Pinstripe Alley
Gary Good, Gleyber Good
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Yankees Potential Trade Target: Joe Ryan
The Twins were the most active sellers at last season’s trade deadline, offloading an incredible ten big league players in a fire sale aimed at both reopening a contention window for 2026 and building a prospect base for their long-term plans. Recent reports indicate that they will not be taking such an axe-handed approach to […]
50 Most Notable Yankees Free Agent Signings in 50 Years: Steve Sax
Sometimes in life, you end up at the right place at the wrong time. Steve Sax was an excellent ballplayer, making five All-Star teams during a distinguished, 14-year career. You could make a strong argument that the best years of his career were spent in pinstripes. And yet, despite his success in baseball’s biggest market, […]
Yankees Potential Trade Target: Nick Lodolo
It’s starting to look like the Yankees won’t be throwing their weight around in the free agency market. It’s possible they’re throwing up smokescreens, but reporting around Christmas that they are not major players for Tatsuya Imai and are in a “holding pattern” with Cody Bellinger suggests the club is either OK with its current […]
Today on Pinstripe Alley – 12/27/25
The baseball world continues to slumber, as the only news to come during this holiday period was Tyler Soderstrom of the Athletics inking a seven-year extension on Christmas (not the worst Christmas gift!). With just a few days left in 2025, we may just have to wait until the new year to see the hot […]
Yankees news: Doval and Rosario updates
Yahoo! Sports | Jared Bloom: The beginning of Camilo Doval’s time with the Yankees did not go as anticipated. After being acquired at the trade deadline, the former San Francisco Giants closer struggled to transition to a mid-inning role. Despite this rough introduction to the pinstripes, however, manager Aaron Boone and the Yankees are “optimistic” […]
Yankees Mailbag: Finding the winter headliner
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. The idiot that said, “Harper is coming” asks: Who do you think will be the biggest name player the Yankees […]
50 Most Notable Yankees Free Agent Signings in 50 Years: Colluding against Guidry and Randolph
Say what you will about the Yankees’ organization, but once you’re considered part of the “True Yankee” family, they’ll generally always roll out the red carpet for you. Say what you will about his decision making and player evaluation capabilities, but George Steinbrenner was always willing to splash the cash to help the Yankees win, […]
Today on Pinstripe Alley – 12/26/25
Happy Boxing Day to all those celebrating, as the holidays start to wrap up and the new year approaches. It remains a slow and steady pace waiting for Yankees news, as they’ve only managed the margins of the roster throughout the days since their elimination from the postseason. A changeup at the very end of […]
Yankees News: Bombers remain confident regarding Bellinger
New York Post | Jon Heyman: ($) Yes, for Christmas, it’s another Cody Bellinger Market update. Heyman reports that the Yankees are feeling “confident” about their chances of re-signing the outfielder, and that they don’t sense that he’ll defect across town like Juan Soto did just one year ago. Heyman also notes that Aaron Judge […]
Today on Pinstripe Alley – 12/25/25
Good morning everyone! We hope you’re having a merry Christmas and a happy holiday. Madison had the overnight news roundup, but the rest of the staff is otherwise understandably off today. If you’re spending time with friends and family today, then great! If you’re trying to escape some for whatever reason or just hanging out, […]
Yankees news: Austin Hays heads the backup plan options
NY Post | Matt Ehalt: The Yankees have had their top priorities set for a while, but they’re still out there waiting to find a new team. In case things don’t end up falling their way and they need to pivot midway through the offseason, a Plan B has to be in place. For the […]
On the brutal pace of the MLB offseason and the Yankees’ inactivity
It doesn’t take a Nobel Prize to be able to deduce that the MLB offseason has the slowest and most brutal pace in all of professional sports. The NBA and NHL have their drafts take place in late June after the conclusion of the postseason, and free agency begins on July 1st. It takes under […]
50 Most Notable Yankees Free Agent Signings in 50 Years: Ed Whitson
As we continue to roll through this “50 Most Notable Yankees Free Agent Signings” series, the majority of the signings we cover are positive, or at least have something positive to add to Yankees history. “Notable,” however, is not an inherently positive descriptor, made clear by our inclusion of Ed Whitson in this series. A […]
Rob Refnsyder and perfectly reasonable prospect outcomes
On Monday night, the Seattle Mariners announced that they had signed outfielder Rob Refsnyder to a one-year, $6.25 million contract, for what will be the 11th season of his big-league career. As a former Yankees farmhand, Refsnyder remains a familiar name to a certain generation of Yankee fans. He struggled during the early part of […]
Today on Pinstripe Alley – 12/24/25
The date is December 24th. Unless you are the world’s biggest Cade Winquest fan (and bless you if you are), the Yankees have yet to bring in any no-doubt major leaguers. That’s a choice! There is time to remedy this but … yeah. Enjoy your Christmas Eves, anyway. Today on the site, Nolan will use […]
Yankees news: Tatsuya Imai hopes fading fast
Sports Illustrated | Delilah Bourque: The Yankees were provided a glimmer of hope in a potential pursuit of starting pitcher Tatsuya Imai. Voices around the industry have singled out the Yankees and Cubs as the likeliest landing spots for the NPB star, and sources recently relayed that Chicago is not one of his preferred landing […]
Yankees Potential Trade Target: Hunter Greene
When you think of the MLB owners who deserve the moniker of Scrooge, Bob Nutting and Bruce Sherman tend to be the first names that come to mind. However, when you combine a miserly attitude toward payroll spending with antagonistic public comments, there are few families who ruin Christmas more for their fans than the […]
50 Most Notable Yankees Free Agent Signings in 50 Years: Phil Niekro
The 1983 New York Yankees finished third in the American League East. Their 91-71 record wasn’t good enough to make the postseason for the second year in a row, but it wasn’t as though they were a team to scoff at, and some improvements could get them back in the hunt. After that season, a […]
Yankees Potential Free Agent Target: Tyler Mahle
Christmas is coming, and while the goose continues to get fat, the Yankees are submitting their final wishes. Among those wishes is likely for some security in the starting rotation to begin the 2026 season. As we’ve mentioned before, the Yankees could have a potentially great group of starters, but with Gerrit Cole and Carlos […]
Festivus Dinner with Pinstripe Alley
Happy Festivus, everybody! I’ve got a lot of problems with you people. Now, you’re gonna hear about it! No, I don’t mean you, dear readers. I’m obviously referring to the Yankees! Every fan who follows their team with any degree of regularity will start to have that team get on their nerves in a variety […]
Today on Pinstripe Alley – 12/23/25
Just two days from Christmas, today’s the last day MLB execs can make moves without infringing on their own (and our) holidays. It’s likely to be a slow week in what’s felt like a slow offseason, though I think this makes it a good time to reflect on what’s actually happened. Even if things seem […]
Yankees news: Can the bullpen be trusted in 2026?
The Athletic | Chris Kirschner: Over the past two seasons and playoff runs, the reliability of the Yankees’ bullpen has been one of the major questions plaguing the team. The organization has been decent at being able to squeeze good innings out of the likes of Ian Hamilton and Tim Hill at points, but it’s […]
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 […]
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