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The offseason has arrived, and the Milwaukee Brewers are basking in the glow of their 2026 championship. As November begins, all 30 clubs are now focused on assembling their rosters for the 2027 campaign. Yet this winter is anything but ordinary, as the looming expiration of the Collective Bargaining Agreement (CBA) threatens to disrupt the usual flow of business. With a lockout appearing increasingly likely, teams are motivated to complete as much offseason work as possible before the December 1 CBA deadline. Even so, several key dates remain before that potential shutdown.
November 2: Qualifying Offers and the Start of Free Agency
Five days after the World Series ends, clubs must decide whether to extend qualifying offers to their eligible free agents. For the 2026-27 offseason, the value of a qualifying offer is set at $23.15 million. Players then have until November 17—15 days—to accept or reject the offer. To be eligible, a player must not have been traded or signed after Opening Day, and any player who has received a qualifying offer in the past is ineligible for another. With a new CBA expected before the 2028 season, the future of the qualifying offer system remains uncertain, but for now, free agency opens in earnest. Players with six years of service time and no contract can negotiate and sign with any team. A rush of signings is anticipated before December 1 as players seek new homes ahead of a possible lockout.
November 17: Qualifying Offer Decisions
Eight free agents received qualifying offers for 2027. Those who accept will earn $23.15 million next season; those who reject will test the open market. Under the current rules, teams signing a player who rejected a qualifying offer forfeit a draft pick. Revenue-sharing clubs surrender their third-highest selection, while others lose their second-highest—typically a second-rounder. The team losing the free agent receives compensation picks based on market size and contract value. Six of the eight players who received offers are from revenue-sharing clubs. Barring Seiya Suzuki and David Bednar, a slew of compensation picks could appear at the end of the first round. The Yankees would receive only a fourth-rounder, while the Cubs would get a pick at the end of Competitive Balance Round B. The other six free agents could net their former clubs a first-round pick if they sign for $50 million or more. All of this presumes the qualifying offer system remains unchanged in the next CBA, though current free agents might be grandfathered under the old rules.
November 18: 40-Man Roster Decisions
Perhaps the most consequential deadline of the offseason, November 18 is when teams must set their 40-man rosters. This often forces difficult choices as organizations weigh the risks of protecting or exposing prospects to the Rule 5 Draft. Players who signed at 16 out of high school or internationally have five seasons to be added to the 40-man roster; college draftees have four. Those not protected by this date become eligible for the Rule 5 Draft at December's Winter Meetings. This year, a prolonged lockout could cancel the Rule 5 Draft entirely, granting a one-year reprieve for bubble prospects. Teams' decisions could reveal their expectations about a lockout and their willingness to protect marginal players.
November 20: Non-Tender Deadline
Teams must decide whether to tender contracts to players still under team control but not yet signed for 2027. Most decisions center on arbitration-eligible players, whose salaries can reach into the millions. Players with at least three years of service time, or the top 20 percent of those with two years (Super Two), qualify for arbitration. This deadline is not for exchanging salary figures—that comes later—but for determining whether a player is worth keeping. Those tendered will negotiate a 2027 salary or go to trial. Sometimes, players designated for assignment two days earlier become non-tenders, as the DFA process can take up to five days and a non-tendered player can skip waivers and become a free agent immediately.
December 1: CBA Expiration
The most critical date of the offseason is December 1, when the CBA expires. Owners are expected to lock out the players if no new agreement is reached. Given the current stalemate, a deal by then seems unlikely. A lockout would prohibit communication between players and teams, barring players from working out at team facilities and freezing transactions. It is unclear whether the freeze would extend beyond 40-man roster players, but minor leaguers are now part of the MLB Players Association. Until an agreement is reached, the offseason would be paused. However, neither side is likely to budge until the threat of missed games becomes real. Once the lockout ends, the remainder of the offseason can proceed.
Michael McDermott has covered MLB since 2016, with previous stops at On SI, AZ Snake Pit, Burn City Sports, and FanSided. Follow him at michaelmcd8393.