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50 Most Notable Yankees Free Agent Signings in 50 Years: Brian McCann

The 2013 New York Yankees finished the season 85-77, good for third place in the American League East and on the outside looking in at the playoffs when the regular season concluded. Their “leaderboard” is a veritable who’s who of guys who certainly played in the major leagues. 36-year-old’s Travis Hafner and Lyle Overbay, 34-year-old […]

From Pinstripe Alley | about 2 hours ago | 0 reads

Yankees 2026 Season Preview: José Caballero

Any description of José Caballero’s playing style will probably include something along the lines of “pest” or “hate him on other teams, love him when he plays for your team.” Well, as of last year at the trade deadline, he’s on our team. Looking to improve on the depth of the roster, the Yankees picked […]

From Pinstripe Alley | about 4 hours ago | 1 read

Introducing the Yankees Birthday Series

During my tenure at Pinstripe Alley—hell, during my entire time as a baseball fan—I’ve never been shy about delving into the team’s history and exploring the lives of its long roll call of players, both incredible and regrettable. We provide plenty of other coverage on the current-day activities of the teams, so I like having […]

From Pinstripe Alley | about 6 hours ago | 4 reads

Yankees Birthday of the Day: Roger Peckinpaugh

Almost a century before Derek Jeter manned shortstop and held the captaincy for the New York Yankees, another athletic young player did the same. Roger Peckinpaugh, who came to the Yankees at the age of 20, never experienced the level of team success that Jeter did, nor could he boast a similar offensive profile. But […]

From Pinstripe Alley | about 6 hours ago | 2 reads

The milestones Yankees will be chasing in 2026

Giancarlo Stanton sits 47 home runs away from 500 for his career, that nice round number that counts for quite a bit in Hall of Fame discussion. It does feel like that chase will come right down to the wire, with Stanton’s contract running through the 2027 season but with some kind of labor stoppage […]

From Pinstripe Alley | about 8 hours ago | 1 read

Which version of Gerrit Cole will the Yankees get this season?

So, the Yankees are running it back 2026. As frustrating as that will feel to many (cue the “getting Gerrit Cole back is like trading for an ace!” proclamations from Yankee brass), there is reason to be optimistic about the strategy. The team that they’re running went an MLB-best 32-12 down the stretch, and at […]

From Pinstripe Alley | about 10 hours ago | 0 reads

Yankees news: Beating projections seems viable for several Yanks

MLB.com | Brian Murphy: The Yankees have a very similar team to the one that they ran in 2025, meaning that they have to be confident that they’ll see improvement in at least a few key areas to get them over the hump. They’re got a few candidates to step up, including ones that began […]

From Pinstripe Alley | about 16 hours ago | 1 read

The 50 Most Notable Yankees Free Agent Signings in 50 Years

Major League Baseball was forever changed 50 years ago this month. That was when arbitrator Peter Seitz ruled in favor of pitchers Andy Messersmith and Dave McNally against the league. The two had played 1975 after refusing to sign contracts for their respective teams and the opportunity had finally arrived in full for the MLB […]

From Pinstripe Alley | about 17 hours ago | 4 reads

Red Sox sign free agent infielder Isiah Kiner-Falefa

Who is he and where did he come from? He’s Isiah Kiner-Falefa. The former Ranger also spent time with the Yankees before signing a 2-year, $15 million deal with the Blue Jays in 2024, who then traded him to the Pirates at that year’s trade deadline, only to take him back a year later after […]

From Over the Monster | about 18 hours ago | 1 read

Presenting the 2026 Yankees Roster Season Preview

The long night of the offseason is approaching its conclusion! Pitchers and catchers report to the Tampa spring training complex in nine days as of the time that this post goes up, and we’ll have exhibition games beginning on February 20th against the Orioles. Opening Day in San Francisco is just over a month after […]

From Pinstripe Alley | 1 day ago | 2 reads

Yankees 2026 Season Preview: Paul Blackburn

When it comes to pitching, top-end talent is crucial. So, too, is depth. The ability to find pitchers to “eat innings” — entering in lower-leverage situations or filling in the back end of rotations and pitching competitively — can help reduce wear on the rest of the staff. Sometimes, those supposed innings eaters end up […]

From Pinstripe Alley | 1 day ago | 1 read

The Yankees’ bullpen is tough to sell as ready for 2026

While we’ve only just begun the month of February, Major League Baseball’s 2026 spring training is fast approaching. Teams are gearing up for what is set to be another interesting season with plenty of ups and downs for every player and club. The New York Yankees are no different. GM Brian Cashman and company feel […]

