Pinstripe Alley
Gary Good, Gleyber Good
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Yankees 2026 Roster Report Cards: Tim Hill
Tim Hill’s two‑year Yankees stint began as a bullpen gem, posting a 2.48 ERA, a league‑best 68.3% ground‑ball rate and 128 appearances from June 2024 to May 2026. The left‑hander’s 2025 line showed a 4.60 ERA and -1.1 fWAR, and a disastrous May 22, 2026 outing against the Rays saw his ERA balloon to 6.23, his ground‑ball rate halve and 11 homers surrender. Manager Aaron Boone left him off the Wild Card and ALDS rosters, opting for Ryan Yarbrough instead. Now a free agent at 36, Hill’s future hinges on whether teams believe he can recapture his elite sinker‑induced ground balls.
Today on Pinstripe Alley – 10/26/26
The World Series shifts to Tropicana Field for Game 3 as the Milwaukee Brewers lead the Tampa Bay Rays 2-0. Freddy Peralta, fresh off an ALCS MVP award after his trade from the Mets, will start for the Rays against Brewers left‑hander Robert Gasser at 8 p.m. EST on FOX. The post also previews Nick’s review of Tim Hill’s underwhelming 2026 season and a profile of obscure Yankee Snuffy Sternweiss. Fans debate the pitching edge and Peralta’s rising free‑agent value after his postseason surge.
Yankees news: Not buying what the Yanks were selling
Pinstripe Alley highlights the fallout from the Yankees' early October exit, with Erik Boland lambasting Hal Steinbrenner, Brian Cashman and Aaron Boone for blaming players while dismissing deeper organizational issues. The piece also cites MLB Trade Rumors on catcher Austin Wells, suggesting the Yanks might pursue Tyler Stephenson, Ryan Jeffers or a trade for Hunter Goodman depending on Wells' performance trajectory. NJ.com notes the club will shed $71.9 million in payroll, but potential raises and guarantees for David Bednar and Paul Blackburn could consume $35 million, prompting further non‑tender moves.
Yankees Social Media Spotlight: The MA kids head to MSG
The Pinstripe Alley roundup recaps the Yankees’ off‑season social buzz. Yankees prospects Cam Schlittler and Ben Rice attend the Knicks’ championship‑ring ceremony at Madison Square Garden, where the 2026 NBA champs raise a banner before losing to the 76ers. Former infielders Gleyber Torres and Gio Urshela are spotted vacationing in Europe, while the Somerset Patriots celebrate rookie shortstop George Lombard Jr.'s season totals. Prospects Luke Pettitte’s wedding gets a family Instagram shout‑out, and Brendan Beck reflects on his MLB debut and Triple‑A success. Finally, the Scranton RailRiders host a yard sale on Nov 1.
What if the Yankees could amnesty a contract?
Pinstripe Alley explores a hypothetical amnesty move for the Yankees after their $313 million 2026 payroll. While long‑term deals on Gerrit Cole, Giancarlo Stanton and others are mostly near expiration, the piece narrows the candidates to Stanton and third‑baseman Ryan McMahon. Stanton’s 2027 contract costs the Yankees a minimum of $15 million (with a $22 million luxury‑tax hit) and includes a $25 million team option, yet he spent most of 2026 on the IL. McMahon’s final‑year deal is $16 million with modest on‑field value. The analysis concludes that amnestying Stanton offers the biggest financial relief and roster flexibility, making him the clear target.
The Yankees Birthday Series, presented by Pinstripe Alley
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 […]
Yankees Birthday of the Day: Bobby Brown
On October 25, the Pinstripe Alley birthday series honors former Yankee infielder Bobby Brown (1924-2021). A Stanford graduate and Navy veteran, Brown debuted with New York in 1946, posting a .341 minor‑league average and a seven‑game MLB cameo. He became a key pinch‑hitter in the 1947 World Series, delivering an RBI double in Game 7 that helped the Yankees beat the Dodgers 5‑2. Brown later anchored third base, winning four World Series rings and posting a .439 career World Series slash line. After serving as a doctor in the Korean War, he briefly returned in 1954 before retiring to medicine, later serving as interim Texas Rangers president (1974) and as American League president (1984‑1994).
