The first major checkpoint arrived Thursday, Oct. 29, at 9:00 a.m. ET with the official launch of free agency and the opening of the five-day exclusive negotiating window. For front offices in the Bronx, Queens, and South Philly, that ticking clock presents an immediate chance to lock down key internal pieces before outside suitors enter the fold.

Here is a complete look at the pivotal dates, deadlines, and milestones defining the 2026–27 MLB offseason:

• October 29, 2026: Free agency officially begins; five-day exclusive negotiating window opens (9:00 a.m. ET)
• November 1, 2026: Rawlings Gold Glove Award winners announced
• November 2, 2026 (5:00 p.m. ET): Open free agency begins; players are cleared to sign with any club
• November 9–12, 2026: MLB General Managers Meetings in Las Vegas
• November 9, 2026: BBWAA Jackie Robinson Rookie of the Year Award winners announced
• November 10, 2026: BBWAA Manager of the Year Award winners announced
• November 11, 2026: BBWAA Cy Young Award winners announced; All-MLB Teams revealed
• November 12, 2026: BBWAA Most Valuable Player Award winners announced
• November 12, 2026 (4:00 p.m. ET): Deadline for free agents to accept or reject qualifying offers
• November 17, 2026: Louisville Slugger Silver Slugger Award winners announced; Rule 5 Draft roster protection deadline
• November 20, 2026: Non-tender deadline (cutoff to tender contracts to arbitration-eligible and pre-arbitration players)
• December 1, 2026 (11:59 p.m. ET): MLB Collective Bargaining Agreement (CBA) expiration date
• December 7–10, 2026: MLB Winter Meetings (featuring the MLB Draft Lottery on Dec. 9 and Rule 5 Draft on Dec. 10)
• December 15, 2026: 2026 international amateur signing period officially closes

How the Yankees, Mets, and Phillies can capitalize on the winter calendar

During the five-day quiet period, the Yankees will explore extending their own impending free agents before an open market bidding war erupts. With late-inning arms like closer David Bednar and southpaw Ryan Yarbrough slated to hit the open market, all eyes turn to general manager Brian Cashman to see if the Bronx Bombers will lock them down early or risk seeing them test the waters.

In Queens, the initial five-day window serves as an opportune moment for the Mets to sort out Bo Bichette’s contract status and gauge their infield blueprints heading into next year. Down the turnpike, the Phillies face an immediate reckoning in their infield, with longtime third baseman Alec Bohm and trade-deadline acquisition Luis Arraez hitting the open market, leaving front office to decide between aggressive reunions or allowing both to walk.

Once the market fully opens on Nov. 2, industry buzz suggests a cross-town arms race could ignite over Japanese slugger Teruaki Sato, who has reportedly drawn strong interest from both the Yankees and Mets. For the Mets, speculation also continues to swirl around ace Tarik Skubal, whose prospective arrival in the Big Apple could dominate headline space once unrestricted bidding goes live.

Come December, the Phillies could shift their strategic focus toward clearing an everyday runway for elite farmhands Aidan Miller and Justin Crawford. The Winter Meetings in particular will force Philadelphia’s brass to choose between signing veteran stopgaps or handing everyday big-league roles to their prized prospects.

Key takeaways

• MLB free agency officially launched Thursday, Oct. 29, at 9:00 a.m. ET.
• The MLB Collective Bargaining Agreement expires on December 1, 2026.
• MLB open free agency begins on November 2, 2026 (5:00 p.m. ET).

Clarity may be arriving soon. According to The New York Post‘s Dan Martin, Bichette is expected to exercise his $42 million player option to remain in Queens. Per MLB rules, the two-time All-Star will have a five-day window following the conclusion of the World Series to make that decision official.

Bichette’s future was shrouded in trade and opt-out rumors following an underwhelming, injury-marred campaign. Yet opting in cements his place in New York, giving both player and team an immediate opportunity at a collective reset in 2027.

His return adds another layer to an ambitious offseason. With president of baseball operations David Stearns aggressively pursuing Japanese slugger Teruaki Sato after scouting him in person, the Mets’ offensive blueprint for next year is rapidly taking shape.

