Important dates to know as Phillies enter uncertain offseason originally appeared on NBC Sports Philadelphia
Major League Baseball will enter an unorthodox offseason with an expected work stoppage that could very well impact the 2027 season.
That will directly impact the Phillies.
The organization enters the winter without a permanent manager, with several prominent players reaching free agency and with an expensive roster that needs more than a few alterations after its fifth consecutive postseason run ended without a championship.
The most significant date on the calendar is Dec. 1, when the collective bargaining agreement expires. If Major League Baseball and the Players Association do not reach a new agreement, the owners are expected to initiate a lockout.
Before then, the Phillies will have opportunities to change their roster. They will also face several deadlines that could shape what they are able to accomplish before transactions potentially come to a halt.
Here are the important dates to know:
TBD (October): Phillies’ end of season press conference
The Phillies have not announced when they will hold their end-of-season press conference.
Philadelphia could make a decision on Don Mattingly before the press conference takes place. Either way, it should provide insight into their managerial direction and how aggressively the organization intends to reshape its roster before the CBA expires.
Oct. 23-31: World Series
The World Series is scheduled to begin Oct. 23. A potential Game 7 would be played Oct. 31.
Its conclusion will officially begin the offseason transaction calendar. Several deadlines are determined by the number of days following the final game rather than a fixed date.
Day after the World Series: Free agency begins
Players with expiring contracts become free agents the day after the World Series, although they cannot sign with another organization until five days after the series ends. Teams are permitted to begin making trades immediately.
The Phillies’ impending free agents include Alec Bohm, Luis Arraez, Adolis García, Edmundo Sosa, José Alvarado, Brooks Raley and Tim Mayza.
Nestor Cortes is also set to become a free agent after signing a major-league contract with the Phillies in August.
That group represents a considerable portion of the lineup, bench and bullpen. The Phillies will have an exclusive five-day window to negotiate with them before they can sign elsewhere.
Unlike several other clubs, the Phillies do not currently have a major-league contract option to exercise or decline.
Fifth day after the World Series: Open free agency and qualifying offers
Free agents can begin signing with all 30 teams five days after the World Series ends.
This is also the deadline for clubs to extend qualifying offers to eligible free agents. Players who receive one will have 10 additional days to accept or reject it.
The Phillies will have to determine whether any of their eligible free agents warrant an offer. If a player rejects it and signs elsewhere, Philadelphia would receive draft-pick compensation. Depending on the signing club’s revenue-sharing and competitive-balance-tax status, it could forfeit draft selections and international bonus-pool money.
Players on the 60-day injured list must also be reinstated by this date, which can create an immediate 40-man roster crunch.
Nov. 1-Dec. 5: Japanese posting window
Players under contract with Nippon Professional Baseball clubs can be posted for major-league teams during this window.
Once a player is posted, teams have 45 days to negotiate a contract. If no agreement is reached, the player returns to his Japanese club.
That window carries additional interest after the Phillies’ previous attempts to sign Yoshinobu Yamamoto and Roki Sasaki. The organization has never signed a Japanese-born player to a major-league contract, but Japan could provide the Phillies with an opportunity to alter the identity of their roster.
Third baseman Teruaki Sato is among the Japanese players expected to attract major-league interest if he is posted.
Nov. 9-12: BBWAA awards announced
The major Baseball Writers’ Association of America awards will be revealed over four consecutive nights.
Rookie of the Year will be announced Nov. 9, Manager of the Year on Nov. 10, Cy Young on Nov. 11 and Most Valuable Player on Nov. 12.
The Gold Glove, Silver Slugger, All-MLB, Hank Aaron, Comeback Player of the Year and Reliever of the Year awards will also be announced during the offseason.
Nov. 14: Arizona Fall League championship
The Arizona Fall League championship will be played Nov. 14.
Ten Phillies prospects are participating in the league, including Aidan Miller, Aroon Escobar and Dante Nori. Their performances can be followed throughout the season in the Phillies’ Arizona Fall League tracker.
The Fall League gives Miller an opportunity to make up for time lost to back surgery. It also gives the Phillies a longer evaluation period for several prospects before they make their Rule 5 decisions.
