Cubs have a mixed history with big ticket free agent signings

Generally speaking, the Cubs have been fairly conservative in the pursuit of upper-echelon free agents. The biggest contract in Cubs' history is Jason Heyward's deal for eight years at $184 million. And while it wasn't perhaps catastrophic, it was close. Heyward was a good soldier and a strong defender, but his bat just didn't cut it. It seems like the signing of Heyward has left a mark on the organization.

While in Texas, they say, "Remember the Alamo!" in Chicago, they seem to say, "Remember the Heward signing!" For some context, Heyward's OPS while with the Cubs was .700 and his WAR for his seven seasons in Chicago was 8.9. However, despite his albatross of a contract, the Cubs won a championship. And apparently, Heyward was quite the orator. But he still wasn't worth $184 million.

But then there's Jon Lester

Jon Lester is the best free agent signing in Cub's history. The signing of Lester showed the Cubs were serious players in the hunt for a championship. In addition, he was an absolute horse in 2016, going 19-5 with an ERA of 2.44. He was also very strong in the 2016 post-season

Beyond a magnificent 2016 season, Lester led the NL in wins with 18 in 2018. He was a bulldog in the way he went about his business, and it showed itself in the way he improved his game. When he first came to the Cubs, he was a terrible hitter, but impoved to the point he was merely bad. And he became an excellent bunter.

Lester's trouble throwing to bases is well documented. However, he by working hard, he was able to at least mitigate the problem to some extent. Catcher, David Ross gets a huge assist for helping Lester control other teams' running game.

Alfonso Soriano proved to be disappointing

After signing Alfonso Soriano to an eight-year, $136 million contract, the Cubs expected more for their money. Soriano put up decent offensive numbers while in Chicago, with an OPS of .812. Soriano was a consistent power source while with the Cubs, twice hitting 30+ home runs. He also drove in 108 runs in 2012.

Soriano wasn't a great defender in left field, but he did get better. While Soriano may have underperformed his contact, he was still productive as a Cub.

Yu Darvish gets a grade of incomplete with the Cubs

Yu signed on with the Cubs for six years at $126 million. Darvish was traded to the Padres after only three seasons. During his time with the Cubs, he went 15-14 with an ERA of 3.60. It was thought at the time the Cubs didn't get a lot in return.

The Cubs did get Owen Cassie in the trade for Darvish. Depending on how Cassie's career progresses, Darvish's signing may turn out okay, at least indirectly.

And then there's Dansby Swanson and Seiya Suzuki

Generally speaking, Dansby Swanson's seven years at $177 million looks like a bit of an overpayment. Despite Swanson's underwhelming hitting, his glovework gives him a high floor. While it's unlikely the Swanson contract will ultimately look good, it probably won't turn out to be terrible.

While Seiya Suzuki has been mildly disappointing, he has performed fairly well. He's the best hitter on the team and has compiled an OPS of .824 in his three seasons with the Cubs. His five-year, $99.6 million dollar contract actually looks pretty good.

In summary, the Cubs' history with high dollar free agents has been okay, just limited.