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 […]
2 months ago | 3 reads
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 […]
2 months ago | 6 reads
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 […]
2 months ago | 7 reads
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 […]
2 months ago | 2 reads
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 […]
2 months ago | 1 read
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 […]
2 months ago | 2 reads
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 […]
2 months ago | 5 reads
There weren’t many fireworks at this year’s winter meetings, but the last day in Orlando did deliver a pretty surprising move, the Orioles lavishing Pete Alonso with a five-year, $155-million contract. It’s another big addition for an AL East team, and another loss for the Mets, who have seen three fan favorites in Alonso, Edwin […]
2 months ago | 2 reads
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 […]
2 months ago | 3 reads
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 […]
2 months ago | 2 reads
Now, Tuesday was a little more like what we were expecting out of the Winter Meetings. We saw our first big money deal of the event go down, as Kyle Schwarber chose to re-sign with the Phillies on a five-year, $150 million deal over a matching offer from the Orioles and some slightly less-valuable offers […]
2 months ago | 3 reads
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 […]
2 months ago | 6 reads
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 […]
2 months ago | 3 reads
The Winter Meetings are reaching the final lap, and we’ve still yet to see or hear much from the Yankees’ side. After a quiet Monday for the league all-around, we did get some momentum on the market on Tuesday with Kyle Schwarber and Edwin Diaz going to the Phillies and Dodgers, respectively. Perhaps we’ll get […]
2 months ago | 2 reads
USA Today | Bob Nightengale: The proverbial hot stove finally heated up in earnest during day two of the annual winter meetings on Tuesday as two of the offseason’s most coveted free agents agreed to new deals. The Phillies retained DH Kyle Schwarber, fresh off a 56-homer campaign, for five years and $150 million. Meanwhile, […]
2 months ago | 3 reads
For the fourth season now, MLB has staged its draft lottery at the Winter Meetings, this year in Orlando, Florida. With the still-relatively new lottery system, most teams that missed the playoffs the prior season get a chance at winning some top talent, hoping to make their mark in the majors sooner rather than later. […]
2 months ago | 6 reads
Last week, we published our December update to the Top Yankees Prospects list, in which we ranked the 10 most promising minor-leaguers in the farm system. The list was mostly a combination of the team’s most recent first-round draft picks (George Lombard Jr., Spencer Jones, Dax Kilby, Ben Hess) and some breakout starting pitchers (Elmer […]
2 months ago | 1 read
Austin Wells was one of the biggest success stories on the 2024 Yankees, breaking out as a plus-glove and, when on his game, plus-bat catcher who figured to help anchor the lineup in the Bronx for years to come. His second full season in the Show was not a full-blown sophomore slump exactly, but Wells […]
2 months ago | 2 reads
Well, day one at the 2025 Winter Meetings were mostly a bust. There were rumors, but not exactly many of the more juicy variety, and the day was almost completely devoid of actual activity. We did at least hear from Yankees brass, with Brian Cashman telling us that while he doesn’t feel they have as […]
2 months ago | 2 reads
When you think about your archetypical closer, several characteristics spring to mind. They have to possess a high octane fastball they can throw by any hitter. They should be able to rack up strikeouts in bunches. Most importantly, they have to be able to perform in the pressure cooker of the ninth inning, keeping a […]
2 months ago | 4 reads
A quiet first day at the winter meetings came and went, with rumors emanating from Orlando but little actual activity taking place. That’ll likely change at some point this week, but it’s anyone’s guess whether the Yankees will get in on the fun. Regardless of how busy baseball execs are down in Florida, it’ll be […]
2 months ago | 1 read
New York Post | Justin Terranova: The ex must have shown up to Thanksgiving, because the contempt between Sonny Gray and Brian Cashman has only escalated. This time, the Yankee GM has claimed that Gray lied about his desire to pitch in New York back in 2017, and that those supposed lies were the catalyst […]
2 months ago | 2 reads
The New York Yankees entered the 2025 campaign after losing a superstar from their 2024 pennant-winning club to free agency and their ace to season-ending surgery before Opening Day even arrived. Still, their offseason pivot from re-signing Juan Soto landed them some players who helped them return to the postseason with the best record in […]
2 months ago | 5 reads
The Winter Meetings have arrived, and we are at the apex event of the offseason. This is when the most momentum builds towards those star contracts and blockbuster trades, and while this winter has been a quiet one for the Yankees so far there’s hope that things change over the course of this week. The […]
2 months ago | 2 reads
We’re two years plus two days removed from the Juan Soto trade. The Yankees landed one of the very best hitters in the sport, got a top 3 MVP season out of him, went to the World Series. We all knew it was borrowed time — Soto was going to play out his final year […]
2 months ago | 2 reads