5 stories to watch for during the MLB Winter Meetings

There’s going to be one team that makes a head-scratching move

The Winter Meetings should help identify the direction of plenty of teams, and while so many clubs are saying they’re looking to improve or compete in 2020, there will be teams that will see the writing on the wall and might switch directions.

The most obvious of those teams are the Cubs, who have confirmed they will consider all moves this offseason, including trading core pieces like third baseman Kris Bryant or catcher Willson Contreras.

And while President of Baseball Operations Theo Epstein has said the Cubs plan on remaining competitive in 2020 and beyond,  Ken Rosenthal reported last week that the Cubs were telling “low-budget free agents” they need to clear money before they can start to negotiate. If that is truly the case, the Cubs may have to trade a player like Bryant or Contreras (or both) before any major signings can happen.

Another team in a strange situation is the Los Angeles Dodgers, who have tons of space on their books after 2021, and can take on a big-time commitment. And after coming so close the last few years to winning their first championship since 1988, the Dodgers are in a prime position to make a move.

That being said, Dodgers General Manager Andrew Friedman has historically not paid top-dollar for top free agents. But after five first-place finishes in the past five seasons with no World Series rings, Friedman may take advantage of the financial flexibility his club has and sign one of the top arms on the market. A rotation that has been built around future Hall of Famer Clayton Kershaw over the last decade needs some new faces.

Plus, with Hyun-Jin Ryu likely leaving in free agency this season and veteran third baseman Justin Turner starting to show signs of regression, adding a player like Rendon or Cole would make the Dodgers the clear favorites in the National League for the foreseeable future. But even a starter like Madison Bumgarner would be a big surprise, as Ken Rosenthal teased in his most recent story for the Athletic, who has infamously not gotten along with this current Dodgers group.

There’s plenty more to be excited about as the MLB Winter Meetings look to officially kick-off 2019 Free Agency as teams dream of finding that one piece that pushes them to the top in 2020.