Cubs: What would it take for Adam Wainwright to come to Chicago?

Adam Wainwright, who has spent his whole career in St. Louis, could help the Cubs in 2021.

The Chicago Cubs are likely going to be looking for some starting pitching help this offseason with the departure of Jon Lester, Jose Quintana and Tyler Chatwood. Adbert Alzolay could be a solution for the rotation, but it still would be nice to get some help from outside the organization. And as always, there are a lot of free agent possibilities.

One interesting name to throw out there is Adam Wainwright, who has been with the St. Louis Cardinals since his major league debut all the way back in 2005. Wainwright, who will be 40 during next season, has made 326 career starts, owns 167 wins, has a lifetime ERA of 3.38 and has finished in the top three in NL Cy Young Award voting four times.

I probably don’t need to tell Cubs fans much more about what Wainwright has done throughout his career, as he’s made 51 career appearances against the Cubs and has pitched more innings against them than he has against any other team. Lifetime, the big right-hander owns a 17-13 record with a 4.12 ERA against the Cardinals’ rival from the north.

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A lot of Cubs fans may balk at the thought of Wainwright coming to Chicago for a couple of reasons: first, because of his history with the team’s hated rivals; and second, because of his age. However, Wainwright quietly had a nice season with St. Louis in 2020, making ten starts which included two complete games. He posted a 3.15 ERA overall and didn’t give up more than three runs in any start, while he made it through at least five innings every time.

In addition, if the front office is looking for veteran leadership – perhaps it will be missed with the departure of Lester – then Wainwright would seem to fit that bill.

Wainwright isn’t the first former Cardinal to come up on these pages, as Kolten Wong recently became a free agent and could be a solution at second base. Another question is whether Yadier Molina and Wainwright are a package deal; after all, they’ve been together in St. Louis for so long.

The Cubs are set at catcher, so they’re likely not interested in Molina. And besides, if indeed Molina and/or Wainwright leave their longtime home in St. Louis, it would be hard to pull that off for another team (though the Cubs managed to with Lester and David Ross a few years back).

I don’t know how likely it is that there would be interest from either side between Adam Wainwright and the Chicago Cubs. However, if the team is looking for a veteran pitcher they wouldn’t have to commit much money to, Wainwright could be a good fit.