Pinstripe Alley
Gary Good, Gleyber Good
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Ask Pinstripe Alley: Yankees mailbag questions request
The offseason hasn’t quite moved at a snail’s pace, but for the Yankees it might as well have. Leaks have either been all but nonexistent from the front office this year, or there simply hasn’t been anything for them to leak out to the public. The outfield conundrum remains undecided, with Cody Bellinger and Kyle […]
50 Most Notable Yankees Free Agent Signings in 50 Years: Don Baylor
In the late 1970s, George Steinbrenner’s ways of spending big and throwing things at the wall to see what sticks worked out to the tune of two World Series championships and another AL pennant. That probably emboldened him to do even more of that in the 1980s, and that… did not work out as well. […]
Tyler Skaggs, and why can’t we be better
Here’s the thing about human beings: we’re pretty good at asking for what we need, and finding alternatives when we can’t get it. In the early-to-mid-90s, thousands of men begged governments for access to AZT drugs, the only thing that could save their lives as HIV/AIDS wiped out a generation. Many of these men turned […]
Today on Pinstripe Alley – 12/22/25
The division saw another sizeable move occur, as Boston jumped back into the mix with another trade with St. Louis — this time going for Willson Contreras to play first base for them. They gave up a few pieces, including pitcher Hunter Dobbins as the headliner, so he won’t have to worry about antagonizing Yankees […]
Yankees news: NPB star Munetaka Murakami heads to the South Side
MLB.com | Mark Feinsand: By now you’ve likely heard that NPB superstar Munetaka Murakami signed a two-year, $34 million deal with the White Sox yesterday. It was somewhat of a surprise both in terms of the deal size and the team, although no real rumors had swirled around Murakami in his entire posting process. I […]
Yankees Social Media Spotlight: Holiday Service
It’s Sunday, and you know what that means — it’s time for our weekly social media roundup! It’s been a big week for New York sports, as the Knicks brought home the NBA Cup and to ensure that the Big Apple wouldn’t end 2025 without a trophy of some kind. But what have our Yankees […]
Fun with video games: Crowning the best-ever Yankees team
If you have any interest in the history of baseball and the Yankees, you’ve probably wondered what the best Yankees team of all-time might be. However, unless someone invents a real time machine anytime soon, there’s no real way to figure that out. Even then, just dropping the 1927 Yankees into 1998 for a series […]
Today on Pinstripe Alley – 12/21/25
I am typing this just before midnight and cackling a bit. This is already in our overnight news, but apparently the Yankees just re-signed Paul Blackburn. Jon Heyman reported this. The beat writer life ain’t glamorous when your job compels you to break such minor news quite late on a Saturday night. It’s a major-league […]
Yankees news: Paul Blackburn re-signs with New York
MLB Trade Rumors | Charlie Wright: How about a super-late Saturday night news dump? Just about half an hour before PSA’s news roundup was set to go live, Jon Heyman reported that the Yankees were bringing back pitcher Paul Blackburn, who they picked up off the scrap heap in August 2025 in a manner quite […]
A naughty and nice list for the 2025 Yankees
We’re still a few days away from Santa Claus’ overnight flight to deliver gifts around the world, so that gives us more time to think about who should be receiving them. Traditionally, Santa has a “nice list” on which the good kids who receive a visit from him are, and a “naughty list” where bad […]
50 Most Notable Yankees Free Agent Signings in 50 Years: Dave Collins
They say first impressions last the longest, but what about first impressions being the only impressions? And if you fail to hit the ground running, it’s on to the next one in line? The Yankees experienced this with Dave Collins back in 1982. A strange strategic choice of their own volition, Collins had one disappointing […]
Yankees Potential Free Agent Target: Justin Verlander
As the offseason ticks along, more and more free agent dominos begin to fall. With the new year around the corner, the Yankees likely still have some moving to do, particularly when it comes to filling the early season voids in the rotation. Gerrit Cole and Carlos Rodón are both expected to begin the 2026 […]
Today on Pinstripe Alley – 12/20/25
The division rival Rays were active on the trade market yesterday in another edition of sending their more experienced (read: expensive) players away, with longtime second baseman Brandon Lowe going to the Pirates as part of a three-team trade and pitcher Shane Baz going to the Orioles for four prospects and a 2026 Competitive Balance […]