From Pinstripe Alley | 1 day ago | 2 reads

The Yankees’ bullpen is far from perfect, but its upside is undeniable

The Yankees’ roster might not be a finished product. They are openly looking for a right-handed bat from the bench, and one or two bullpen additions surely wouldn’t hurt. They have, apparently, decided to open the season with their current group of starters, knowing that an injury or two in spring training could mean trouble […]

From Pinstripe Alley | 1 day ago | 2 reads

Yankees Birthday of the Day: Lefty Davis

The history of the Yankees dates back to the start of the 20th century and a humble team known then as the New York Highlanders. Their first ever game was played on April 22, 1903, against the Washington Senators, a 3-1 loss at American League Park, one of the more well-known Griffith Stadium’s predecessors in […]

From Pinstripe Alley | 1 day ago | 1 read

Which past Yankees season still bothers you the most?

Welcome to Wednesday. The Yankees’ pitchers and catchers will officially report to spring training a week from today! Hurrah. There’s not much else going on though, so we’ll get into today’s discussion prompt. The Yankees have won 27 championships of course, but there have still been plenty of seasons that ended with frustrating results. Here’s […]

From Pinstripe Alley | 1 day ago | 1 read

Yankees news: Searching for one more hitter

New York Post | Joel Sherman ($): The Yankees seem like they’re hunting for one more addition, preferably a right-handed hitter who can play multiple positions. We don’t know much about the status of utilityman Oswaldo Cabrera as he returns from his grisly ankle injury, and the team may prefer a player with a little […]

From Pinstripe Alley | 1 day ago | 1 read

Michael Siani finds his way back to Dodgers

The Michael Siani offseason rollercoaster looped around to make a second stop in Los Angeles, as the center fielder was claimed by the Dodgers off waivers from the New York Yankees on Tuesday. This comes 11 days after the Yankees claimed him off waivers from the Dodgers. It’s been a busy offseason for the defense-first […]

From True Blue LA | 2 days ago | 1 read

50 Most Notable Yankees Free Agent Signings in 50 Years: Rafael Soriano

It’s January 2011 and the Yankees have narrowly missed out on the opportunity to defend their World Series crown, having been bounced out of the ALCS by the Rangers in six games. One of the players most responsible for their demise — and a personal white whale for general manager Brian Cashman — has just […]

From Pinstripe Alley | 2 days ago | 0 reads

Yankees 2026 Season Preview: Cody Bellinger

Following two seasons with the Chicago Cubs and eight in the National League, Bellinger found himself in a very different (but also familiar) environment after he was dealt to the New York Yankees in December of 2024. Bellinger’s dad, Clay, was a Yankee from 1999-2001, winning two World Series championships with the team before playing […]

From Pinstripe Alley | 2 days ago | 0 reads

Yankees Birthday of the Day: Chicken Hawks

Some baseball players are memorable for having long and successful careers. Some are memorable for coming up with a huge play or hit in a big moment. Some are memorable for the wrong reasons, like making a mistake in a big moment or for some other controversial reason. Then, there are some who are memorable […]

From Pinstripe Alley | 2 days ago | 1 read

State of the Yankees’ System: Outfield

The Yankees’ outfield is loaded with star power on both sides of the ball, as any group led by Aaron Judge should be. The generational slugger won his third AL MVP award in 2025 after yet another season that had to be seen to be believed: .331/.457/.688 (a career-high in batting average), 53 home runs, […]

From Pinstripe Alley | 2 days ago | 1 read

Who will have the Yankees’ best season in the rotation this year?

We’re three days into February, and by now you’re likely familiar with our new format to kickstart our days. The Yankee rotation was one of the focal points of the offseason right after the No. 1 priority of dealing with the outfield, and while they ultimately didn’t do much outside of adding some depth arms […]

From Pinstripe Alley | 2 days ago | 1 read

Yankees news: Yanks interested in former Gold Glover Ty France

CBS Sports | R.J. Anderson: The Yankees are one of several teams interested in Ty France, per MassLive.com’s Chris Cotillo. The Red Sox, Mets, Padres, and Diamondbacks are among the first baseman’s other suitors. France slashed .257/.320/.360 last year in 138 games with the Twins and Blue Jays. This report comes on the heels of […]

From Pinstripe Alley | 3 days ago | 2 reads

Ask Pinstripe Alley: Yankees mailbag questions request

We’re finally in the home stretch of the offseason. Spring training is just a couple of weeks away, and before we know it the 2026 Yankees will be taking the field and playing ball with the goal of avenging their disappointing finish last year. This is true moreso than most teams that got bounced because […]

From Pinstripe Alley | 3 days ago | 2 reads