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50 Most Notable Yankees Free Agent Signings in 50 Years: Reggie Jackson

By the mid-1970s the Yankees were starting to get over that hangover of some 30 years of baseball dominance, with the team finding a clutch of new young talent to replace the legends like Mickey Mantle or Whitey Ford who had eventually left the sport. Thurman Munson was the captain by 1976, Graig Nettles was […]

From Pinstripe Alley | about 1 month ago | 4 reads

2025 Dodgers season review: Blake Treinen

Twelve months ago, Blake Treinen was a folk hero, as the lanky and taciturn, salt-of-the-earth reliever who bent but never broke getting critical outs as the Dodgers vanquished the New York Yankees with aplomb, earning himself both a bobblehead night on August 17, 2025, and a new two-year contract. With new addition-Tanner Scott to man […]

From True Blue LA | about 1 month ago | 4 reads

Yankees International Winter Ball Update

With the offseason in full swing, the only prospects currently playing baseball are doing so outside the mainland U.S. where the weather is warm. The Yankees currently have five players participating in Winter Ball, including a few who spent time with the big-league club in 2025 and at least one who should compete for a […]

From Pinstripe Alley | about 1 month ago | 1 read

Chicago Cubs news and notes — Ballesteros, Imai, King

Luke Weaver is the latest name floating around in the blogosphere. Michael King is said to have reduced his potential landing spots to three AL East cities. The sources are credible but nothing is definite yet. *means autoplay on, (directions to remove for Firefox and Chrome). {$} means paywall. {$} means limited views. Italics are often used on this page […]

From Bleed Cubbie Blue | about 1 month ago | 4 reads

Today on Pinstripe Alley – 12/16/25

The offseason hibernation continues for New York, with little new to say about them. They are reportedly listening in on offers for second baseman Jazz Chisholm Jr., one of their best bats in the lineup, as a potential avenue to upgrading the pitching staff, but listening is a long ways away from agreeing to anything. […]

From Pinstripe Alley | about 1 month ago | 2 reads

Yankees news: Bombers open to trading Jazz

MLB.com | Bryan Hoch: The Yankees are the only team in the AL East who hasn’t completed a big deal this offseason, and now it’s suggested that their first major piece of offseason business could be a departure rather than an arrival. Jazz Chisholm Jr. has attracted interest from several rival teams, and while Brian […]

From Pinstripe Alley | about 1 month ago | 3 reads

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 […]

From Pinstripe Alley | about 1 month ago | 3 reads

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 […]

From True Blue LA | about 1 month ago | 4 reads

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 […]

From Pinstripe Alley | about 1 month ago | 4 reads

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 […]

From Pinstripe Alley | about 1 month ago | 2 reads

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. […]

From Pinstripe Alley | about 1 month ago | 5 reads

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 […]

From Pinstripe Alley | about 1 month ago | 3 reads

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 […]

From Pinstripe Alley | about 1 month ago | 4 reads

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 […]

From Pinstripe Alley | about 1 month ago | 4 reads

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 […]

From Pinstripe Alley | about 1 month ago | 3 reads

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 […]

From Pinstripe Alley | about 1 month ago | 3 reads

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 […]

From Pinstripe Alley | about 1 month ago | 2 reads

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 […]

From Pinstripe Alley | about 1 month ago | 2 reads

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 […]

From Pinstripe Alley | about 1 month ago | 2 reads

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 […]

From Pinstripe Alley | about 1 month ago | 2 reads

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 […]

From Pinstripe Alley | about 1 month ago | 4 reads

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 […]

From Pinstripe Alley | about 1 month ago | 6 reads

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 […]

From Pinstripe Alley | about 1 month ago | 2 reads

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 […]

From Pinstripe Alley | about 1 month ago | 1 read

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 […]

From Pinstripe Alley | about 1 month ago | 1 read