Could Chicago Cubs Historic Free Agent Flop Be Making Ownership Hesitant to Spend?

The Chicago Cubs made a historic commitment to a free agent in 2016 that turned out to be a disappointment.

Jun 22, 2022; Pittsburgh, Pennsylvania, USA; Chicago Cubs right fielder Jason Heyward (22) in the on-deck circle against the Pittsburgh Pirates during the seventh inning at PNC Park. / Charles LeClaire-Imagn Images

Early in the MLB offseason, it was reported the Chicago Cubs would not be major players in free agency as ownership wasn’t going to open up their checkbook.

To this point, they have stayed true to that word.

The largest contract handed out by the team was to starting pitcher Matthew Boyd, formerly of the Cleveland Guardians, who agreed to a two-year, $29 million deal. Catcher Carson Kelly also agreed to a two-year deal with the team priced at $11.5 million.

While it is certainly disappointing to see a big market club not spend like other franchises in similar situations, the Cubs did make a huge move on the trade market, acquiring Kyle Tucker from the Houston Astros.

Shortly after that deal was completed, the team shipped former MVP Cody Bellinger to the New York Yankees in exchange for pitcher Cody Poteet in what was nothing more than a salary dump.

Fans would love to see some of the money saved from moving the slugging lefty redistributed elsewhere on the roster.

The bullpen could use some help, and the Cubs are reportedly still in the running for Roki Sasaki.

But, it is certainly frustrating to see a front office working with such tight restraints when there is money that can be spent.

Could some of ownership’s hesitancy in spending be because of past moves that didn’t pan out?

That could certainly play a part, as Chicago did agree to one of the largest free-agent contacts in MLB history in 2016 when they signed outfielder Jason Heyward to an eight-year, $184 million deal to become a cornerstone piece of the puzzle.

He was only 26 years old when he hit free agency and had already recorded four seasons with a WAR of at least 5.5.

Unfortunately for the Cubs, that level of production never arrived at Wrigley Field.

Joel Reuter of Bleacher Report gave the deal a “D” grade, with only one saving grace keeping it from being an “F”; the speech he delivered during the rain delay of Game 7 against the Cleveland Indians.

Aiding in winning a title and two Gold Glove Awards in his first two seasons in the Windy City are what Heyward has to show for one of the largest contracts ever seen in baseball history.

Ending that championship drought was worth any amount of money to the franchise, but they would have certainly liked to see a more positive return on their investment.

An 87 OPS+ and 8.9 WAR across seven seasons is tough to put a positive spin on, even with the World Series victory.

It is a move that could very well be haunting the team to this day.

Even owners with seemingly endless supplies of money will get gun-shy if too many moves don't pan out well.

Heyward's massive contract, which the team ended up eating $22 million of in the last year to move on from, could certainly play a part in their hesitancy to jump back into the free-agent market.

Alas, if the Cubs want to return to the top of the NL, their spending habits need to change.

They are on the cusp of building something special with the amount of talent they have coming through the prospect pipeline, so augmenting that group with established veterans is the fastest way to return to prominence.

Spending whatever it takes to retain Tucker long-term would be a great step in the right direction for the franchise looking to gain some goodwill and trust back from the fan base.