Having a window to win a championship is a very fragile thing in MLB.
When the opportunity to win a title comes along, you better go all in and seize your chance.
That’s the philosophy that many sports executives live by.
But all choices have consequences, and when a team’s window closes with no title to write home about, organizations are left picking up the pieces after going all in.
A couple of MLB teams may find themselves in a similar position after the 2021 season.
These two clubs likely regret trying to compete this year.
2. Minnesota Twins
The Minnesota Twins were widely regarded as the favorites to win the American League Central division before the season started.
That has not gone to plan.
With nearly three months gone in the 2021 MLB campaign, the Twins’ 31-42 record is the worst mark in the AL Central.
The Twins spent around $40 million in free agency in hopes of building a contending team.
The team also added Kenta Maeda via trade prior to the 2020 season in hopes of bolstering its rotation.
Unfortunately, many of those moves have not panned out.
Aside from Cruz (who has a stellar .306/.380/.572 slash line) and Robles (who has a 3.48 ERA over 34 appearances), all of the other investments have struggled.
Simmons has a .630 OPS, Happ has a 6.09 ERA, Colome has a 5.40 ERA, Shoemaker has a 7.31 ERA, and Maeda has a 4.85 ERA.
Watching J.A. Happ pitch is torture and no one should ever have to endure it. #MNTwins
— Adam Hentges (@Ah3ntg3s) June 22, 2021
Starting pitching has been the fatal flaw, as the club’s 5.00 rotation ERA ranks 26th in all of MLB.
To make matters worse, the Twins will likely lose some crucial players in free agency in the offseason—the aforementioned Cruz, Robles, and also Michael Pineda, who has been one of Minnesota’s very few reliable starting pitchers in recent years.
1. Chicago Cubs
The Chicago Cubs are on this list for a different reason altogether.
No team will ever be upset about contending, but in a year or two, the Cubs organization and its fans may wish that this 2021 club played like a losing team from the gate.
Here is why.
The Cubs are set to lose a plethora of talent to free agency this offseason.
The club will likely be unrecognizable next year.
There is so much trade value in that group that it’s hard to even fathom the potential haul that the Cubs could get.
But Chicago isn’t in a position where a deadline sell would make a whole lot of sense.
Because the team has blown preseason expectations out of the water and is currently just half a game back of the first-place Milwaukee Brewers.
The Cubs aren’t on this list because the organization went all in on 2021 knowing that the team’s window is about to close—they’re on this list because the team is playing some inspired baseball, which oddly might end up costing the franchise in the long run.
If Chicago falls short of the ultimate goal of a World Series title, then the core will be dismantled in free agency, and the organization will regret not flipping those expiring deals into some young talent.
The Cubs could technically still punt on the 2021 season and sell at the deadline, but throwing away a shot at a title feels wrong.
— Tommy Gahan (@GahanTommy) May 27, 2021
Whether it’s what the organization wanted or not, the Cubs are firmly in the mix this season, and not by design.