5 big mistakes the Chicago Cubs have made in recent years

This past offseason has been a breath of fresh air for Chicago Cubs fans. The past few years have been painful, to say the least, with the Cubs front office shipping off some of the most popular players in recent memory including Anthony Rizzo, Kris Bryant, and Javier Baez. Each of them helped bring a World Series championship to the North Side of Chicago for the first time since 1908. Luckily the recent additions to the team seem to be signaling a change in direction, and a dedication to competing to win the NL Central Division.

But there were other moves in recent years that rubbed fans and players the wrong way other than the infamous 2021 trade deadline. Some were part of the two-year tank/ reset, and others were just head-scratchers that confuse me to this day. Let's look at five times the Cubs made huge mistakes in recent years.

1. The Yu Darvish trade

This is one of those head-scratchers I was talking about. Just two years after inking Darvish to a six-year contract, the Cubs sent him and catcher Victor Caratini to the Padres for a less-than-desirable prospect package. Although outfielder Owen Caissie has emerged to become the Cubs' number 10 prospect, the rest of the others involved in the deal have yet to show much promise in the minor league system.

Coming off a second-place finish in Cy Young voting in 2020, and with three years still on his contract, there was no reason to trade Darvish when the Cubs did other than to save money. This was around the time Tom Ricketts made his infamous "biblical losses" statement to justify cutting costs like the Darvish trade. It's a shame because what the Cubs need right now is a high-velocity, strikeout-inducing ace, which is exactly what Darvish has been for the Padres since the Cubs sent him there.

2. Not bringing back Jon Lester

Ok, this one wasn't necessarily a huge mistake, it was just classless on the Cubs' part. At the conclusion of his five-year contract with the Cubs, Jon Lester still wanted to pitch. And the Cubs told him they did not have the money to pay him. Lester wound up signing a $5 million deal with the Washington Nationals in the offseason. While there didn't seem to be any hard feelings between Jon Lester and the Cubs organization, not matching a measly $5 million contract to the ace that broke your 108-year-old World Series drought is the type of penny-pinching that rubs me the wrong way.

Although his production dipped significantly in the final years of his career, Lester deserved to retire with the Cubs. Especially because his former personal catcher and good friend David Ross was the manager. There was nothing more painful than watching Lesterget traded to, and retire with the St. Louis Cardinals.