Avenging the 2026 Yankees on MLB The Show 26
In a playful MLB The Show 26 experiment, Pinstripe Alley’s author retools the 2026 Yankees to see what it would take for them to finally win a World Series. By swapping Junior Caminero to third base and later adding AL MVP hopeful Yordan Alvarez, the virtual Yankees post a 91‑71 record, clinch the AL East, and battle past the Blue Jays, Mariners and Cubs to claim the title—thanks to a walk‑off hit by Austin Wells and a solid postseason from Alvarez. The simulation also shows the impact of injuries to Gerrit Cole, Carlos Rodón and Caminero, and ends with Cody Bellinger earning WS MVP. The piece blends real‑season frustration with a detailed video‑game scenario for readers curious about the Yankees’ missing pieces.
Playoff Roundup: Brewers rally to take 2-0 lead in World Series
The Milwaukee Brewers rally from a 4-0 first‑inning deficit to beat the Tampa Bay Rays 5‑4 in Game 2 of the 2026 World Series, seizing a 2‑0 series lead. After Rays rookie ace Drew Rasmussen sparks the early lead with a solo homer by Liam Hicks, Milwaukee chips away with timely hits from Jackson Chourio, Jake Bauers, William Contreras and Garrett Mitchell. Sal Frelick’s sixth‑inning solo blast and a decisive seventh‑inning double by Brice Turang set up the go‑ahead run. The Rays’ final chance ends on a disputed strike‑three to Yandy Díaz, cementing the comeback and placing the Brewers in rare MLB history company.
Today on Pinstripe Alley – 10/25/26
Game 2 of the 2026 World Series sees the Milwaukee Brewers rally from a 4-0 deficit to beat the Tampa Bay Rays 2-0, taking a 2-0 series lead at American Family Field. Highlighting ace Drew Rasmussen’s start for the Rays and the Brewers’ trademark comeback, the post previews the upcoming Game 3 in Tampa, where the Rays’ strong home record could tighten the contest. It also teases in‑depth analysis by Matt on the game, a gaming segment, a profile of Bobby Brown, a Yankees roster contract discussion, and a social media roundup.
Yankees news: Three-year extension confirmed for pitching coach Matt Blake
The Yankees lock up pitching coach Matt Blake on a three‑year extension, cementing the architect behind the league‑best 3.23 ERA. Blake’s work with ace Gerrit Cole, Cy Young hopeful Cam Schlittler and reliever conversions like Brent Headrick and Paul Blackburn is credited for the staff’s success. While Blake stays, Triple‑A coach Spencer Medick departs for the Astros as their director of pitching, highlighting a shift in the organization’s developmental pipeline. The move signals NY’s confidence in its pitching factory heading into the offseason.
Today on Pinstripe Alley – 10/24/26
The Brewers clinch a 3-2 win over the Rays in Game 1 of the 2026 World Series at American Family Field, delivering Milwaukee its first World Series victory in 44 years. Pitching duels feature Jacob Misiorowski vs. Nick Martinez and a standout start by Drew Rasmussen, while Logan Henderson receives a nod despite the loss. The post also previews Game 2 (Brewers lead 1-0), outlines upcoming site content on Yankees prospects, the Deadball Era, and financial analysis, and invites fan discussion on the Game 1 MVP and a controversial replay overturn in the ninth inning.
Hal Steinbrenner’s lack of self-examination is not a good sign for the Yankees
The Yankees’ 2026 ALDS sweep by the Tampa Bay Rays has sparked criticism of chairman Hal Steinbrenner, who blamed the team’s offensive woes on the players rather than manager Aaron Boone or GM Brian Cashman. The piece argues that Steinbrenner’s refusal to self‑examine is misplaced, citing poor performances from Austin Wells, Jazz Chisholm Jr., Ryan McMahon, Anthony Volpe and a disastrous leadoff stint by Trent Grisham. It notes the Yankees’ 27‑30 playoff record under Boone and Cashman since 2018 and highlights deeper issues in roster construction, scouting and hitting development that could doom future October runs.
