The largest free agent contract ever handed out by the Cubs came back in 2015, when Chicago lured All-Star outfielder Jason Heyward to the North Side in free agency with an eight-year, $184 million deal.
Jed Hoyer came close to setting a new high water mark for the franchise last winter, when signing Dansby Swanson to a seven-year, $177 million contract. If the Cubs president of baseball ops wants to bring highly-coveted Japanese right-hander Yoshinobu Yamamoto to Chicago, though, it'll take him wading into even deeper, uncharted waters.
Cubs would have to dig deep financially to land Yoshinobu Yamamoto
According to Jeff Passan at ESPN (subscription required), bidding for the 25-year-old will start at $200 million. Obviously, the Cubs have never gone to such lengths for a free agent, even one so young and decorated as Yamamoto.
Michael over at Bleacher Nation has a great breakdown on the finer details of not only Yamamoto, but all the intricacies that come with the posting system with him coming over from the NPB - and the wrinkle of a potential opt-out could play in this whole scenario.
More or less, it's the big fish circling Yamamoto ahead of his official posting - with both New York teams, Cubs, Dodgers and Red Sox singled out in reports from Passan and Jon Heyman, with a couple other teams getting passing mention. But it's not just dollars that will matter here: it's the fact that, again, given the fact he's so young, an opt-out that would allow him to cash in again ahead of his age-30 season could be a huge factor here.
The opt-out won't be what keeps the Cubs from landing Yamamoto. More likely, it feels like the length of a deal (not to mention the expected price tag), could prevent Chicago from adding him to the rotation, especially with several other major needs this offseason - in particular, when it comes to power bats.
Throw in the report Hoyer wants to add not one, but two starting pitchers this winter, and it feels even more likely they spread the wealth to deepen the rotation and lineup alike. Yamamoto feels like a lock to land either in Los Angeles or New York - but it's intriguing to at least see the Cubs regularly connected to the top of the free agent pool.