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2 MLB offseason mistakes that will haunt the Chicago Cubs

The Cubs did enough this winter to improve the roster, but some big holes put a real ceiling on what this team can accomplish.
Los Angeles Dodgers v Chicago Cubs: MLB Tokyo Series
Los Angeles Dodgers v Chicago Cubs: MLB Tokyo Series | Masterpress/GettyImages

The Chicago Cubs have opened the season 1-2 after a 10-run outburst during their domestic Opening Day in Arizona. The Cubs look to have an improved team from a season ago but are also missing a couple of critical pieces on their roster that will hinder them from being a serious contender. Let's take a look back at two offseason mistakes that will come back to haunt this team.

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1. Not matching the Dodgers' offer for Tanner Scott

The Chicago Cubs were near the top of the board in blown saves in 2024. It was a big reason they fell to an 83-win season, as opposed to being in the upper 90s with the Wild Card teams that were fighting for a Postseason spot. Over this past winter, the Cubs looked to address that hole by adding Tanner Scott, the premier closer in the free agent market. Ultimately, the Cubs offered three years, and the Dodgers beat their offer with a four-year contract.

The part that stung the most was that Tanner Scott wanted to play for the Cubs but took the extra money to be with a perennial World Series-caliber team. Who could blame him? Nobody should leave millions on the table, and this was a failed execution from the Cubs front office, which has increasingly become hopeful to sell players on shorter deals with the "Wrigley Field" experience, the way they wooed Shota Imanaga, as well as trying to get guys like Alex Bregman. Not ponying up and just paying the guy has been the Cubs' downfall in recent seasons, ever-holding them back from being a true competitor.

2. Not signing a better starting pitcher

After the Cubs shocked the world by trading for Kyle Tucker, it made sense that a Cody Bellinger trade was inevitable. The belief in Chicago was that those funds saved on Bellinger's contract would be reallocated to enhance the starting rotation, who had only added a reclamation project in Matt Boyd, who showed signs of life at the end of 2024 after coming back from an injury. With multiple names to choose from, the Cubs decided not to spend that money and instead roll with what they have, hoping one of their depth pieces will step up and make a difference.

The catalyst for this was not Jed Hoyer but owner Tom Ricketts, whose cries of breaking even are begged to differ by Forbes' list of most valuable franchises, indicating the Cubs' current worth at $4.6B, up from the $4.22B in 2024.

Because of penalties that come with exceeding the luxury tax, the Cubs refuse to go over that first tier on purpose, but the fact is, this season, they are still $25 million under the luxury tax. They have no reason they couldn't have paid up for either Tanner Scott, Bregmn, or more importantly, a top-tier starting pitcher more capable of bringing something to the table than what the team hopes Matt Boyd can bring.