MLB offseason has key deadlines for Cardinals to make a splash before ominous winter

Congratulations to the Milwaukee Brewers for winning their first ever World Series title but for the other 29 teams, that means the offseason truly begins. While the Brewers are parading through the streets of Wisconsin, front office staff from the rest of the league will be strategizing their offseason plans as they look towards getting their own teams into October contention.

Unlike normal offseasons, this winter comes with plenty of questions that do not have a definite answer and likely will not until the calendar flips to 2027. Even with the impending lockout, teams will have a month to make roster additions or subtractions before the baseball world goes dark for an undetermined amount of time. For the St. Louis Cardinals, they can check off plenty of boxes before December and set their roster up for a solid 2027 season, whatever that will look like.

MLB offseason begins as Cardinals look to return to National League dominance

October 29: Free Agency begins

With the 2026 season officially coming to a close with the Brewers' victory, MLB free agency begins with a caveat. Players eligible for free agency can begin negotiating contracts the day after the season ends, but there is a five-day waiting period before those players can officially sign their new deals.

November 1: Gold Glove award winners announced

Before teams and players officially put pen to paper, MLB will announce one of their biggest awards on the first day of November. In an effort to stay in the news cycle even after the season ends, MLB will announce various awards throughout the winter and the first award winners will be honored with a Gold Glove award.

The Cardinals have three finalists for the prestigious fielding award and have a good shot of having at least one winner. Shortstop Masyn Winn looks to repeat as the best defender at his position and the metrics point to him being a potential favorite for his second Gold Glove. His double play partner, rookie JJ Wetherholt, handled his new position with ease during his debut season, grading out as one of the best second basemen in all of baseball. While he may miss out on the Rookie of the Year award, Wetherholt may be able to add one trophy to his mantle this winter. The third finalist is pitcher Michael McGreevy, who made plenty of plays bouncing off the mound and will have to fend off veteran Chris Sale and standout rookie Nolan McLean.

November 2: Free agents can officially sign contracts

In the second iteration of official free agency, November 2 is the first day that players can sign their new deals. From October 29 through this date, there may be announcements of players agreeing to contracts with teams, but until the signature is dry on November 2, those are considered to be rumors.

November 9: Rookie of the Year award winner announced

In the second award announcement of the offseason, MLB will follow up their Gold Glove winners a week later with the top rookies in each league being honored. JJ Wetherholt looked like a front runner for the NL honor, but a down second half dropped him behind Sal Stewart and Carson Benge in the running. Recently, Stewart was named the Players Choice as the NL's top rookie, so the Cardinals may be leaving November 9 empty handed.

November 10-12: GM Meetings

In the middle of November, front office personnel will get out of the chilly air and meet in Las Vegas for the annual GM Meetings. During this three-day period, GMs and other important staff members will be in constant contact to set prices for trade pieces or begin conversations for later deals. The amount of activity coming out of Vegas will be an interesting story as GMs may be aggressive to get things done before the lockout or sit on their hands until their is more clarity for the 2027 season. For Bloom, there may not be much difference for him this offseason as he appears to have a solid roster ready for the next campaign.

November 17: Qualifying offers declined or accepted and Rule 5 deadline

A few days later, the Cardinals will have a couple decisions to make on their roster. On November 17, players who were given a Qualifying Offer will have the opportunity to accept or decline the one year salary offer. The Cardinals do not have any players that will be receiving a QO, so the other event on this date may be more important.

Also on the 17th, teams must make their final 40-man moves to protect their Rule 5 eligible players. This will be another fun case study because the CBA may impact the Rule 5 draft, allowing teams to either be more aggressive or more passive in their protections.

November 20: Non-tender deadline

Later that week, teams will have to decide the futures of some of their fringe players with the non-tender deadline. On November 20, teams will decide whether they will re-sign their current players for another season based on their rookie contracts or non-tender these players, meaning they will become immediate free agents. The Cardinals have some non-tender candidates like Nolan Gorman and Pedro Pages, but they have not yet tipped their hand for any of their players.

December 1: Expected lockout begins

Finally, on December 1 the current CBA expires and the anticipated lockout will begin. Plenty of experts around the league are pessimistic about an uninterrupted offseason, so the end of the 2026 calendar year may set up a dark and ominous start for 2027.

Add us as a preferred source on Google

Follow