Chicago Cubs: 3 free agents to sign, and 1 to avoid

SAN DIEGO, CALIFORNIA - OCTOBER 07: Masahiro Tanaka #19 of the New York Yankees. (Photo by Christian Petersen/Getty Images)
SAN DIEGO, CALIFORNIA - OCTOBER 07: Masahiro Tanaka #19 of the New York Yankees. (Photo by Christian Petersen/Getty Images) /
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Yankees free agents, Masahiro Tanaka
SAN DIEGO, CALIFORNIA – OCTOBER 07: Masahiro Tanaka #19 of the New York Yankees. (Photo by Christian Petersen/Getty Images) /

The Chicago Cubs have a pivotal offseason ahead of them

The Chicago Cubs returned to the postseason under the watchful eye of David Ross this year, but a flat out choke job against an inferior Miami Marlins team means the Cubs need to go back to the drawing board. With eight free agents likely not returning from last year’s team 2021 will loom much different on the North Side.

Theo Epstein might not want to spend a ton of money this offseason, but the Cubs could still nab one of these three quality free agents. They could ruin their offseason, however, if they sign one that has some question marks around him.

The Cubs should sign these free agents, but they need to be a bit restrained

43. Scouting Report. Pick Analysis. Masahiro Tanaka. player. SP. New York Yankees. 3

Tanaka is now a free agent after his seven-year contract with the Yankees elapsed. While he never became a superstar, Tanaka was a solid No. 2 starter for seven years, thereby justifying the payday. With two All-Star appearances, a solid history of success in the postseason, and a 3.74 ERA over the last seven seasons, Tanaka has all the makings of a top of the rotation guy, even as he is entering his age-32 season.

With Jon Lester on his way out, the Cubs need someone else to step into a featured role alongside Yu Darvish and Kyle Hendricks, and Tanaka could be that guy if his nasty splitter remains as un-hittable in Cubbie blue.

Darvish has returned to his peak Rangers form, while Hendricks’ soft-tossing remains uniquely un-hittable. If Epstein wants to eschew chasing the big fish like Trevor Bauer and Marcus Stroman, Tanaka could be right there for the taking at a discounted price. The Cubs are still in win-now mode, and Tanaka leaving the Yankees for the Cubs could be the sort of sneaky veteran move that tilts a competitive, deep NL Central in Chicago’s favor given the youth and depth in their lineup.