Yankees reportedly extend Matt Blake with three-year deal
The New York Yankees have locked pitching coach Matt Blake into a three‑year extension, according to the New York Post. Blake, who joined the staff in 2020, helped the Yankees post the league‑best 3.23 ERA, a 3.71 FIP (third) and a franchise‑high 21.9 fWAR this season, with Cam Schlitter emerging as a presumptive Cy Young candidate. His work developing lesser‑known starters like Will Warren and Ryan Weathers, plus relievers Paul Blackburn, Brent Headrick and David Bednar, is credited for the staff’s depth despite injuries to Gerrit Cole, Max Fried and Carlos Rodón. The extension secures one of Aaron Boone’s few remaining coaching assets as the Yankees chase a 28th World Series title.
Where the Yankees’ budget stands as the offseason begins
As the 2026 World Series winds down, Pinstripe Alley breaks down the Yankees’ payroll heading into the offseason. Seven players—including three starters—carry a $212.4 million luxury‑tax hit for 2027, a sum larger than 19 teams’ entire payrolls. Yet only three contracts (Aaron Judge, Cody Bellinger, Max Fried) run past 2028, and the club clears dead money with Aaron Hicks and DJ LeMahieu now off the books. Nine arbitration‑eligible players could earn $2.3‑$11 million each, while pre‑arbitration salaries sit between $1‑$1.5 million under competing CBA proposals. Overall, the Yankees’ 2027 luxury‑tax payroll is projected at $265‑$273 million—$40‑$50 million lower than 2026—leaving significant financial flexibility amid uncertain CBA talks.
Yankees Birthday of the Day: Hugh High
On October 24, 2026 Pinstripe Alley honors Yankees outfielder Hugh High, born 1887, who helped lift the franchise from its early‑century woes. After the Tigers sold High and future star Wally Pipp to New York in 1914, High became a regular in 1915, posting a career‑high 119 games, 27 extra‑base hits and 22 steals. He contributed to the Yankees’ first winning season in 1916 alongside Hall of Famer Frank “Home Run” Baker, but injuries and illness derailed his career. By 1918 the team tried to trade him, he refused, and left baseball for a shipyard job. The piece blends stats, anecdotes and historic context.
Yankees Arizona Fall League Week 3 Recap
Yankees prospects spark Salt River Rafters’ 9‑7 record in AFL Week 3. Dax Kilby leads the charge, logging a 2‑for‑4 night with a 107 mph, 410‑ft homer and a 109.8 mph RBI double on Oct. 19, then adding a triple and two stolen bases. Core Jackson contributes a 421‑ft, 105 mph blast and a triple, while Kyle West adds a 104.9 mph single. The Rafters win four of five games (5‑0, 7‑1, 10‑11, 7‑5) before a 15‑8 loss. Pitching highlights include JT Etheridge’s 6 IP, 9 K and Antonio Gomez’s scoreless eighth. The team sits a half‑game from a first‑round bye heading into the postseason.
Playoff Roundup: Misiorowski, Yelich strike early in Brewers’ Game 1 win
The Brewers edge the Rays 3-2 in World Series Game 1, taking a 1-0 series lead. Jacob Misiorowski pitches five solid innings, allowing just two runs despite a postseason dip in strikeout rate, while Aaron Ashby and Trevor Megill close the final 2.2 frames. Early offense erupts as Christian Yelich belts an RBI triple off Nick Martinez and William Contreras follows with a two-run single, giving Milwaukee a 2-0 cushion. Tampa Bay rallies in the fourth, cutting the lead to one, but a failed steal and Contreras’s sharp throw preserve the win. Milwaukee’s blend of starter endurance, middle‑inning groundball work, and late‑relief firepower proves decisive.
Today on Pinstripe Alley – 10/24/26
The Milwaukee Brewers edge the Tampa Bay Rays 3-2 in Game 1 of the 2026 World Series at American Family Field, snapping a 44‑year championship drought. Pitchers Jacob Misiorowski and Nick Martinez deliver a tight duel, while Drew Rasmussen shines for the Brewers in a clutch ninth inning. The post previews Game 2 (Brewers lead series 1-0), lists upcoming site recaps, and teases Yankees prospect coverage and budget analysis. It also invites reader interaction with questions about the Game 1 MVP and a controversial replay review.
