Cubs Free Agent Predictions

Seattle Mariners v Chicago Cubs
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General manager Theo Epstein has a lot of work to do this offseason after the Chicago Cubs missed out on the playoffs with a pedestrian (by their standards) 84-78 record.

Their roster remains one of the deepest in MLB, but changes need to materialize in order for them to take the next step. So, who will they target in free agency this offseason?

Here's what we can expect from the Cubbies this winter.

5. They Sign Howie Kendrick

World Series - Washington Nationals v Houston Astros - Game Seven
World Series - Washington Nationals v Houston Astros - Game Seven / Elsa/Getty Images

The Nationals would love to have Kendrick back in 2020, but his sensational performance this postseason suggests that he could make good money at 36 years old. Chicago sorely missed out on a veteran bat that crushes lefties and Kendrick absolutely fills that bill as he slashed .376/.421/.615 with six home runs and 28 RBI across 117 at-bats against southpaws in 2019. Look for the Cubs to sign the former All-Star this offseason.

4. They Trade Willson Contreras for Much-Needed Pitching Depth

Cincinnati Reds v Chicago Cubs
Cincinnati Reds v Chicago Cubs / Quinn Harris/Getty Images

We were genuinely stunned when it was disclosed that the Cubs were considering trading Contreras this winter, but if Epstein and Co. decide to offload the two-time All-Star, he could get a significant haul of much-needed pitching in return. It's no secret that Chicago's starting pitching staff struggled in 2019, as Kyle Hendricks logged the lowest ERA on the team with a 3.46 mark. We don't agree with the prospect of trading Contreras, but the organization should at least fill a hole if they opt to do so.

3. They Sign Dellin Betances

New York Yankees v Toronto Blue Jays
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Chicago's struggles on the mound didn't just revolve around their starting rotation. Joe Maddon's (now David Ross') bullpen was nothing short of woeful in 2019 and Craig Kimbrel failed to live up to his billing. Therefore, the Cubs could aggressively pursue Betances, whose stock has never been lower after appearing in just one game this past season thanks to injuries. Though injury prone, the right-handed flamethrower boasts one of the most lethal arsenal of pitches in the league and a change of scenery outside of the Bronx could work wonders for him. Expect Chicago to sign Betances this winter.

2. They Hang on to Nicholas Castellanos

Chicago Cubs v Milwaukee Brewers
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Castellanos was an absolute stud for the Cubs after they acquired him from the Tigers ahead of the trade deadline, and that production should see him receive a lucrative contract this offseason. Given the success the 27-year-old outfielder sustained in the Windy City -- he hit .321/.356/.646 to go with 16 home runs, 21 doubles, and 36 RBI across 212 at bats -- Chicago will absolutely be open to the idea of linking him to a permanent deal.

1. Javier Baez Signs a Lucrative Contract Extension

St Louis Cardinals  v Chicago Cubs
St Louis Cardinals v Chicago Cubs / David Banks/Getty Images

A report dropped on Friday which suggested that Chicago has already begun extension talks with Baez, and something tell us that a deal will get done well before spring training. The Cubs' braintrust clearly values Baez more than Kris Bryant and they will reward their faith in El Mago in a BIG way with a lucrative extension that will last until 2023 or beyond.