How Andy Green can balance Bichette and incoming talent

With Bichette poised to re-anchor the infield alongside Francisco Lindor, manager Andy Green must maximize his value by establishing defensive clarity while utilizing his contact-heavy bat in the heart of the order. Green’s challenge will be managing Bichette across various infield assignments—whether at second base, third base, or designated hitter—without letting defensive instability bleed into his rhythm in the batter’s box.

Green’s prior stint as the Mets’ Senior Vice President of Player Development serves as a massive asset here. Having directly overseen the organization’s farm system, Green steps into the dugout already intimately familiar with the mechanics, tendencies, and routines of premier prospects like Jefferson Rojas, significantly flattening their learning curves upon arrival.

To successfully integrate arriving youth alongside established stars, Green will need proactive platoon strategies and scripted rest days rather than reactive benchings. Creatively rotating the designated hitter slot will ensure top prospects receive consistent plate appearances without alienating core veterans or compromising late-inning defense.

Key takeaways

• Bo Bichette is expected to exercise his $42 million player option with the Mets.
• David Stearns scouted Teruaki Sato in person while aggressively pursuing the Japanese slugger.
• The two-time All-Star will have a five-day window following the conclusion of the World Series to make that decision official.

According to SNY’s Chelsea Jones, Stearns hopped on a flight to Japan to scout Sato in person immediately after the Mets’ campaign concluded. “Don’t rule out Teruaki Sato as a big addition. Stearns went to see him in Japan firsthand as soon as the Mets’ season ended. You don’t make that trip if you aren’t seriously considering making a push for him,” Jones reported regarding the front-office head’s overseas trip.

Coupled with persistent buzz linking the Mets to Tarik Skubal following his stint with the Los Angeles Dodgers, anticipation is mounting in Queens for aggressive offseason moves as the franchise looks to reassert itself as an NL contender.

Meanwhile, after acquiring Freddy Peralta midway through the season, the right-hander recently opened up about his brief tenure in Flushing, reflecting on his Mets stint before being dealt to the Tampa Bay Rays for their World Series run.

Other targets on the Mets’ winter radar

To reinforce the starting rotation beyond top-tier aces, reports indicate the Mets are eyeing established, dependable arms via free agency and the trade block. Front-office discussions have circled durable veteran options such as Matthew Boyd, alongside trade inquiries for controllable starters like Joe Ryan and Reid Detmers.

At first base and designated hitter, Stearns is exploring multiple avenues to add punch and lengthen the lineup. Breakout slugger Jake Bauers has emerged as an intriguing target on the market, while veteran bats like Ty France and perennial Gold Glover Paul Goldschmidt remain on New York’s radar as potential short-term stabilizers.

In the bullpen, the Mets are reportedly prioritizing late-inning swing-and-miss depth to complement closer Devin Williams. Reliable high-leverage arms like right-hander Evan Phillips and southpaw Alex Vesia have surfaced on the club’s wish list to fortify the relief corps ahead of 2027.

Key takeaways

• David Stearns scouted Teruaki Sato in Japan for the New York Mets.
• Tarik Skubal was linked to the New York Mets following his Dodgers stint.
• The New York Mets are reportedly prioritizing late-inning swing-and-miss depth to complement closer Devin Williams.

“If the Mets sign Skubal and still need to add, I could see them pursuing a similar deal to the one they made for Peralta this year, plucking a proven guy about to hit free agency away from a team that will not pay him,” Janes revealed.

Several names are being linked to the Mets, some of whom are still competing this season. While there is no clarity on the negotiations, the insider indicated that the team will be targeting an established player.

“Joe Ryan from Minnesota, Nick Martinez (big mutual option in Tampa), Drew Rasmussen (also potentially big option in Tampa), George Kirby and others fit this profile,” Janes added. “But I think even if Skubal signs, another biggish-name starter could still be on the way.”

Stearns sets his sights on an international star

One name generating significant buzz as a potential MLB arrival next season is coming from Japan. While Teruaki Sato is reportedly in line for a big deal with the New York Yankees, David Stearns traveled all the way to Asia to see the Japanese infielder’s talent firsthand.

“You don’t make that trip if you aren’t seriously considering making a push for him,” Chelsea Janes wrote on X. The Los Angeles Angels, Boston Red Sox, and Philadelphia Phillies are the other three teams keeping an eye on Sato, making it clear that this player could be on the move in the near future.

