Three Winners of the 2026 MLB Trade Deadline

There has been tons of excitement during this MLB season, and now that the August 3rd trade deadline has passed, it only gets better from here. Now, teams will be fighting for a spot in October baseball, refreshed and reloaded.

Everyone is fighting for a spot to play October baseball, and to give teams that extra push, the MLB trade deadline gives teams the opportunity to reload on talent that will help them push toward the postseason.  For teams selling, like the New York Mets, selling at the trade deadline helps the Mets because selling veteran players leads to retooling their farm system and loading up on young talent.  Buying at the deadline signals that a team is all in on making a run to the postseason; a team like the Los Angeles Dodgers trading for a CY Young Award-winning pitcher in Tarik Skubal tells you all you need to know.

Some teams will have improved their rosters, while others will disappoint.  Some teams will stay put with their roster when, in reality, they need to make some trades to keep it competitive; then you have some who traded for the wrong players or gave up too much.  There have been some interesting trades, and a lot of teams have come out on top. Let’s take a look at three winners of the 2026 MLB Trade Deadline.  

Winners of the 2026 MLB Trade Deadline

Los Angeles Dodgers

On Saturday night, August 1st, the Dodgers and the Detroit Tigers finalized a trade in which the Dodgers acquired Skubal and sent minor league prospects outfielder Zyhir Hope, right-hander River Ryan, and right-hander Brady Smith.  

There’s reason to believe that a lockout is inevitable at this point as the Dodgers trading for Skubal almost certainly solidifies it.  Of course, the Dodgers don’t care because when they have an opportunity to trade for a Cy Young Award-winning pitcher in Skubal, they’re going to jump on it.  Now, considering all the moves that the Dodgers have made over the past few years, is this fair to all the smaller-market teams? No, but again, that’s for a separate article. 

Trading a star pitcher like Tarik Skubal hurts the Detroit Tigers and their fan base, as Skubal was their undisputed ace and anchor of the franchise, but due to failed contract negotiations and free agency looming, a trade seemed more likely.  The Dodgers came calling and were aggressive enough to make a move. 

Trading for Skubal only cements their odds of winning the World Series this year.  With limited pitching on the market, Skubal was the only true difference-maker, and President of Baseball Operations Andrew Friedman treated Skubal as an “All-in” target.  Skubal only stacks up against a rotation headlined by Yoshinobu Yamamoto, Shohei Ohtani, and recovering arms like Blake Snell and Tyler Glasnow.

The Dodgers did trade two top-100 overall prospects in Hope and Ryan, along with pitching prospect Smith, but this rental could help propel the Dodgers to a third consecutive championship.  If all goes well, Skubal could be in line for an extension with the Dodgers, though this is likely a rental.

Chicago Cubs

It’s been a strong season for the Chicago Cubs as they currently stand at 63-49 and in second place in the NL Central.  It’s been up and down, though; a brutal 10-game losing streak in May almost ruined the momentum of the season, but luckily Craig Counsell was steering the ship in the right direction.  An emergence of Pete Crow-Armstrong as an MVP candidate, along with Nico Hoerner putting up a hot streak since the All-Star break, adds to the excitement Cubs fans have been enduring this season.

Heading into the trade deadline, as they push for a postseason spot in the National League and potentially the NL Central division, the Cubs needed to add to an injury-depleted pitching staff.  

Even though he’s recovering from a broken fibula, Clay Holmes is a dominant starter who, when healthy, boasts a minuscule home run rate and an elite groundball percentage.  Before signing with the Mets, Holmes was a closer for the Yankees, but transitioned to a starter role for the Mets and has been one of the most efficient pitchers in the league.  Before his injury, Holmes was pitching a 2.39 ERA and a 1.10 WHIP across 9 starts.  Along with the Holmes trade, the Cubs also received Tyrone Taylor, who will provide outfield depth and help cover the team’s offensive struggles, as he’s been red hot at the plate.

The Cubs also traded for Kevin Gausman, who brings a strong playoff track record, holding a career 3.83 ERA across 14 postseason games.  Though he has a 5-10 record and a 4.38 ERA at the time of the deal, his strong 3.51 FIP indicated he pitched better than his raw numbers showed. 

Along with Holmes and Gausman, the Cubs added Braxton Garrett for pitching depth and Ryan Zeferjahn to add high-velocity to their bullpen.  Hopefully, the Cubs added the right pitching reinforcements to propel them to the next level and help when needed in the competitive nature of September Baseball.

Pittsburgh Pirates

Coming into the trade deadline, the Pittsburgh Pirates were in a race for the NL Wild Card, as they were only 3.5 games back.  Recently, they’ve lost 8 out of their last 11, with the bullpen being a weak spot.  Injuries have also hampered them left and right, as they’ve lost Ryan O’Hearn, who is out for several weeks, and Mitch Keller has been placed on the 60-day injured list.

To fix the issues, the Pirates traded for stud reliever Luke Weaver, who has dominated this season for the Mets and should’ve been an All-Star.  Weaver has posted a 1.84 ERA and an elite 0.82 WHIP over 42 appearances, to go along with 45 strikeouts and a .162 opponent batting average.  Weaver’s versatility is unmatched, as he can be either the set-up man or the Pirates’ closer

Camilo Doval comes over from the New York Yankees, bringing over high-upside swing-and-miss stuff to the middle or late innings.  Though his season has been up and down, his arm is still elite and intact, featuring a sinker average of 98 mph and a cutter touching triple digits.  Like Weaver, he should help stabilize their late-inning relief corps, and if they can get Doval at his best, then this could be a steal.

They’ve also added Kirby Yates and Lake Bachar to the bullpen, using lower-level organizational depth to provide immediate veteran stability and a multi-inning relief presence.  The influx of high-leverage arms allows existing relievers like Gregory Soto and Mason Montgomery to slide into more optimized, advantageous matchups.

The Pirates went into the deadline and turned a weakness into a strength.  As they fight for a spot in October baseball, they now have the bullpen to help them in late-inning stretches down the line.  

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Brandon Natale
Brandon Natale