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Pinstripe Alley

Gary Good, Gleyber Good

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Yankees Birthday of the Day: Ryan Thompson

On November 4, 2026 the Pinstripe Alley celebrates former Yankee outfielder Ryan Thompson’s birthday. Born in 1967 in Chestertown, MD, Thompson was a 13th‑round pick by Toronto in 1987 and debuted with the Mets in 1992. After stints with Cleveland, Japan’s Fukuoka Daiei Hawks, and the Astros, he joined the Yankees for the 2000 season, posting a .260/.339/.500 line in 33 games and hitting a three‑run homer on July 14 against the Marlins. Though he didn’t play in the postseason, he earned a World Series ring as New York beat the Mets. Thompson’s nine‑year MLB career also included time with the Marlins and Brewers before retiring after the 2004 minor‑league season.

Yankees 2026 Roster Report Cards: Angel Chivilli

The Yankees' 2026 roster report card for reliever Angel Chivilli highlights a turbulent season marred by injuries but underscored by flashes of potential. Acquired from Colorado for T.J. Rumfield, Chivilli posted a 3.78 ERA (113 ERA+) over 15 games for New York, striking out 21.9% of batters but also walking 9.6%. After strong Triple‑A outings, he earned a July call‑up and delivered a 12‑inning scoreless stretch before a disastrous August 8‑run collapse against the Cardinals ended his MLB stint. He finished the year with a dominant 0.57 ERA in Triple‑A and a 32.6% whiff rate, leaving his grade incomplete and his 2027 pre‑arbitration outlook uncertain.

Today on Pinstripe Alley – 11/4/26

Pinstripe Alley’s November 4 roundup looks at the early offseason buzz as a potential MLB lockout looms. ESPN’s Kiley McDaniel hints the Yankees are eyeing Tigers pitcher Tarik Skubal, sparking speculation about a pre‑CBA deadline deal before the collective bargaining agreement expires on Dec. 1. The post also recaps John’s grade on Angel Chivilli’s injury‑plagued 2026 season, Matt’s Yankee Birthday spotlight on a forgotten 2000 World Series player, and Estevão’s analysis of AL playoff flaws. Readers are invited to weigh in on whether a transaction frenzy will hit the Yankees and what Skubal’s contract might look like before a possible lockout.

Yankees news: Skubal linked to Yanks

The Yankees are reportedly weighing a blockbuster move for two‑time Cy Young winner Tarik Skubal, the top free‑agent pitcher on the market, which could force them to trade away other starters. While the Dodgers and Mets lead the chase, clubs like the Angels, White Sox and Padres linger as dark‑horse options. Meanwhile, Brewers manager Pat Murphy apologised after a hot‑mic jab at New York sparked controversy, and the Yankees have moved on from Jazz Chisholm Jr., who did not receive a qualifying offer after a mixed season. The article rounds up the key free‑agency targets and lingering drama ahead of the offseason.

Yankees icons Lou Piniella, Bill White featured on crowded Hall of Fame committee ballot

The National Baseball Hall of Fame’s non‑player Era Committee is set to vote on eight nominees, three of which have strong New York Yankees ties. The ballot includes legendary manager Dusty Baker, who boasts 1,981 hits, 242 homers, a 2022 World Series title and three Manager of the Year awards, and other notable Yankees figures such as former manager Lou Piniella and executive Bill White. To be inducted, a candidate must earn at least 12 of the 16 votes from the 16‑member committee, which can select up to three inductees. The article breaks down each nominee’s credentials and odds, highlighting how the committee’s broader career‑wide evaluation could benefit former Yankees.

Presenting the 2026 Yankees Roster Report Cards

Pinstripe Alley launches its 2026 Yankees Roster Report Card series, grading every key player after the ALDS loss to the Rays. Starting mid‑October and running to early December (skipping Thanksgiving and weekends), the staff‑averaged grades are posted with release dates—from David Bednar (A) on Oct 23 to Anthony Volpe (Dec 4) and final miscellaneous categories on Dec 10‑11. Manager Aaron Boone and GM Brian Cashman are excluded, but links to their evaluations are provided.