A fresh start in Queens

The Mets are eager to hit the reset button after a deeply frustrating 2026 campaign. Queens was hit with a brutal reality check as the team plummeted to a last-place 74-88 finish in the NL East, missing out on October baseball entirely.

After parting ways with Carlos Mendoza mid-season, the Mets front office decided on long-term stability by officially naming interim skipper Andy Green as their full-time manager for 2027 and beyond. With Steve Cohen and David Stearns locked in to retool the roster around Juan Soto and Bo Bichette, Green’s mission next year will be turning around the clubhouse culture and translating massive payroll potential into actual wins.

Key takeaways

• SNY’s Chelsea Janes reported the New York Mets are considering acquiring pitcher Tarik Skubal.
• David Stearns traveled to Asia to evaluate Japanese infielder Teruaki Sato in person.
• The Mets named Andy Green as their full-time manager for 2027.

“I was feeling bad because I couldn’t do anything for them when they had a lot of big expectations for me, the fans too in New York. They were waiting for something great from me,” Peralta revealed recently during a press conference.

Eventually, a trade seemed inevitable given the delicate situation he was facing. “I’ve been in this business for a long time now and I understand how it works. I knew it was best for the Mets organization to trade me and get something for me.”

For Peralta, the outcome of this saga turned out to be far more promising. Today, he finds himself competing for a championship with the Rays, while the Metropolitans quickly fell short of their goals.

His physical performance wasn’t the problem

A decline in performance among MLB players can be attributed to various factors, including their physical condition. In Freddy Peralta’s case, however, his physical fitness was not a limiting factor in his failure to perform at his best with the Mets.

“I was feeling really good physically. I was trying to give the best of myself as always and I prepared how I should be preparing. I don’t know, things weren’t going my way.”

A promising outlook that never materialized

Brought in as a marquee rotation arm, Freddy Peralta stumbled through his first 22 starts with Queens, posting a brutal 5.33 ERA, a sky-high 1.33 WHIP, and generating negative bWAR while battling command issues and a noticeable drop in fastball velocity. A sluggish arm slot and poor fit with New York’s pitching staff crippled his horizontal pitch movement, causing opposing hitters to crush him for a .311 BABIP and leaving the Mets with no choice but to sell low on his contract.

Key takeaways

• Freddy Peralta admitted feeling bad for failing to meet expectations with the Mets.
• Freddy Peralta stated that his physical condition was not the reason for his struggles.
• Freddy Peralta recorded a brutal 5.33 ERA through 22 starts with the Mets.

Phillies president of baseball operations Dave Dombrowski announced that the club has hired Mendoza as its new third base and infield coach, as first cited by SNY.

The move marks the start of a coaching staff overhaul in Philadelphia following a disappointing postseason exit. With buzz building around the potential hiring of Don Mattingly as the Phillies’ next manager, a ripple effect of key roster decisions is expected to follow.

Among those pressing decisions is addressing impending free agents—including left-hander Luis Arraez—alongside evaluating several underperforming veterans on the 2026 roster.

Mendoza’s experience as third base coach

Before taking the top job in Queens, Mendoza spent 15 years building a reputation across Major League organizations as an elite infield coordinator and bench strategist. His coaching foundation was forged in player development, spending nearly a decade in the New York Yankees farm system as a roving defensive instructor and minor league manager.

That minor league success propelled him to the Bronx, where he served on the Yankees’ Major League staff from 2018 through 2023 as a quality control coach, infield instructor, and ultimately as Aaron Boone’s bench coach for four seasons.

Throughout his time in New York, Mendoza was directly responsible for designing daily infield routines, crafting positioning strategies, and managing in-game defensive alignments, earning league-wide respect for his tactical preparation.

Why did the Mets let Mendoza leave?

Mendoza took over as manager of the Mets prior to the 2024 season, immediately making a splash by leading the club to an unexpected NLCS run. However, after a regression during the 2025 season and a slow start in 2026, New York decided to move in a different direction midyear.

By bringing Mendoza aboard, the Phillies land a proven baseball mind with a deep divisional track record. His primary focus in Philadelphia will be sharpening the team’s infield defense and overseeing third-base coaching duties.

Key takeaways

• Carlos Mendoza was hired by the Philadelphia Phillies as third base and infield coach.
• Don Mattingly is expected to be announced as Philadelphia’s new manager.
• Mendoza served as Aaron Boone’s bench coach for four seasons with the Yankees.