Nov. 17: Rule 5 protection deadline
The Phillies must add eligible prospects to their 40-man roster by Nov. 17 to protect them from the Rule 5 draft.
Among their eligible prospects are Bryan Rincon, Aroon Escobar, Pan Wen-hui, Mavis Graves and Kehden Hettiger.
Rincon and Escobar spent the season with Double-A Reading. Both are ranked among the top prospects in the Phillies’ system and would be at risk of being selected if left unprotected.
A player selected in the major-league phase of the Rule 5 draft must remain on his new team’s active roster for the entire following season or be offered back to his original organization.
Nov. 20: Non-tender deadline
The Phillies must tender contracts to every unsigned player on their 40-man roster by Nov. 20. Any player who is not tendered a contract immediately becomes a free agent.
Philadelphia has nine players eligible for salary arbitration: Garrett Stubbs, Brandon Marsh, Jhoan Duran, Bryson Stott, Tanner Banks, Derek Hill, Rafael Marchán, Bryan De La Cruz and Orion Kerkering.
Tendering a contract does not finalize a player’s salary. It allows the Phillies to retain his rights and continue negotiating before arbitration figures are exchanged.
The deadline could create additional movement. The Phillies can trade an arbitration-eligible player before Nov. 20 or non-tender him if they do not believe his projected salary fits their plans.
Dec. 1: Collective bargaining agreement expires
The current CBA expires at 11:59 p.m. ET on Dec. 1.
If the league and union do not reach a new agreement, MLB’s owners are expected to lock out the players. Transactions involving major-league players would stop, and team officials would be prohibited from communicating with players on the 40-man roster.
That possibility adds another layer to the Phillies’ managerial decision. A new manager could have a limited period to speak with his players and establish relationships before communication is cut off.
The uncertainty also complicates long-term planning. Salary arbitration, the competitive-balance tax, free agency, revenue sharing and other roster rules could change under the next agreement. The Phillies have already committed significant money beyond 2026, while players such as Stott, Duran and Marsh are approaching increasingly expensive arbitration seasons.
It is also why early extension decisions involving Andrew Painter, Justin Crawford and Aidan Miller have become more complicated.
Dec. 7-9: Winter Meetings
The Winter Meetings are scheduled to take place in San Diego from Dec. 7-9.
Those meetings would ordinarily represent one of the busiest periods of the offseason, but they are expected to be canceled if the owners initiate a lockout.
The MLB draft lottery is scheduled for Dec. 8, followed by the Rule 5 draft on Dec. 9. The lottery would be delayed until a new agreement is reached if there is a lockout. The Rule 5 draft could be postponed or canceled entirely.
January: Arbitration and international signing period
Under a normal offseason calendar, teams and arbitration-eligible players exchange salary figures in January. Players who do not reach agreements with their clubs proceed to hearings later in the winter.
Those dates could be delayed or replaced depending on the next CBA. The Phillies’ arbitration class is especially significant because Stott, Marsh and Duran are each due sizable raises.
The international amateur signing period is also expected to open in January. The Phillies made their largest international investment in franchise history when they signed Francisco Renteria in 2025, and he has quickly developed into one of the top prospects in the organization.
That portion of the calendar could also be changed by a new agreement.
The Baseball Hall of Fame voting results will be announced in January. Chase Utley, Jimmy Rollins, Cole Hamels and Bobby Abreu are expected to return to the ballot. Utley received 59.1 percent of the vote last winter, leaving him within striking distance of the 75-percent threshold in his fourth year of eligibility.
Feb. 19: Phillies begin Grapefruit League play
The Phillies are scheduled to open their spring training schedule against the Tigers in Lakeland on Feb. 19. Their first home game in Clearwater is scheduled for the following day against the Blue Jays.
Those games remain on the calendar, but their status will depend on whether MLB and the union can complete a new agreement in time.
The previous lockout lasted 99 days and delayed the beginning of spring training in 2022.
March 25: Opening Day
The Phillies are scheduled to open the 2027 regular season against the Nationals in Washington on March 25.
Their home opener is scheduled for April 1, also against Washington.
Those dates provide the endpoint for an offseason unlike any the Phillies have faced during their current competitive window. How much business they complete before Dec. 1 could determine how prepared they are whenever baseball resumes.