Cubs: Three controllable starting pitchers to trade for

Jon Lester is entering his final year with the Chicago Cubs in 2020. The front office needs to consider long-term plans for the rotation.

It’s difficult to imagine that Jon Lester‘s contract will expire at the end of next season. When the then 31-year-old pitcher agreed to sign with a rebuilding Chicago Cubs team, the decision left many wondering if Lester was chasing a paycheck. After all, he had just won two World Series championships with the Boston Red Sox and departed in free agency for a Cubs team loaded with potential, but unproven prospects.

Flash forward five years and one historic World Series later, Lester looks like the best free-agent signing in franchise history. His regression in the second half of last season was expected, and surprising to most that it didn’t happen sooner. As noted, the now 35-year-old will be a free agent after the 2020 season, and the Cubs rotation looks weak outside of Yu Darvish and Kyle Hendricks. Jose Quintana and Tyler Chatwood will be free agents as well after the 2020 season, and neither is likely to return.

The Cubs have done a better job of developing pitchers within their organization, but outside of Brailyn Marquez, there is not a clearly defined pitcher ready to be inserted into the 2021 rotation with the potential to become a quality starter. Adbert Alzolay is looking more like a bullpen arm, Tyson Miller had an impressive stint at Triple-A Iowa, and it’s too early to decide on the likes of Cory Abbott, Riley Thompson, Justin Steele, and Ryan Jensen.

Perhaps a name not mentioned above with emerge from the pack, but Theo Epstein should be on the phone to acquire one or two controllable starting pitchers.

Kyle Freeland, LHP (Rockies)

Under team control through the 2023 season, the 26-year-old southpaw had a difficult 2019 season, posting a 6.73 ERA in 22 starts. Combined with injuries and a demotion, it was not how he envisioned the season to unfold, especially considering he finished fourth in the Cy Young voting in 2018. A closer review of his pitching splits from last season indicates that he was the victim of Coors Field’s reputation, posting a 9.25 ERA compared to 4.61 on the road.

His 1.80 ERA in September was encouraging heading into the offseason, and his value will likely never be lower. A return of infielder Aramis Ademan and Abbott should get the deal done and wouldn’t impact the Cubs’ long-term plans.

Chris Bassitt, RHP (Athletics)

Formerly a 16th round pick by the White Sox, Bassitt has quietly emerged as a useful starting pitcher with the Oakland Athletics. In his last three-of-four seasons, the 30-year-old righty has posted sub-4.00 ERA year, including 25 starts last year. He’s under contract through the 2022 season and will make just $2.8 million in arbitration this offseason. His sinker and four-seam fastball have terrific late tailing action and complement those with a devastating curveball.

The Athletics will open the season with an $86 million payroll, which deviates from their standard practice. Accompanied by the fact that they have both Jesus Luzardo and A.J. Puk projected to be inserted into the starting rotation soon, Bassitt could be an expendable piece that the Cubs should hop on. The outfield remains crowded on the north side of Chicago, and a return of Brennan Davis should easily get this deal done.

Sandy Alcantara, RHP (Marlins)

Alcantara had a breakout year with the Marlins in 2019, posting a 3.88 ERA in 32 starts. It was his first full season in the rotation and earned an All-Star selection for his efforts. The 24-year-old is under team control through the 2023 season, and would likely be the most difficult to acquire. However, the Marlins essentially gave away Christian Yelich, so who honestly knows.

Alcantara would easily slide into the rotation this season as the team’s fifth starter with the likelihood of being after both Darvish and Hendricks in 2021. He displays excellent velocity on his primary pitch, a four-seam fastball that tops in the high 90s while producing an opponents’ batting average of just .229 last year. Alcantara complements it with a terrific curveball that produced an absurd .184 batting average.

The Marlins lost talent at the catching position when they dealt J.T. Realmuto and don’t have an immediate successor. Miguel Amaya and Ryan Jensen would be a fair trade, giving the Marlins a catching prospect and a starting pitcher prospect when they are ready to be competitive again.

(All trade values determined from BaseballTradeValues.com)