And in the City That Never Sleeps, the two organizations are wide awake, daydreaming of the day they will go all the way again. That’s a road that could very well lead them to hand Skubal the piggy-bank-shattering contract he’s after, which he’ll surely get before the 2027 MLB campaign.

According to a report, if it comes down to a three-horse race between the Dodgers, Yankees, and Mets—and it very well could—the latter may have the upper hand. The Orange and Blue are the most desperate of the bunch, which is saying a lot, and that could make David Stearns and Steve Cohen sign on the dotted line for a contract that can make the hairs on Skubal’s right arm stand up.

“The Skubal sweepstakes could come down to which of the Mets, Dodgers or Yankees would be most willing to take the risk. And of those three clubs, the Mets may have the clearest need for a No. 1 starter this winter,” Zachary D. Rymer of Bleacher Report stated.

Skubal’s contract projections

“The average projected contract was eight years and $355 million, which is a $44.6 million average annual value (AAV),” Kiley McDaniel of ESPN reported on the situation as the MLB landscape gears up for a roller-coaster of an offseason, with Skubal’s future sitting in the front row.

The Mets already have the highest payroll in all of MLB and could be looking to add yet another ginormous contract to the mix. To say they will be in a World Series-or-bust year would be an understatement.

However, considering they just missed the playoffs and seem fine with making no drastic changes to their brass, we may actually be wrong to assume the organization is placing such expectations on itself. Maybe they’re only saying that publicly without holding themselves to the same standard behind closed doors.

NY Mets could make — another — splash

A lot can be said about the Mets’ deficiencies and shortcomings, but there is no doubt about their willingness to spend, especially when they’re competing against the Yankees and Dodgers in a bidding war. In the winter of 2026-27, fans across MLB may see another historic spending battle between these three teams for the best pitcher available: Tarik Skubal.

Key takeaways

• The New York Mets may have the clearest need for a starting pitcher among interested suitors.
• Tarik Skubal is projected to receive an eight-year, $355 million contract in free agency.
• The New York Mets maintain the highest payroll across all of Major League Baseball.

“Being a manager in Major League Baseball is a huge commitment, very huge commitment,” Beltran told reporters. “I’m not saying that I’m not willing to take that commitment, but right now, at the position where I am today in life, I love to be a dad. I love to be a husband. I love to be involved in the Carlos Beltran Baseball Academy in Puerto Rico. Being a manager, you would not be able to do that full-time.”

Beltran’s comments signal that his current priorities lie outside the dugout, leaving the door open for other potential candidates as the Mets evaluate their managerial options for 2027.

In the meantime, the Mets are fighting to avoid a last-place finish in the NL East during the final stretch of the 2026 season, encouraged slightly by positive medical updates regarding outfielder Jared Young.

Reported candidates in the mix for managerial job

Even with Beltran occasionally linked to the opening, President of Baseball Operations David Stearns and team leadership are casting a wide net to find the right fit for the franchise.

Several high-profile candidates have emerged in national reporting:

• Alex Cora: Frequently cited by MLB insiders as a primary target if he becomes available.
• Albert Pujols: The future Hall of Famer has been widely reported as a candidate ownership and David Stearns are eager to speak with.
• David Ross: The former Chicago Cubs manager publicly stated on ESPN that he would be interested in interviewing for the position.
• Rocco Baldelli: The former Minnesota Twins skipper has been identified by national reporters as an experienced candidate who could provide stability.
• Don Mattingly / Rob Thomson: Veteran names linked speculatively depending on how managerial openings unfold across the league this offseason.

With only a week remaining in the regular season, the Mets face a crucial offseason as they look to reshape their leadership and position the franchise for a bounce-back campaign in 2027.

Providing a much-needed sigh of relief, manager Andy Green offered an encouraging update on Young’s recovery during a recent press conference, noting that the infielder is in remarkably high spirits. “Young is doing as good as expected or could be hoped for. He’s got his sense of humor intact,” Green said.

The severity of the collision brought the game to a standstill—drawing heartfelt well-wishes from Phillies superstar Bryce Harper—and left the entire organization holding its breath as New York looks to navigate the final stretch of the regular season without one of its most key contributors.

Despite the encouraging update, the strict timeline required by MLB’s concussion protocol makes a swift return improbable, leaving Young’s availability up in the air with just over a week remaining before the postseason.

