $300 million.

Are the Cubs willing to spend big to land a superstar shortstop?

That is the question on the collective minds of Cubs fans right now. The North Siders are not one piece away from being a legitimate contender, but the club looks to be on the rise with prospect talent climbing up the system. The division is winnable, the team has both spending power and flexibility and there are four big-name free-agent shortstops available. Landing one might require stepping outside a comfort zone (both in cost and contract length), but star power is something the Cubs need as they try to regain their footing for a run at an October berth.

  • I like when the team website has a discussion of how the Cubs should totally be signing one of these guys. I’m not saying that means anything special, just that it means even Bastian sees – and is willing to say – that it’s pretty obvious the Cubs need to land one of these guys right now.

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Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.