Yankees Birthday of the Day: Paul Quantrill

On November 3, 2026 Pinstripe Alley honors former Yankee reliever Paul Quantrill, born Nov. 3, 1968 in Ontario. After debuting with Boston in 1992, Quantrill forged a 14‑year MLB career, most notably as a workhorse out of the Toronto bullpen (league‑leading appearances in 2001) and later with the Yankees, where he logged 86 games in 2004 and posted a 3.26 ERA before fatigue surged, culminating in a costly walk‑off home run to David Ortiz in the ALCS. He finished his stint with brief stops in San Diego and Miami, and also represented Canada internationally. The piece traces his journey from college standout to the “appearance king” and reflects on the toll of heavy usage on relievers.

Yankees 2026 Roster Report Cards: José Caballero

José Caballero earns a C+ on the Yankees’ 2026 roster report card. With Anthony Volve sidelined early, Caballero started Opening Day at shortstop, even becoming the first player to challenge a pitch via the automated ball‑strike system. He posted a .231/.290/.365 line with 14 homers, 51 RBI, 83 wRC+, 1.3 fWAR over 136 games, but a May finger injury knocked him out of the shortstop role as Volve returned. Caballero’s late‑season utility work included quirky pitch‑clock disputes and a drop to a .623 OPS after his return. He’s arbitration‑eligible for 2027 and likely to remain a versatile bench piece for New York.

Should the Yankees have given Jazz Chisholm Jr. the qualifying offer?

The Pinstripe Alley column debates why the Yankees withheld a $23.15 million qualifying offer from Jazz Chisholm Jr. after his disappointing 2026 season, where his slugging fell below .400 despite 41 steals. The piece contrasts his situation with Trent Grisham’s similar QO gamble and notes the lack of reliable second‑base alternatives like Luis Arraez or Brandon Lowe. While Chisholm’s career .756 OPS and past power‑speed flashes suggest a rebound potential, his poor performance against lefties and budget concerns under Hal Steinbrenner make a one‑year deal risky. The article concludes the Yankees likely prefer a safer, bigger investment over a costly, uncertain short‑term contract for Chisholm.

Why have the Yankees kept all their coaches?

The Yankees are likely to retain their entire coaching staff for 2027, despite a disappointing 2026 season that saw the team’s offense drop to 739 runs and a wRC+ decline of 17 points. Pitching coach Matt Blake, praised for developing Cam Schlittler and cost‑effective bullpen arms, is expected to sign a new deal, while hitting coach James Rowson and third‑base coach Luis Rojas appear set to return. Owner Hal Steinbrenner and GM Brian Cashman blamed the players for the slump, emphasizing a salary‑cap focus amid looming labor talks. With no major roster overhaul anticipated, the same coaches will guide a largely unchanged squad next year.

Today on Pinstripe Alley – 11/3/26

The Yankees issue a qualifying offer to reliever David Bednar but decline to extend one to Jazz Chisholm Jr., signaling the likely end of his New York stint as he heads into free agency without draft‑pick compensation. The blog also previews commentary on Aaron Boone's coaching staff, grades José Caballero’s 2026 season, a birthday tribute to former Yankee Paul Quantrill, and a Hall of Fame Era Committee preview featuring managerial and executive nominees.

Yankees news: No qualifying offer for Jazz Chisholm Jr.

The Yankees skip a qualifying offer for Jazz Chisholm Jr., leaving the 28‑year‑old shortstop out of the $23 million QO market while extending that deal to closer David Bednar, who must decide by Nov. 17. Analyst Ben Clemens warns a sluggish offseason amid looming CBA talks, noting limited high‑ceiling free agents beyond top prospect Tarik Skubal. Meanwhile, New York Post highlights the Bednar offer, NJ.com flags NPB star Teruaki Sato as a potential target, and MLB Trade Rumors reports infielder Marco Luciano’s addition to the 40‑man roster.

