3 decisions that may haunt the Cubs for years to come

Halloween is one of my favorite times of the year. A season of goblins, ghouls and decisions that will haunt the Cubs front office for years to come. Looking in the rearview mirror and taking a glance at some of the decisions Chicago has made have definitely paid off – and then some.

For instance, moving Kris Bryant and Javier Baez has been a blessing in disguise, despite the heartache we felt at the time. Bryant landed on the IL three times this year, playing just 42 games with the Rockies, amassing just five home runs and 14 RBI.  Baez’ first season in Detroit was a total disaster, no matter how you look at it, as he slashed just .238/.278/.393 with 17 homers and 67 RBI.

The prospect haul received for Bryant and Baez, which included the likes of Pete Crow-Armstrong, Caleb Kilian and Alexander Canario speaks volumes about the work the front office did at last year’s trade deadline. But not every move has been a home run.

Let’s take a look at 3 decisions that will haunt the Cubs front office for years to come.

Cubs: 3 haunting decisions – #3: the Andrew Chafin trade

Trading Andrew Chafin at the time in 2021 seemed inevitable. The veteran left-hander was having a career year and had quite a bit of trade value. The problem is he’s just kept on rolling since the Cubs dealt him.

In the first half of 2021 with Chicago, Chafin registered a sparking 2.06 ERA out of the pen. From there, he got even better, putting up an incredible stretch that included a 1.53 ERA with Oakland. He finished 2021 with a career-best 1.83 ERA before signing with Detroit last winter. In 2022, Chafin recorded another impressive season, evidenced by a 2.86 ERA on the year. Sure, Brandon Hughes emerged as a nice lefty option this year, but Chafin would have given the Cubs that extra punch from the left side in late innings.

To make matters worse, Greg Deichmann, who was one of the two players acquired in the Chafin trade had already been designated for assignment. The Cubs also received Daniel Palencia as a hopeful starting pitching option down the road. In his first full year, Palencia recorded a 3.94 ERA between Single and High-A. It is worth mentioning Palencia did begin turning a corner in his last five starts. In those outings, he gave up five earned over 18 innings but struck out 26 in the process. An encouraging sign for Palencia as he hopes to find himself in Double-A Tennessee next year.

Palencia has upside to and has shown glimpses of maybe working out in the majors someday. However, a reoccuring theme we will visit it that the Cubs are looking to be competitive as soon as next year. Having an arm with Chafin’s production is one you can only hope to match and get lucky with in free agency now.

Cubs: 3 haunting decisions – #1: Non-tendering Kyle Schwarber

As if it were any real surprise that Kyle Schwarber landed at number one on this list, the evidence is piling up that the Cubs front office made a huge mistake non-tendering the slugging outfielder.

Schwarber has hit some absolute missiles in Wrigley Field over the years. From a moonshot in the NLDS that landed on top of the right field scoreboard, or a return from an ACL tear that had Cleveland pitchers spooked in the 2016 World Series, he left an indelible mark in Cubs lore.

Since leaving the North Side, he’s launched 78 regular season home runs. Considering he spent five weeks on the IL for a hamstring injury during a time that he was on a historic tear at the plate last summer, that number of total home runs the last two seasons could have been even higher. It just goes to show how locked in he has been from a power perspective.

In 2021, split between Washington and Boston, he recorded a .266 average, up from the .230 mark he had with the Cubs a year before. He dropped down to .218 here in 2022, but I’m going out on a limb here and guessing that contributing nearly 50 bombs and 100 RBI sort of takes away how much you really care about that.

Looking at this season, Schwarber hit a career-high and National League-leading 46 homers to go along with career-high 94 RBI during his first year with the Philadelphia Phillies. His production is a big part of the reason why the Fightin’ Phils find themselves in the World Series for the first time in more than a decade. The part that hurts the Cubs the most is that Schwarber was a free agent this past winter after already having a career year in 2021.

Not even trading him, but just non-tendering him in a blatant cost-cutting measure is one of the most painful moves we can look back on as Cubs fans – and it could haunt the team for years to come.