Yankees news: Aaron Boone talks Chisholm, Imai, and Rosario
The Sporting News | Justin Backer: Recent weeks have shown that, while the Yankees are not explicitly shopping second baseman Jazz Chisholm Jr., they have been willing to listen when teams have inquired about his availability. Even so, all indications are that the team expects to start season with Chisholm penciled in at second base. […]
50 Most Notable Yankees Free Agent Signings in 50 Years: Dave Winfield
When a future Hall of Famer signs a 10-year deal to join a new team, that contract is usually remembered first and foremost for how that player performs on the field. Over that length of time, an elite talent will generally put up the types of numbers and generate the types of iconic moments that […]
Yankees Potential Free Agent Target: Zack Littell
The Yankees’ starting rotation projects as one of the weak links in the opening months as Gerrit Cole, Carlos Rodón, and Clarke Schmidt are all set to miss the start of the season while recovering from their respective surgeries. However, outside of Tatsuya Imai, the front office is expected to sit on the sidelines when […]
Yankees History: The unexpected hitting heroics of pitcher Bob Grim
There are many things different about the way baseball is played from 1957 to today. There’s probably not anything that makes that more apparent than pitcher usage in general. These days, pitchers don’t throw nearly as many innings as they used to, as teams rely heavier on bullpens than they used to. Complete games are […]
Today on Pinstripe Alley – 12/19/25
The offseason saw some motion on Thursday, with Michael King inking a new deal to go back to the Padres. King wasn’t quite at the top of the starting pitcher market after an injury-marked 2025, but his transition into the rotation the last two years has been a resounding success and he got paid for […]
Yankees news: Why the Yankees broke a 14-year streak
MLB.com | Bryan Hoch: The Yankees hadn’t selected anyone in the Rule 5 Draft since 2011, until they took Cade Winquest this year. What possessed them to turn the tables and actually take a player in the Rule 5 for once? “He’s got big velocity,” assistant GM Michael Fishman said. “He has characteristics that our […]
Yankees Potential Trade Target: Freddy Peralta
Two seasons ago, fresh off a 92-win campaign and an NL Central division title, the Milwaukee Brewers traded their best pitcher. Former Cy Young winner Corbin Burnes, entering his final year before free agency, was dealt to the Orioles for a fairly underwhelming return. Nonetheless, the Brewers remained the class of their division, in fact […]
50 Most Notable Yankees Free Agent Signings in 50 Years: Tommy John
Aside from perhaps only the Jackie Robinsons and Babe Ruths of the baseball canon, few other names are tossed around as frequently as that of Tommy John. Although his ubiquitous acknowledgement comes more from a revolutionary medical procedure than a reputation as a player, Tommy John stuck in the big leagues for more than a […]
Yankees Potential Trade Target: Sandy Alcantara
There is perhaps no pitcher who has seen his name surface in trade rumors more over the last five years than Sandy Alcantara. Practically from the day he inked his five-year, $56 million extension, speculation swirled as to when the miserly Marlins ownership group would look to get out from under the rest of the […]
Today on Pinstripe Alley – 12/18/25
The Yankees continue to bide their time, and we’ll have to continue to hope they’re just waiting to pounce. Yesterday, we saw the Yankees-to-Mets pipeline strengthen even further, Luke Weaver defecting to Queens for two years and $22 million. The Mets have now successfully recreated the Yankees’ late-inning combo from the first half of the […]
Yankees news: Cubs, Yanks finalists for Tatsuya Imai
The Sporting News | Matt Sullivan: The Yankees have yet to make a major splash this winter, even as more than one key member of the bullpen has left the team — more on that in a moment. We get a bit of good news on that front, with reports that New York is one […]
Former Yankees reliever Luke Weaver signs with Mets
Get a new bit, Mets. Weeks after signing Devin Williams in wake of the the Airbender’s tricky season in the Bronx and one offseason removed from signing Juan Soto and Clay Holmes, that other New York team has come to terms with yet another erstwhile Yankee. This time, it’s reliever Luke Weaver going to Queens […]
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