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50 Most Notable Yankees Free Agent Signings in 50 Years: Catfish Hunter

The era of free agency in Major League Baseball began in full in 1976, which came after a December 1975 decision from arbitrator Peter Seitz in favor of players Andy Messersmith and Dave McNally, effectively ending the “reserve clause” that had been the law of the land for decades. However, many point to something that […]

Yoshinobu Yamamoto wins Babe Ruth Award as postseason MVP

After a weekend to digest Edwin Díaz’s three-year deal getting finalized and the Dodgers claiming defensive-specialist Michael Siani off waivers, here are a few more stories to start your week. The New York chapter of the Baseball Writers Association of America has bestowed a Babe Ruth Award for the postseason MVP annually since 1949. Yoshinobu […]

Today on Pinstripe Alley – 12/15/25

We rumble along into a fresh offseason week, patiently waiting for the Yankees to make a big move. Amed Rosario was their most recent marginal move, a smart re-signing to give Aaron Boone a much-needed right-handed option that can play across the field. Yesterday, New York was reported to be in on Michael King, which […]

Yankees news: All in on Imai?

Yahoo Sports | Alexander Wilson: It’s been a relatively quiet off-season thus far for the Bronx Bombers. But a report out of Japan hints that may not be the case much longer. The Yankees, if Nikkan Sports is accurate, “will be fully involved in the bidding” for 27-year-old Japanese ace Tatsuya Imai. The price tag […]

Yankees Social Media Spotlight: Wedding Bells

It’s Sunday, and you know what that means — it’s time for our weekly social media roundup! The 2025 Winter Meetings in Orlando, Florida, turned out to be a major dud, at least when it comes to Yankees-related news. Still, despite the lack of baseball news, it was still a big week in the Yankees Universe. […]

Yankees History: Red Ruffing survives a wild day in 1932

You typically need some amount of help to win any baseball game. Even a fairly straightforward 5-1 win that was never really close probably needs a couple bad pitches or some mishit balls to seal the deal. However, everyone appearing in an MLB game is still in the top 0.01 percent of people to play […]

Today on Pinstripe Alley – 12/14/25

The Yankees contined a modest offseason so far by bringing back the versatile Amed Rosario, who played well for them after being acquired from the Nationals at the Trade Deadline. Almost everyone is understandably still twiddling their thumbs and waiting for the Yanks to make their big move, but in the meantime, these edges of […]

Yankees news: Bombers make one addition, as rumors about another emerge

MLB Trade Rumors | Mark Polishuk: While the Yankees would’ve needed some bullpen upgrades regardless, the team has let some of their relief options go this offseason, include Devin Williams going across town to the Mets. In need of some additions back there, the Yankees have reportedly been among a couple teams to check in […]

Yankees re-sign utilityman Amed Rosario

It’s been a quiet offseason for the Yankees. I’ll admit I’ve been one of those positively vibrating to see the Yankees do something. Anything. Saturday afternoon, they made a move that, while it isn’t on the scale of a Kyle Tucker signing, seems like a pretty smart one. New York acquired Amed Rosario from the […]

Breaking down the Yankees’ 2026 ZiPS projections

One of the more interesting things around baseball in 2025 is the disconnect between how the Yankees are viewed by the professional analyst class and the more general population. The former sees them as more or less a perpetual motion machine, churning out quality teams year after year even as they don’t spend what they […]

Yankees Potential Trade Target: Trevor Megill

Whoever said that you can’t repeat the past clearly overlooked the possibility of the Yankees acquiring Trevor Megill during this offseason. Always open to the prospect of bullpen additions, the Yankees could once again ring up Milwaukee to try to pry away their top reliever, hoping, wishing, expecting, contemplating a different outcome than that of […]

Today on Pinstripe Alley – 12/13/25

The offseason slosh continues, as the Winter Meetings fade and we approach the holidays with plenty of big fish still in the sea. It’s not quite the frozen wasteland offseasons of the recent past like when Manny Machado and Bryce Harper were free agents, but its been the first slow burn we’ve seen in a […]

Yankees Mailbag: Gauging Lombard Jr.’s chances for 2026

Good afternoon everyone, it’s time to dive back into the mailbag and answer some of your questions. Remember to send in your questions for our bi-weekly call by e-mail to pinstripealleyblog [at] gmail [dot] com. Chip23 asks: Given Hal’s whining about the payroll and the profitability of the Yankees can we put to rest the notion […]