Cam Schlittler named finalist for AL Cy Young among BBWAA award announcements

Cam Schlittler, the 25‑year‑old Yankees ace who posted a league‑best 1.95 ERA and 6.2 FANGRAPH WAR, is named the sole AL finalist for the Cy Young Award alongside Dylan Cease and Parker Messick. MLB Network will announce the winner on Nov. 11, with the NL nominees including Jacob Misiorowski, Chris Sale and Cristopher Sánchez. The post also outlines other BBWAA finalists – MVP hopefuls Yordan Alvarez, Junior Caminero and Bobby Witt Jr.; Rookie of the Year candidates such as Mets outfielder Carson Benge; and new Reliever of the Year nominees – highlighting the Yankees’ limited representation beyond Schlittler.

Yankees extend qualifying offer to David Bednar

The Yankees have tendered a qualifying offer (QO) solely to reliever David Bednar, giving him until Nov. 17 to accept the $23.15 million one‑year deal that would make him the highest‑paid reliever in MLB. While the team expected to extend a QO to Jazz Chisholm Jr., his uneven 2026 season left him off the list. Bednar, a key bullpen stabilizer in his early‑30s, is likely to test free agency, though rejecting could earn the Yankees draft‑pick compensation. He joins seven other players—including Randy Arozarena and Seiya Suzuki—who received QOs this year.

Ask Pinstripe Alley: Yankees mailbag questions request

The Pinstripe Alley mailbag invites fans to weigh in on the Yankees' 2026 award season. Cody Bellinger clinches the Gold Glove as the AL's top defensive left fielder, while Austin Wells and Jose Caballero earn finalist nods at catcher and utility. The piece also highlights Cam Schlitter’s Cy Young candidacy and his potential MVP placement despite a lackluster team finish. Readers are asked to submit their own standout picks and “Razzies” for the squad by Nov. 5, with answers posted Friday afternoon.

Yankees Birthday of the Day: Jonathan Loáisiga

Celebrating Jonathan Loáisiga’s birthday, Pinstripe Alley recounts his unlikely rise from a cut free agent in 2016 to a key Yankees reliever. After Tommy John surgery and a series of injuries, the Nicaraguan right‑hander debuted in 2018, striking out six over five scoreless innings against the Rays. Transitioned to a full‑time bullpen role in 2021, Loáisiga posted a 2.4 fWAR and a 2.18 xERA, ranking just behind Liam Hendriks and Josh Hader. Subsequent seasons were marred by shoulder issues, bone spurs, and another UCL injury, leading the club to decline his 2026 option. The piece highlights his career highs, setbacks, and lasting impact on the Yankees’ bullpen.

Yankees 2026 Roster Report Cards: Jake Bird

Jake Bird earns an F in the Yankees' 2026 roster report card after a disastrous season. Acquired at the 2025 trade deadline to bolster the bullpen, Bird gave up a debut grand slam, saw multiple early exits and posted a 5.93 ERA over 30.1 innings, with a 0.1 fWAR rating. He briefly rebounded to a 2.91 ERA in a 21.2‑inning stretch, but a July 19 collapse against the Dodgers sealed his fate. The Yankees demoted and eventually traded him to the Nationals on Aug. 2, receiving slugger Luis García Jr., who helped New York clinch a postseason spot. Bird’s high spin rates and movement never translated to consistency in New York, making his tenure a clear bust.

Yankees October Approval Poll: Brian Cashman

Pinstripe Alley’s final GM approval poll for 2026 reviews the New York Yankees’ roller‑coaster season under GM Brian Cashman. After a 7‑1 start and a brief return to the AL East lead, the team slumped when Aaron Judge fractured a rib and missed three months, causing the offense to sputter. Cashman’s approval fell to a low 9% in June, modestly rising to 34% by September as the Yankees surged to the AL’s best record in the final month, aided by Luis García Jr., and prospects George Lombard Jr. and Spencer Jones. The poll caps off with the Yankees being swept by the Rays in the ALDS, setting up a busy November before the Dec. 2 lockout.

Today on Pinstripe Alley – 11/2/26

The latest Pinstripe Alley post previews the first full week of the 2026 MLB offseason, noting upcoming awards voting, early roster moves by teams like the Giants, and a GM approval poll for November—the first since the Yankees fell in the ALDS. It also features a grade for Jake Bird’s season, a birthday tribute to Jonathan Loáisiga, an offseason mailbag invitation, and Jeremy’s BBWAA award finalists. Readers are invited to weigh in on which Yankees free agents might return and react to Cody Belinger’s Gold Glove surprise.

