Chaos or Chess? MLB Braces for One of the Wildest Trade Deadlines in Years, and Tim Kurkjian Says “We’ve Never Seen Anything Quite Like This”
By [ JOYCEDUONG ] | June 30, 2025
As the calendar flips toward July and baseball’s midsummer heat reaches a boil, there’s one thing every front office, player, and fan across Major League Baseball seems to agree on: this year’s trade deadline could be absolute mayhem.
Few people have watched more trade deadlines unfold than veteran baseball analyst Tim Kurkjian. And in a recent segment on ESPN, he didn’t mince words.
“It’s a very interesting trade deadline this year,” Kurkjian said, leaning forward with that trademark grin. “We’ve got big names possibly moving, surprise contenders in the mix, and front offices under enormous pressure. I’m not sure we’ve ever seen anything quite like this.”
Kurkjian, who’s spent four decades chronicling the inner workings of MLB, rarely tosses around hyperbole. Which is why fans — and rival executives — are hanging on every rumor, every whisper, and every cryptic social media post hinting at deals in the works.
A League on Edge
There are plenty of reasons why the 2025 deadline feels more combustible than usual.
First, there’s the sheer number of star players on teams hovering around .500. Unlike in past seasons, where clear sellers and buyers were obvious by mid-June, this year’s standings have left half the league clinging to playoff hopes.
“Teams are terrified of selling too soon,” one American League executive told The Athletic. “But they’re equally terrified of standing pat and missing the postseason by three games.”
The San Diego Padres, for example, sit just two games out of the NL Wild Card — but have been rumored to be shopping outfielder Juan Soto, who becomes a free agent this winter. Meanwhile, the Toronto Blue Jays could pivot to sell mode if they don’t make up ground in the AL East, potentially dangling Bo Bichette or even Vladimir Guerrero Jr. in blockbuster talks.
High-Priced Stars, High-Stakes Decisions
Among the biggest names drawing speculation is none other than Chicago White Sox ace Dylan Cease. After years of rebuilding, the White Sox look ready to cash in on their frontline starter to restock the farm. The Dodgers, Yankees, and Orioles have all been linked to Cease in recent weeks.
And then there’s Pete Alonso. The Mets first baseman — and one of baseball’s premier power threats — is also in a contract year. While new Mets president David Stearns has insisted the team remains “focused on winning,” rival executives believe New York may quietly gauge Alonso’s market if they fall further behind in the NL East.
“This is where GMs earn their money,” Kurkjian said. “Because it’s not just about this year — it’s about whether you’re willing to trade a star and take the PR hit, or gamble that you can sign him and compete next year.”
Surprise Buyers Waiting in the Wings
What’s adding even more intrigue is the rise of unexpected contenders.
The Pittsburgh Pirates have surged into Wild Card contention, led by a breakout season from shortstop Oneil Cruz. Rumors swirl that Pittsburgh could make an uncharacteristically aggressive play for offense, possibly eyeing Red Sox slugger Rafael Devers if Boston decides to retool.
Meanwhile, the Kansas City Royals — yes, the Royals — find themselves leading the AL Central and reportedly have interest in upgrading their rotation. It’s a stunning development in a division many thought Cleveland or Minnesota would dominate.
“There are teams sniffing around guys like Corbin Burnes, Jesús Luzardo, or even Justin Verlander,” an AL scout said. “Nobody wants to blink first, but the market is going to explode once that first domino falls.”
The New Wild Card: Expanded Playoffs
One massive wrinkle in all of this chaos is MLB’s expanded playoff format. With six spots per league, more clubs believe they have a legitimate shot to sneak into October.
That has created a logjam where teams who’d normally sell are hesitant — because just a decent few weeks might change their entire outlook.
“The expanded postseason has fundamentally changed the trade deadline,” Kurkjian said. “Front offices are terrified of selling and watching their fans revolt, but they’re also wary of trading top prospects for rentals. It’s fascinating.”
Fans Eager for Fireworks
And then there’s the fan factor. Social media has transformed the deadline into a 24/7 rumor mill. Instagram and X (formerly Twitter) are flooded with mock trades, leaked flight manifests, and random photos of players at airports fueling speculation.
A single tweet from Jon Morosi or Ken Rosenthal can send fanbases spiraling into hope — or panic.
“This is the entertainment business,” Kurkjian said with a laugh. “People love trades. They love dreaming big. And they’re going to get plenty to talk about this year.”
The Final Countdown
All eyes are now on the coming month as executives weigh gut-wrenching decisions. A single deal could shift the balance of power in October — or haunt a team for years.
For now, Kurkjian remains riveted.
“I’ve been around this game a long time,” he said. “But I can honestly say this could be one of the most unpredictable deadlines we’ve ever had. Get ready for surprises.”
And if Tim Kurkjian’s instincts are right, the next few weeks might deliver the kind of drama that reminds everyone why baseball’s hot stove burns so bright — especially at the trade deadline.