With the MLB trade deadline less than a week away—closing at 6 PM ET on July 31, 2025—New York Yankees general manager Brian Cashman is operating under immense pressure. The team sits well behind the AL East–leading Blue Jays, and a recent injury to Aaron Judge only adds urgency to a season that’s teetering.
1. Where Things Stand: Blue Jays in Command, Yankees Stalling
Once boasting a commanding lead in the division, the Yankees now trail Toronto by several games with only about 60 regular-season contests left. A 14‑23 run since mid‑June reflects New York’s traditional post–All‑Star break swoon, worsening the trade deadline stakes.New York PostKeefe To The City
Cashman has acknowledged that starting pitching, bullpen relief, and a third baseman are top priorities—a promise he backed up with recent dealings. Still, in the wake of recent underperformance and heightened expectations, executives and fans alike are watching closely.SI
2. Judge Injury Cracks the Foundation
Superstar Aaron Judge is sidelined with a right forearm flexor strain, likely missing at least ten days. An MRI confirmed no elbow UCL damage—avoiding Tommy John surgery—but Judge’s absence further exposes the Yankees’ thin depth and intensifies trade pressure.Wikipedia+15Pinstripe Alley+15New York Post+15
This unfortunate news came just after two deadline moves had already been made, raising questions about whether more targeted acquisitions will follow.Keefe To The City+15EssentiallySports+15Pinstripe Alley+15
3. Deadline Moves So Far: Infield Bolsters Arrive
In recent days, Cashman completed the following transactions:
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Ryan McMahon acquired from the Rockies to bring power and stability to third base.
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Amed Rosario picked up from the Nationals to bolster infield versatility and bench depth.
These addresses were aimed directly at shoring up New York’s infield woes—but even with those additions, pitching remains the primary need.Yanks Go Yard+1New York Post+1Pinstripe Alley+7SI+7Pinstripe Alley+7
Despite serving his purpose, these moves aren’t blockbuster-shaking—and many believe stronger moves may still be on the table.Yanks Go YardPinstripe AlleySI
4. What’s Still Needed: Rotation, Relief, and Potential Bat Help
🧢 Starting Pitching
The Yankees remain in search of an ace-level starter, preferably someone like Zac Gallen or Merrill Kelly, to complement their rotation amid recent injuries and inconsistent performances.Pinstripe Alley
🧢 Bullpen Reinforcements
New York’s relievers have struggled mightily. With a July ERA of 7.10 and the worst AL bullpen WAR, the Yankees are eyeing relievers such as Jake Bird from the Rockies or David Bednar from Pittsburgh. Bird’s strong underlying metrics (FIP, xFIP) despite recent runs allowed make him a compelling—if risky—target.Pinstripe Alley
🧢 A Right-Handed Bat?
Though infield depth has improved, the team may still pursue a versatile right-handed hitter—possibly someone like Isiah Kiner-Falefa or Willi Castro—to offset Judge’s absence and add lineup flexibility. Recent reporting suggests such a move is still on the table.New York Post
5. The Big Decision: Sell, Hold or Buy?
With the Yankees firmly in win-now mode—and Judge in his prime—Cashman is under pressure to make impactful moves. One camp believes he must be aggressive: spend prospect capital to address rotating and bullpen failures. Others argue that top prospects like Cam Schlittler should be off-limits given their long-term upside, and safer trades should be made instead.Pinstripe Alley
Yet New York has precedent for pulling surprising deadline turnaround efforts; Cashman is known for bold phone calls—but this year, even that will need to yield results.New York PostESPN.com
6. How It Could Shape the Final Weeks
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A successful haul of a starter, reliever(s), and bench bat could rejuvenate the lineup and rotation, helping close the gap in the AL East.
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Failure to land impactful help might commit the Yankees to a wild-card route.
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Or, if no major moves occur, the team risks a stagnant stretch in outfield depth—or exaggerating Judge’s absence longer than necessary.
Veteran postseason experience and the postseason-driven “If not now, when?” perspective weigh heavily on Cashman’s fan-facing credibility.
✅ Final Thoughts
As of July 28, 2025, the trade deadline looms as the defining moment of the Yankees’ season. With Aaron Judge sidelined, defensive flaws, inconsistent pitching, and a standings deficit behind the Blue Jays, Brian Cashman must now deliver. While recent deals brought some infield depth, many believe that acquiring frontline pitching and bullpen reinforcements is non-negotiable. Whether he dares to trade top prospects or stays the course could seal the Yankees’ fate for 2025.
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