
The Milwaukee Brewers dispatched the Tampa Bay Rays on Wednesday night, their 4-1 victory in Game 5 of the World Series giving them their first title in franchise history. Up there in baseball Valhalla, Bob Uecker had the night of his afterlife.
That puts a wrap on the 2026 Major League Baseball season as a whole, meaning the Cincinnati Reds can once again peel themselves off the couch and begin preparations for a 2027 season that, mercifully, cannot possibly be as disappointing as the one that just ended. Baseball wastes little time in sprinting into administrative season, and that began this morning at 9 AM ET when players eligible for free agency were allowed to file.
That includes the likes of Tyler Stephenson of Brock Burke, two names in particular who need a spotlight right here. Though both could have filed for free agency as early as this morning, there’s a five-day window where their former team will be the lone club that can negotiate with them, and since both sure do look like players the Reds would like to have back in 2027 (and beyond), that means the two sides have five days to figure out what a contract would need to look like going forward for that to work. I don’t expect either to sign during this window, but at least there’s a little bit of a heads-up that the Reds will get prior to both getting the opportunity to talk to all 30 clubs beginning next week.
The end of that five-day window will also be the final chance for teams to issue a Qualifying Offer to any of their free agents who were not acquired mid-season. At one point in time that seemed like a discussion the Reds front office was having surrounding Brady Singer, though that has (thank the lord) gone silent amid his season-ending slump. That also marks the day where option decisions must be made, so by then we’ll know if Emilio Pagan has opted into his $10 million salary to remain with the Reds in 2027 or decided to test the free agent waters again. We’ll also have a resolution on the mutual option between the Reds and Eugenio Suarez, though those almost never get picked up by both sides anyway. It’s also the deadline to put players back on the roster from the 60-day IL, so there could be some DFA shuffling (or minor trades) to accommodate the likes of Hunter Greene and Spencer Steer needing 40-man spots once again.
November 1st will see the Gold Glove Awards given out to star defenders across the league. The Reds have no star defenders in the eyes of the powers that be, though – at least, not this year.
November 2nd will see Silver Slugger Award finalists announced, and here’s where we may see the sport’s spotlight swing back to Elly De La Cruz. The 2nd will also see the finalists for all the major BBWAA awards announced, of which Sal Stewart will surely be included in NL Rookie of the Year voting.
November 9th will be the day the Reds find out if Sal won the NL RoY, or not. While the honor itself is a glorious one, keep in mind that the Reds would be in line to get an extra draft pick at the end of the 1st round in 2027 if Sal takes home the prize – and the draft bonus pool boost that goes along with that.
November 9-12 will feature the GM meetings in Las Vegas, ones that will surely be interesting this season given the looming lockout that will be just three weeks later.
November 11th will be the day both the NL and AL Cy Young Award winners will be announced. Chase Burns won’t win the NL award this season despite being firmly in the mix for most of the year, but he’s going to end up with some down-ballot votes.
November 12th is the day the MVPs are announced in both leagues. Elly’s not going to win in the NL this year, but there’s a realistic chance he finishes within the Top 3.
November 16th is the date we’ll see who the BBWAA has included on their ballot for induction in the Hall of Fame, at which point in time social media will become a giant argument over who is worthy of a plaque in the hallway of an old building in an obscure and hard to reach town in upstate New York.
November 17th is the day Silver Slugger Awards are actually announced. It’s also the deadline day for players to accept QOs, if they’d received them. It is also-also the day teams must add players to the 40-man roster to protect them from potential selection in the Rule 5 Draft, which is typically held during the Winter Meetings in December…
…however, the Winter Meetings are currently scheduled for December 7-9th, and that’s after the current Collective Bargaining Agreement is set to expire on December 1st, and there’s zero indication whatsoever that the MLBPA and MLB itself will come to an agreement before that date to postpone an inevitable lockout.
There’s a lot that typically goes on between December 1st and the start of spring training in mid-February, but the dates when those events will occur (or be cancelled) are pretty meaningless at this juncture. Baseball will have to see the arbitration process dealt with in short order at some point, the Draft Lottery to determine the order for next June’s draft will need to take place, and who signs who will all have to fight what figures to be a long, dark transaction freeze until the two sides can figure out how to properly distribute their billions of dollars. It remains to be seen whether teams will make moves in a fury before the expiration date of the current CBA, or if they’ll roll the dice on getting lucky with what’s left after the fact.