Green shares a story from Young’s time with the Reds

Reflecting on Young’s tireless work ethic, Green shared an anecdote from their shared time with the Cincinnati Reds, illustrating the 31-year-old’s unyielding passion for the game.

“This guy likes to play so much. He said, ‘Can I drive to Iowa and play?’ I told him, ‘If you want to, but your season could be over.’ I’ve never had a player do that in that situation. Most guys are like, ‘I’m getting optioned from the big leagues, let’s call it a season, let’s move on. It’s good enough,’“ Green recalled.

“Instead, he texted the Triple-A manager and said, ‘I’m coming. I want to play. Can you put me in the lineup?’ He ended up hitting a walk-off home run that day to cap off the minor league season,“ Green added.

Young’s impact on the Mets

Serving primarily as a versatile option at first base, outfield, and designated hitter, the left-handed slugger provided crucial depth above league average, slashing .266 with 9 home runs, 39 RBIs, and a .759 OPS (112 OPS+) across 308 at-bats (342 plate appearances).

According to the New York Post‘s Jon Heyman, league insiders remain split on whether Bichette will opt out or choose to stay in Queens, setting up a defining offseason decision for both sides.

Bichette’s debut season in New York has been a true rollercoaster. Plagued by injuries and lingering slumps, the former All-Star shortstop has struggled to replicate his past production while adjusting to his new defensive home at third base.

The Mets’ late-season slide hasn’t sat well with starter Sean Manaea, who openly vented after home fans cheered former Mets slugger Pete Alonso during his return with the Baltimore Orioles. If Bichette decides to walk this winter, it will leave the front office scrambling to fill another major hole in the lineup.

Bichette’s rollercoaster season in Queens

From an alarming early-season slump to a midsummer rebound, Bichette’s performance has left the Mets‘ front office closely monitoring his upcoming contract status, a decision that will heavily influence the organization’s offseason blueprint.

After joining the Mets on a three-year deal during the 2025–26 offseason, Bichette endured a grueling first two months. His early cold spell dragged down his overall offensive numbers while putting added pressure on his full-time transition to third base.

A midseason resurgence helped stabilize his contact profile, raising his batting average back toward the .265 mark and providing much-needed middle-of-the-order run production.

Bichette’s stats in the Mets this season:

• 151 games
• .263 AVG
• .312 OBP
• .390 SLG
• .702 OPS
• 16 HR
• 74 RBI

The opt-out dilemma

With $84 million remaining over the final two years of his contract, Bichette holds an opt-out clause at season’s end. Industry insiders view his impending choice as a true toss-up: weigh the guaranteed security of $42 million annually in New York against testing a thin free-agent market entering his age-29 season.

“First of all, I hope Jared Young is OK. I’m sending my thoughts to his family and hoping for the best,” Harper told Ken Rosenthal on the MLB on FOX broadcast, a gesture that drew widespread praise from both fanbases.

Harper and the Phillies ultimately secured the win in a game that won’t soon be forgotten given the harrowing situation with Young. For New York, the loss serves as another stark wake-up call as they continue to slide toward the bottom of the standings.

While Mets pitcher Sean Manaea didn’t hide his emotions regarding fans showing support for former slugger Pete Alonso—now with the Baltimore Orioles—the franchise is dealing with a far more immediate setback in Young, who had been working to regain his stride after early-season struggles.

What happened to Young?

In the top of the sixth inning, Phillies outfielder Justin Crawford hit a ground ball toward first base. As Mets starting pitcher Nolan McLean sprinted over to cover the bag, his leg inadvertently made direct contact with Young’s head while the first baseman was bending down to field the ball.

Young was knocked unconscious by the impact and remained on the turf while being evaluated by trainers before being carted off the field. He was transported to a local hospital for further diagnostic testing and evaluation.

Young’s status pending medical official diagnosis

The Mets confirmed that Young retained movement and feeling in all of his extremities. Manager Andy Green later shared that Young’s CT scan came back negative for structural damage, but he is exhibiting concussion symptoms and has been placed in MLB’s concussion protocol.

The injury leaves Young’s status uncertain just as he was beginning to show signs of a turnaround this season, a welcome bounce-back after a difficult 2025 campaign following his arrival from the Chicago White Sox.