Yankees 2025 Roster Report Card: Miscellaneous Position Players

Every year during our annual Report Card series here at Pinstripe Alley, we’re generally pretty thorough with who we grade. Obviously, we do full reports on the Aaron Judges and Max Frieds of the roster, but we all will take in depth looks at the likes of J.C Escarra and Ryan Yarbrough. However, there are […]

Yankees Potential Free Agent Target: Luke Weaver

When Luke Weaver joined the Yankees in September of 2023, it was with the lowest of expectations. The former first-rounder and top-50 prospect never fulfilled that pedigree with the Cardinals, who shipped him off to the Diamondbacks as part of a package to acquire Paul Goldschmidt after the 2018 campaign. In his first year with […]

Yankees Potential Free Agent Target: Max Kepler

The 2019 Minnesota Twins were a veritable superteam, boasting a powerful lineup that battered teams into submission. Right in the middle of that success was outfielder Max Kepler, who swatted 36 home runs and 32 doubles while providing quality defense in both center field and right field. His performance, in fact, was so good that […]

Today on Pinstripe Alley – 12/12/25

The Winter Meetings was a bit of a dud this year, but while they were quiet for the Yankees and just about every other team in baseball, they did feature two Mets officially moving on from Queens, with Edwin Díaz leaving for the Dodgers and Pete Alonso signing on with the Orioles. Let’s see if […]

Yankees news: Yanks have gotten calls on Jazz

ESPN: The folks at ESPN put together a roundtable to go over the Winter Meetings, discuss their biggest surprises and letdowns, alongside naming some winners and losers. The Yankees didn’t get mentioned a whole lot thanks to their relative inaction, but they avoided getting much heat for it thanks to teams like the Mets losing […]

Yankees 2025 Roster Report Card: Miscellaneous Pitchers

Every year during our annual Report Card series here at Pinstripe Alley, we’re generally pretty thorough with who we grade. Obviously, we do full reports on the Aaron Judges and Max Frieds of the roster, but we also will take in depth looks at the likes of J.C Escarra and Ryan Yarbrough. However, there are […]

Yankees Potential Trade Target: CJ Abrams

The offseason hot stove ignited during the Winter Meetings with Dylan Cease, Kyle Schwarber, and Pete Alonso all signing megadeals and the Dodgers landing their new closer in Edwin Díaz over the last week. Despite further nine-figure deals expected to be signed in the coming weeks and months, several executives feel that the trade rather […]

Yankees news: New York leaves meetings (mostly) empty-handed

New York Post | Greg Joyce: Brian Cashman spoke again at the winter meetings as the Yankees themselves stayed quiet, and he expressed that things were going very slowly. “We’re just staying engaged, trying… to match up with some things. But it’s been tough so far,” the GM said. “Don’t like the asks coming our […]

Yankees select pitcher Cade Winquest in 2025 Rule 5 Draft

The biggest event of the MLB offseason has come and gone, with the Winter Meetings officially wrapping up on Wednesday in San Diego as the Orioles made perhaps the last splash by signing former Mets masher Pete Alonso to a five-year deal. However, before all the baseball people packed their bags and headed home, there […]

2025 MLB Rule 5 Draft Primer / Preview

2025 MLB Rule 5 Draft Primer / Preview 12/10 UPDATE :  PLAYERS SELECTED BY CUBS IN MAJOR LEAGUE PHASE OF 2025 RULE 5 DRAFT : NONE  CUBS MINOR LEAGUERS SELECTED IN MAJOR LEAGUE PHASE OF 2025 RULE 5 DRAFT :  NONE PLAYERS SELECTED BY CUBS IN AAA PHASE OF 2025 RULE 5 DRAFT :  Adam Stone , RHP (selected for AAA Iowa from New York Yankees Lo-A Tampa roster)  Zane Mill s, RHP (selected for AAA Iowa from St. Louis Cardinals AA Springfield roster)  Devin Ortiz , INF (se...

Yankees 2025 Roster Report Cards: Ryan Yarbrough

As the end of spring training drew to a close, the Yankees were in desperate need for pitching depth, particularly at the back of the bullpen. Suddenly, Ryan Yarbrough, the veteran lefty who spent five years with the Tampa Bay Rays and had signed a minor league deal with the Toronto Blue Jays during the […]

Yankees Potential Free Agent Target: Adolis García

The 2026 Yankees project to have what might be called a fairly high variance group of outfielders. In one locked-in spot, there’s Aaron Judge, a generationally great baseball player who is not going anywhere, or seemingly regressing, any time soon. There’s Trent Grisham, who’s coming off of a surprise career year and an acceptance of […]