Yankees news: Matt Blake expected to agree to new contract to return to Bronx
The Yankees are on the verge of re‑signing pitching coach Matt Blake, whose leadership helped shape arguably the league’s top rotation in 2026 and turned several low‑profile starters into key bullpen pieces. While the World Series begins and no roster moves have been filed yet, sources say a new contract with Blake is imminent, signaling the club’s intent to retain its coaching core ahead of offseason decisions.
Today on Pinstripe Alley – 10/23/26
The 2026 World Series kicks off tonight at American Family Field as the Tampa Bay Rays face the Milwaukee Brewers in a winner‑takes‑all clash that guarantees a franchise’s first championship. Milwaukee rolls out ace Jacob Misiorowski, while the Rays are expected to start Nick Martinez, allowing Drew Rasmussen extra rest. The blog preview includes pitching and hitting analyses, a Report Card review of Trent Grisham’s season, and a historic Yankees piece by Jonathan. Game 1 begins at 8 p.m. EST on Fox, and fans are invited to weigh in on the starter choice and pick their champion.
Yankees Mailbag: A qualifying offer conundrum
In this Pinstripe Alley mailbag, the author tackles two hot off‑season topics for the Yankees. First, they debate whether New York will extend a qualifying offer to Jazz Chisholm Jr., noting recent reports that the team may let him walk despite his market value, while also weighing the $45 million budget hit of pairing a QO with a deal for reliever Lucas Bednar. Second, they assess third‑base woes, focusing on Ryan McMahon’s disappointing 2026 season and $16 million 2027 salary, and argue that a DFA or a trade with prospects attached is more likely than a straight sale, especially as the club also eyes Giancarlo Stanton’s looming contract. The piece offers insight into the Yankees’ financial constraints and roster priorities heading into free agency.
How open is that championship window?
The article reflects on how quickly championship windows close, using the Chicago Cubs’ 2016 World Series win as a cautionary tale. It notes the Cubs’ post‑title struggles—five playoff trips, two division crowns, and the decline of stars like Kris Bryant, Anthony Rizzo and Addison Russell—while contrasting the Yankees’ near‑dynasty, highlighted by Aaron Judge’s rise and the fading of early‑2010s pieces such as Gary Sánchez. It also mentions the Red Sox’s recent success and the Brewers‑Rays matchup that opens the 2026 World Series. The piece warns that even teams with deep pockets and talent can miss out, urging fans to recognize the fleeting nature of a title run.
2026 World Series Preview: Pitching
The Pinstripe Alley preview breaks down the Brewers' pitching strengths ahead of the 2026 World Series. Milwaukee’s staff tops MLB in strikeout rate (27.4%) and K‑BB% (19.6%), ranking in the top five for ERA (3.61), FIP (3.73) and fWAR (15.6). Star rookie Jacob Misiorowski, the presumptive NL Cy Young, posted a 1.80 ERA, 252 Ks and a record‑setting 106 mph fastball, but his postseason whiff rate has dropped to 16.1% and he failed to go beyond five innings in the NLCS. Backup starter Logan Henderson (2.33 ERA) and potential Game 3 ace Robert Gasser are also discussed, while the bullpen shines with a 1.33 ERA and standout relievers Aaron Ashby and Trevor Megill.
Yankees Birthday of the Day: Birdie Cree
On October 23, Pinstripe Alley celebrates the birthday of William "Birdie" Cree, a versatile outfielder who played for the New York Highlanders/Yankees from 1908‑1915. Born in 1882 near Pittsburgh, Cree juggled teaching, football and baseball before debuting in September 1908. He posted a breakout .348 average with a .513 slugging rate in 1911, ranking among the AL’s top five in several categories, and recorded the first right‑handed home run at Shibe Park. A wrist injury in 1912 derailed his career, leading to a decline and retirement after a .292 career average. Post‑baseball, Cree worked in banking and enjoyed golf and tennis.
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