Chicago Cubs fans have been feeling bright and sunny in recent days, after the trade for former Houston Astros closer Ryan Pressly.
The deal comes a little over a month after another swap with the Astros that brought the team all-star right fielder Kyle Tucker.
Along with the pair of Astros, the Cubs have also brought on left-handed rotation piece Matthew Boyd, lefty reliever Caleb Thielbar, right-handed reliever Eli Morgan, righty swing man Colin Rea, catcher Carson Kelly, and quality utility man Jon Berti.
Chicago Cubs Have Been Active, But Is It Enough?
All in all, that’s almost a third of a team brought in from the outside to push the Cubs over the hump when it comes to making the playoffs. After two postseason near-misses the last two campaigns, the Cubs had declared themselves “all in” this year, aiming for extended fall play this 2025 season.
However, in some eyes, the Cubs’ “all in” hasn’t been enough, especially considering the size of the Cubs’ market and their level of revenue generation.
MLB insider Jeff Passan, for example, calls the Cubs moves this offseason mostly “half-measures.”
Per Passan, via the Talkin’ Baseball podcast:
“Los Angeles Dodgers have shown that they are playing a full measure game and if you’re a team that’s going to go only half-measures, it’s not going to work out great for you and that’s where I think the Cubs…fall into at this point. They have had a half-measure winter, the half with the trades has been phenomenal…With the Cubs…they go out and get one of the 10 most talented players in all of baseball in Kyle Tucker.
“You got to add to that, it’s got to be more than Ryan Presley, like it has to be more than these little incremental moves, like you want to get leaps and bounds bigger, not just go sort of slightly, like you want jumps, not steps, and this was not a jump kind of winter in free agency for [the Cubs]”
Not “All In” Enough?
Arguably, the Cubs have made at least some “full measures,” aside from the Tucker trade. For example, they did reportedly make an uncharacteristic four-year, $66 million offer to free agent closer Tanner Scott before losing out to the slightly more generous Dodgers.
But, overall, it’s hard to argue with Passan’s take, especially when it comes to how the Cubs stack up against the Dodgers and how Chicago failed to even make a play for high-end free agents Juan Soto, Corbin Burnes, Blake Snell, or Max Fried.
The point made by Passan– and also expressed by others– is that a team’s desire to truly be “all in” when it comes to winning consistently is capped by the team owner’s desire to be “all in.”
Spending To Be Great Vs. Budgeting To Be Good
A prevailing thought among many teams is that they only need to be good enough to make the playoffs. Once there, anything can happen and they could very well fight their way to the World Series. So, why spend top dollar for top-shelf contracts?
Also, per Passan:
“You can still build a good, sustainably winning team with a low payroll, your margin for error is just minuscule at that point. And what these large market teams don’t seem to…embrace…is that the beauty of being a large market is that it buys you that margin for, buys you the ability to screw up on a contract or two and have dead money and have it look ugly in pursuit of something greater.”
The Cubs have definitely done more this offseason than any other team in their division. They SHOULD win the NL Central. But, then what? A roll of the dice in the playoffs and then back to shopping for budget specials after guys like Tucker and Pressly move on to more aggressive teams willing to pay top dollar for top talent.
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