Have the Chicago Cubs finally remembered that they’re the Chicago Cubs? -

This offseason the Chicago Cubs have re-entered the World Series conversation for the first time since winning it all back in 2016.

By trading for Edward Cabrera and signing Alex Bregman, Jed Hoyer fleshed out a roster that went 92-70 last season before losing 3-2 to the Milwaukee Brewers in the NL Division Series.

Although All-Star outfielder Kyle Tucker opted not to re-up with the team (or the Cubs opted not to bring him back), the vibes at Wrigley Field are pretty high right now, not least because the Cubs actually paid a big name free agent for the first time since signing Dansby Swanson back in 2022.

Bregman’s contract became the third largest in franchise history, behind only Swanson’s and the mega deal Jason Heyward signed in the winter of 2015:

The Cubs did make a cursory offer to Bregman last offseason. Although, as Hoyer expressed in a fiery interview back in February, it wasn’t enough to snag the All-Star third baseman, who, of course, ended up signing with the Boston Red Sox.

A year on, it’s probably safe to assume that Chairman Tom Ricketts wanted Hoyer to prove that the Cubs could compete before spending that kind of money on another free agent.

If you’re feeling generous this kind of makes sense, given that prior to last year the Cubs hadn’t made the postseason proper since 2017. If you’re not, why give up such a large haul for a year of Kyle Tucker if you’re not going to go all in, you might ask?

Given the start they made last year – they were 57-39 at the All-Star break – one has to wonder what the Cubs could have achieved with a bat like Bregman’s in their line-up. After all, they had to rely on rookie Matt Shaw at third – he hit .226 / .295 / .394 with a .690 OPS – while also navigating some slightly bizarre territory with Tucker’s fractured hand, strained left calf and Craig Counsell-imposed ‘mental rest’ break.

It all resulted in a difficult second half that saw the Cubs go 35-31 after the All-Star break while finishing second in the NL Central to the Brewers for the third year in a row.

Ironically, the real issue when the postseason rolled around was actually their starting pitching. In the absence of Justin Steele, who underwent left elbow surgery in April, and with Shota Imanaga struggling to limit home runs, the Cubs had to rely on the aging and by all accounts exhausted remnants of their rotation, particularly after rookie Cade Horton went down with a rib injury prior to the NLDS.

Matthew Boyd, Jameson Taillon and Colin Rea did what they could and, to be fair to the Cubs, they pushed the Brewers all the way in that series, but the overriding feeling was that they were ultimately one or two pieces short. Not least after watching Boyd and Imanaga get shelled in the first two games:

Had the Cubs behaved like a team that was truly serious about winning at the trade deadline, who knows what might have happened. Surely they would have put up more of a fight against the L.A. Dodgers in the NLCS than the Brewers – who were swept in four games – did had they acquired more than Michael Soroka, Andrew Kittredge, Taylor Rogers and Willi Castro at the deadline.

They were linked to the likes of Mitch Keller, MacKenzie Gore, Sandy Alcantara and Cabrera himself, although, again, they were reluctant to go all in when it came to the punch. And it’s hard to dispute the fact that their frugality, both before and during the season, ultimately cost them.

Cabrera, who went 8-7 with a 3.53 ERA last season for the Marlins, represents a huge upgrade to this rotation, particularly when it comes to missing bats, provided he can stay healthy.

Speaking at CubsCon this weekend, Counsell said: “We see Edward as a pitcher who’s just ready to take off. He’s off to a great start in his career and [has a] lot of big things ahead. We have to figure out how to get him to the next place.”

If the Cubs can keep him healthy, while also using their vaunted pitch lab to help him develop, they might realistically have one of the best rotations in baseball next season; one that can hopefully stand up to the rigours of the postseason, should they make it back there.

That’s why this offseason feels so refreshing; because the Cubs are finally behaving like a team that was named MLB’s fourth most valuable by Forbes heading into the 2025 season.

And while no one can realistically hope to compete with the Dodgers – who added Tucker to their already stacked roster last week – on paper, the Toronto Blue Jays proved that they might not be truly infallible in an incredibly entertaining World Series that went down to the wire.

By adding Cabrera and Bregman, while also rebuilding the bullpen, Cubs brass have proved that they’re willing to make the most of this competitive window. And, arguably, due to the lack of movement we’ve seen from the likes of the Brewers and Philadelphia Phillies so far this offseason, they may be considered by some the second best team in the National League when the next round of power rankings are published.

After a decade of diminishing returns and confounding frugality, it finally feels like the Chicago Cubs have remembered they’re the Chicago Cubs.

Here’s hoping they don’t go and spoil it all by trading Nico Hoerner for luxury tax purposes.

Sean Guest is Bat Flips and Nerds’ Chicago Cubs contributor. He can be found on Twitter @ThatLondonCub.

Image credit: Matt Dirksen/Chicago Cubs/Getty Images