Imagine waking up to news that your favorite baseball team came oh-so-close to landing a superstar hitter, only to watch him sign with a rival for a massive payday. It's the kind of heartbreak that keeps sports fans up at night, wondering 'what if?' But here's where it gets controversial: are these 'close calls' just smoke and mirrors from teams trying to save face, or genuine glimpses into smarter strategies? Stick around, because we're diving deep into the Chicago Cubs' latest offseason whispers, and trust me, this is the part most people miss—the untold stories behind the deals that slipped away.
First off, let's break down the buzz around Pete Alonso, that power-hitting first baseman who's now locked in with the Baltimore Orioles on a whopping five-year, $155 million contract. These kinds of rumors can spark endless debates: some fans see them as clues to a team's true intentions, while others dismiss them as mere public relations stunts to appease disappointed supporters. Personally, I lean toward the middle ground—it's fascinating to hear that the Cubs reportedly had an in-person meeting with Alonso just days before his big signing. According to MLB insider Jon Heyman, this sit-down happened during the Winter Meetings in Orlando, Florida, alongside the Boston Red Sox. For newcomers to baseball talk, the Winter Meetings are like an annual trade show where teams huddle to discuss deals, sign players, and swap talent—it's a high-stakes networking event that sets the tone for the season.
Now, does this meeting even count now that Alonso's happily inked with Baltimore? Not really, in terms of immediate impact, but it does fuel the idea that the Cubs are actively scouting for a game-changing slugger this winter. With star outfielder Kyle Tucker likely heading elsewhere (perhaps to another contender), the Cubs' interest in Alonso highlights their desire to boost their lineup. Heyman noted that Alonso snuck in through a side entrance and service elevator to avoid the media spotlight—classic stealth mode for big-league negotiations. No specific offers were mentioned from the Cubs or Red Sox, so it's more of a 'we explored the option' than a near-miss.
And this is the part most people miss: tying it all together, there's another layer to this saga. Veteran reporter Robert Murray revealed that the Cubs also held a Zoom call with Alex Bregman a few weeks back. Bregman, a versatile infielder and hitter known for his clutch performances, could be a solid addition if the Cubs decide to pivot. But here's where it gets interesting—and a bit controversial. I don't expect the Cubs to suddenly splash cash on multiple big-name free agents, but if they're testing the waters with these bats, it might signal a focus on trades for top pitching talent. Think about it: instead of overpaying for pitchers like Tatsuya Imai or Michael King, why not trade for rising stars like MacKenzie Gore or Edward Cabrera, both young fireballers with high potential? Pair that with bringing in Bregman for his steady offense, and suddenly the Cubs look like a team playing smart chess rather than reckless checkers. Of course, this sparks debate: is trading for prospects the wiser long-term move, or should the Cubs go all-in on proven free agents to compete now?
Shifting gears to another 'almost' moment that hits closer to home—this one stings a little more for Cubs faithful. As reported by Bruce Levine, free agent closer Devin Williams actually preferred signing with Chicago over the New York Mets. All things being equal, Williams would've chosen the Cubs' vibe and history (that iconic ivy on the walls at Wrigley Field can be a siren call for players). But reality bit hard: the Cubs' three-year offer fell short of the Mets' $51 million deal. It's a classic case of money talking louder than loyalty, and for baseball beginners, a 'closer' is the pitcher who seals wins in the ninth inning, often earning high praise (or blame) for their clutch saves.
Yet, sometimes these misses turn into blessings in disguise. Consider last offseason, when the Cubs finished second to the Los Angeles Dodgers in the race for closer Tanner Scott. Scott had a rough 2025 season in LA, posting a 4.74 ERA (earned run average—a stat measuring how many runs a pitcher allows per game, where lower is better), racking up 10 blown saves (those game-losing moments when the closer fails to protect a lead), and dealing with two injury stints that sidelined him for the playoffs. Not every signing pans out, as Scott's struggles prove—sometimes, the player who got away becomes the one you dodged a bullet on. Obviously, teams aim for stars who deliver, but it's a reminder that scouting isn't a perfect science.
Looking back, since the offseason kicked off, the Cubs have been linked to several big names who ultimately signed elsewhere: Dylan Cease (that electric pitcher now with another team), Emilio Pagan (a reliable reliever), Pete Alonso, and now Devin Williams. It's a pattern that begs the question: are the Cubs being too cautious with their wallet, or are they building patiently for the future?
Do you agree that these 'almost' stories are just lip service from the Cubs, or do they reveal a team that's strategically positioning itself? Is trading for young pitchers over signing free agents the right path—and what about Williams? Should the Cubs have matched the Mets' offer despite the risk? Share your hot takes in the comments; I'd love to hear if you're Team Trade or Team Big Spend!
