The air in Chicago today is biting, the kind of January cold that makes you want to stay under the covers until April. But inside the Sheraton Grand, things are heating up in a way that feels like 2016 all over again. If you haven't been tracking major league baseball this week, you’ve missed the moment the 2026 season actually started.
It’s easy to think of January as the "dead zone" of the sports calendar. Football has the playoffs, and baseball is just a bunch of guys in fleece pullovers talking about "process" at fan conventions. Honestly, that’s usually true. But the last 72 hours have been absolute chaos.
The North Side Just Got Scary
Alex Bregman is a Chicago Cub. Let that sink in.
After a decade of being the heartbeat of the Houston Astros and a quick, high-priced pit stop with the Boston Red Sox, Bregman just inked a five-year, $175 million deal to man the hot corner at Wrigley Field. It’s a massive statement. The Cubs, coming off a 92-win season and a frustrating NLDS exit, aren't just "hoping" to compete anymore. They’re buying.
Bregman isn't just bringing his Gold Glove and his Silver Slugger. He’s bringing a chip on his shoulder. During his press conference on January 15, he revealed he’s switching his jersey to No. 3. Why? Because he wants a third World Series ring. Simple as that.
The Cubs didn't stop there. They’ve been working the phones like a telemarketing firm on a deadline. They traded for Edward Cabrera to anchor the rotation and snagged Phil Maton for the bullpen. Manager Craig Counsell basically told reporters at the Cubs Convention today that five playoff games last year wasn't enough. He wants three more weeks. He wants October.
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The Mets and the $126 Million Question
While Chicago is celebrating, New York is doing what New York does best: spending and debating.
The Mets just dropped $126 million to bring Bo Bichette to Queens on a three-year deal. It’s a fascinating move because Bichette is coming off a massive rebound year. In 2025, he hit .311 and looked like the superstar the Blue Jays once thought he’d be forever.
Some fans are worried. They’re asking if three years is too short or if $42 million a year is too much for a guy who had a rough 2024. But honestly, the Mets needed a jolt. With Pete Alonso now an Oriole—which still feels weird to type—the lineup needed a new focal point. Bichette provides that. He’s the kind of player who changes the geometry of a defense.
Beyond the Big Checks: The Real Stories
It’s not just about the superstars. Major league baseball is currently defined by a flurry of "under-the-radar" moves that will probably decide the division races in July.
- The Cardinals are hosting their Winter Warm-Up at Busch Stadium today. It’s a sea of red, but the mood is transitional. They just traded the legendary Nolan Arenado to the Diamondbacks for a package centered around Jack Martinez. It feels like the end of an era in St. Louis, but the fans are already gravitating toward JJ Wetherholt, the kid who looks like the future of that infield.
- The Dodgers are being the Dodgers. They just quietly added Kyle Tucker on a four-year deal and brought in Edwin Díaz to fix a bullpen that was, frankly, a mess last October. They’re spending roughly $40 million a year on two relievers (Díaz and Tanner Scott). It’s not "shrewd," but when you have the Dodgers' bank account, who cares?
- The Blue Jays found their replacement. After losing Bichette, they pivoted to Japanese star Kazuma Okamoto. They signed him to a four-year, $60 million deal. He’s a power threat who hit 15 home runs in just 270 at-bats in Japan last year. He’s a gamble, but he’s a fun one.
What’s Actually Happening Today
If you're looking for a game to watch, you’re about a month too early. Pitchers and catchers don't report until February 10th for the early arrivals.
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However, today is the peak of "Fan Fest" season.
In St. Louis, Masyn Winn is showing off his Gold Glove. In Chicago, Anthony Rizzo—who is back in the fold in a different capacity—is parading the 2016 trophy around to remind everyone of what’s possible. It’s a day of nostalgia mixed with intense scouting.
There’s also the trade market. Rumors are swirling that the Tigers might finally move Tarik Skubal. Every GM in the league has his number on speed dial. If Skubal moves, it will be the biggest trade of the winter, hands down.
Why You Should Care Now
Most casual fans wait for the World Baseball Classic or Spring Training to tune in. That's a mistake.
The 2026 season is being built right now in hotel lobbies and through encrypted text messages between agents like Scott Boras and front offices. The power balance of the National League has shifted toward Chicago and Arizona in just the last week.
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The Diamondbacks, by snagging Arenado, are telling the Dodgers they aren't scared. The Orioles, by signing Pete Alonso, are telling the Yankees the AL East still runs through Baltimore.
Real-World Insights for the 2026 Season
If you're looking to get ahead of your fantasy league or just want to sound smart at the water cooler, keep an eye on these three things:
- The Team USA Roster: Alex Bregman just confirmed he’s playing for Team USA in the upcoming World Baseball Classic. This means he’ll be in "game mode" much earlier than players who stay in camp. Watch for a hot start from him in April.
- The "Post-Alonso" Mets: Watch how the Mets use Bo Bichette. If they bat him second behind Francisco Lindor, that’s a nightmare for opposing pitchers. The "New York Speed" game is back.
- The Prospect Wave: Keep the name Sebastian Walcott in your head. The Rangers' shortstop is only 19 and already in Double-A. He’s 6'4" and looks like a created player in a video game. He might be the most exciting thing in the Texas system since A-Rod.
Major league baseball isn't in its "off" season. It's in its "chess" season. The moves made today at the Cardinals' Winter Warm-Up and the Cubs Convention are the opening gambits for a 162-game marathon.
Next Steps for Baseball Fans:
- Check your local team's Spring Training reporting dates; most pitchers and catchers report between February 10 and February 13.
- Keep an eye on the remaining "Big Three" free agents: Kyle Tucker and Cody Bellinger are still looking for long-term security.
- Look into tickets for the World Baseball Classic exhibitions starting March 3 if you're near Arizona or Florida.