Every trade deadline produces winners and losers on paper, but this year’s version left fan bases in three cities genuinely giddy and fan bases in three others staring at their phones in disbelief. Monday’s 6 p.m. ET deadline reshaped six rosters in ways that will define how their seasons are talked about for months, and the reactions from each fan base tell the story almost as well as the trades themselves.
Here is a walk through the three fan bases riding the highest after deadline day, and the three still processing what just happened to their roster.
MLB Trade Deadline Grades: The Fan Bases Celebrating
Some fan bases spent Monday afternoon refreshing their phones in dread. These three spent it refreshing in disbelief for a much better reason.
Los Angeles Dodgers Fans: They Got Skubal Without Giving Up the Future
Dodgers fans have been spoiled by star power for years now, but even by that standard, landing two-time AL Cy Young winner Tarik Skubal from the Tigers felt different. The return sent outfielder Zyhir Hope and pitching prospects River Ryan and Brady Smith to Detroit, and the reaction across Dodgers fandom was less “we won the trade” and more “how did we not have to give up more than that.” Multiple grading outlets agreed, handing Los Angeles an A+ or A largely because the front office kept its top-tier prospects intact while adding a genuine ace. The Dodgers even squeezed in a second move, bringing in left-hander Kris Bubic from the Royals for rotation depth, which only added to the sense that this front office is operating on a different level than everyone else at the deadline.
What makes this one fun for the fan base heading into the stretch run is the complete lack of downside. There is no “but they gave up X” caveat that usually comes with a blockbuster like this. It is a rare, clean addition of a top-of-the-rotation arm, and Dodgers fans know it.
Chicago Cubs Fans: A Complete Rotation Makeover
If the Dodgers’ deadline was about adding one name everyone recognizes, the Cubs’ deadline was about fan bases needing a scorecard to keep track of everyone who came in. Chicago added starter Kevin Gausman from the Blue Jays, right-hander Clay Holmes, starter Braxton Garrett from the Marlins, and reliever Ryan Zeferjahn — four separate additions that together represent one of the largest overhauls any team pulled off. Several grading outlets specifically called out the Cubs for adding more total value than any other team at the deadline, even after sending out shortstop prospect Jefferson Rojas and catcher Moises Ballesteros as part of the return packages.
For a fan base that has watched division races slip away in recent Augusts, seeing the front office attack both the rotation and the bullpen in the same 48-hour window is the kind of aggressive, all-in approach that turns a “we’ll see” fan base into a genuinely excited one. The Cubs’ World Series odds jumping from 20/1 on Sunday to 15/1 by Monday — the biggest single-day odds move of the entire deadline — is the market confirming what Cubs fans were already feeling.
Boston Red Sox Fans: The Shocking Catcher Trade Capped an Unbelievable Month
No fan base had a wilder deadline day than Boston’s. The Red Sox pulled off what is being described as one of the most surprising trades of the entire deadline, landing star catcher Adley Rutschman from the Orioles in exchange for a package built around top pitching and catching prospects, including Anthony Eyanson, Kyson Witherspoon, and outfielder Enddy Azocar. Boston did not stop there — reliever Erik Miller, outfielder Eli White, and third baseman Curtis Mead (acquired from the Rays for left-hander Connelly Early) also joined the roster before the deadline hit.
Context matters here. This is a team that just went 21-4 in July, arguably the best month any club has put together this season, and the front office responded to that heater by adding a top-tier everyday catcher rather than sitting on its hands. For a fan base that has ridden every emotion imaginable through a red-hot summer, watching the front office match that energy with an aggressive, multi-piece deadline is exactly the kind of moment that turns a good season into a genuinely special one.
MLB Trade Deadline Grades: The Fan Bases Still Processing It
Not every fan base got to enjoy Monday afternoon. These three are still working through what their front office just did — or failed to do.
Milwaukee Brewers Fans: So Close to the Big One
Brewers fans reportedly watched their front office pursue Tarik Skubal, the same pitcher who ended up in Los Angeles, and come away instead with right-hander Dustin May, reliever JoJo Romero, and reliever Antonio Senzatela from the Cardinals. Those are useful, real additions — but after being connected to the biggest name on the board, settling for bullpen and depth pieces is a tough landing for a fan base that had itself talked into something bigger. ESPN singled out Milwaukee as one of the deadline’s biggest losers for that exact reason.
The strange twist for Brewers fans is that the season outlook has not collapsed the way the grade might suggest. Milwaukee still carries the third-best World Series odds in the sport, which means the roster as constructed is still very much in the mix — it is just going to have to get there without the ace many fans were hoping for.
Detroit Tigers Fans: Watching Their Ace Leave Is a Tough Pill
No single storyline hit a fan base harder than Tigers fans watching Tarik Skubal, a two-time Cy Young winner, head to Los Angeles. The return of outfielder Zyhir Hope and pitching prospects River Ryan and Brady Smith earned Detroit a respectable grade from most outlets — somewhere between A- and B+ depending on who is grading — but respectable prospect grades do not fully soften the blow of losing the best pitcher on the roster in the middle of a season. ESPN named the Tigers the other big loser of deadline day, and it is easy to see why from a fan’s seat: even a good return for an ace still means watching that ace pitch for someone else in October.
The road back for Detroit fans runs through those three prospects actually developing, which is the classic rebuild trade-off — hope for 2028 in exchange for pain right now.
Chicago White Sox Fans: The Deadline’s Lowest Grade
The White Sox brought in right-hander Luis Castillo from the Mariners, sending back reliever Seranthony Dominguez, infielder Nolan Jones, and catcher/outfielder prospect Boston Smith. The reaction from grading outlets was blunt — The Athletic handed this deal a D grade, pointing directly at Castillo’s recent 5.06 ERA as a red flag on the return value. Compare that to the B+ Seattle received for making the trade, and it is not hard to see why White Sox fans are the group with the least to celebrate this week.
For a fan base already bracing for a long season, a low-graded deadline addition is not the shot of optimism most were hoping for heading into August.
What Fans in Every City Should Watch Next
The gap between these six fan bases says a lot about where each franchise believes it stands right now. Los Angeles, Chicago’s North Side, and Boston all made aggressive, multi-piece additions that fit a roster already built to win now — and all three fan bases can point to specific reasons their front office nailed it. Milwaukee, Detroit, and Chicago’s South Side each walked away with a version of “it could have gone better,” whether that meant missing on the top target, losing a true ace, or handing out a grade nobody wants attached to their team.
For fans following the stretch run and thinking about how these moves play out in October, keeping an eye on Live MLB Odds is the easiest way to track how the market reacts as each of these six teams plays out the string. And for anyone looking to put a little extra behind their read on how the deadline shakes out, checking a DraftKings Promo Code or Fanatics Sportsbook Promo Code offer is worth doing before locking in a pick. The MLB World Series futures board has already started moving on all six of these stories, and it will keep moving as the results start rolling in.