Yankees news: The Bombers look for help as free agency opens

Free agency opens today and the Yankees are scouting the class for postseason help. The standout target is third‑baseman Teruaki Sato, posted by Japan’s Hanshin Tigers after winning the 2025 Central League MVP and a 2026 Triple Crown (.306, 39 HR, 106 RBI). Yankees also celebrate Cody Bellinger’s Gold Glove in left field and Double‑A pitcher Cade Smith’s minor‑league Gold Glove. The roundup hints at roster moves while noting outfielder Spencer Jones’s recent engagement, but the focus remains on potential upgrades ahead of 2027.

Cody Bellinger wins 2026 Gold Glove Award

Cody Bellinger clinches his second Gold Glove, this time as the New York Yankees' left‑field standout, after tying for third most Defensive Runs Saved (21) in MLB and posting elite arm strength (93.3 mph, 94th percentile) and range (91st percentile) at Yankee Stadium. The award marks his first Gold Glove since the 2019 Dodgers MVP season, and he was the only Yankee to win among three finalists – catcher Austin Wells and utility man José Caballero fell short. The 2026 Gold Glove roster also includes notable winners such as Tanner Bibee, Christian Walker and Nolan McLean.

Yankees Social Media Spotlight: Halloween Edition

Pinstripe Alley’s Halloween roundup highlights Yankees’ social-media moments as the 2026 season wraps. While Gary Sánchez and the Brewers clinch the NL title, the Yankees celebrate with spooky Instagram posts, Spencer Jones’s Empire State Building engagement, and former Yankee Shane Greene’s career reflection. Pitcher Will Warren hints at winter training plans, CC Sabathia enjoys Brewers’ championship run, and Clarke Schmidt shares a family fishing trip. The post also notes David Cone receiving the 2026 Curt Flood Award and the Somerset Patriots honoring former Yankee Cam Schlittler’s Cy Young performance.

The Yankees Birthday Series, presented by Pinstripe Alley

Pinstripe Alley launches the Yankees Birthday Series, a daily 2026 feature spotlighting a Yankees player whose birthday falls on each calendar day. After wrapping a three‑year diary of the 1998‑2000 dynasty, the blog will now honor legends and obscure figures alike—from Charlie Devens on Jan. 1 to Aaron Judge on Apr. 26—sharing bite‑size histories and anecdotes. Readers can expect a mix of Hall‑of‑Famers, recent stars, and forgotten contributors, making every day a chance to revisit New York’s rich baseball heritage.

The most impactful plays of the 2026 Yankees’ season

Pinstripe Alley breaks down the 2026 Yankees’ season by Win Probability Added, highlighting the most game‑changing moments. The top positive plays are José Caballero’s walk‑off double on April 15 vs. the Angels (+0.663 WPA), Jazz Chisholm Jr.’s ninth‑inning go‑ahead homer on July 10 at Washington (+0.645 WPA), and Amed Rosario’s eighth‑inning, two‑run shot on April 7 vs. Oakland (+0.526 WPA). On the flip side, the worst swings include Coby Mayo’s go‑ahead homer for Baltimore on May 11 (‑0.481 WPA) and Tyrone Taylor’s game‑tying blast against New York on May 17 (‑0.483 WPA). The article pairs these stats with vivid game recaps, letting fans see which memories match the data.

Yankees Birthday of the Day: Masahiro Tanaka

On his birthday, Nov. 1, the Yankees celebrate former ace Masahiro Tanaka. The 25‑year‑old Japanese star inked a seven‑year, $155 million deal in Jan. 2014 after a stellar 2013 NPB season (1.27 ERA, 24‑0 record). He debuted on April 4, 2014, and quickly earned an All‑Star nod, posting a 2.10 ERA through his first 16 starts and recording three complete games, including a Subway Series shutout on May 14. An elbow injury in July 2014 sidelined him, but he returned without surgery. Tanaka served as the Yankees’ ace from 2015‑20, posting a career‑best 4.7 fWAR in 2016 and delivering clutch performances in the 2015 Wild Card Game and the 2017 ALDS. He retired with a reputation as a big‑game pitcher.