The Los Angeles Dodgers have defeated the Toronto Blue Jays in a thrilling seven-game World Series, becoming the first back-to-back champions since the New York Yankees won three in a row from 1998 to 2000.

Now that the Fall Classic is over, the MLB offseason begins — and this will be a crucial winter for the Chicago Cubs, as they hope to return to the postseason in 2026.

Here’s a primer for the offseason, what comes next and more to prepare you for the next few months.

It’s everything Cubs fans need to know:

40-man roster

The Cubs have 27 players with guaranteed contracts or under club control on their 40-man roster. Of course, some of these players could be non-tendered (more on that in a bit) or moved:

Pitchers

RHP Javier Assad
LHP Matthew Boyd
RHP Ben Brown
RHP Porter Hodge
RHP Gavin Hollowell
RHP Cade Horton
LHP Luke Little
RHP Eli Morgan
RHP Jack Neely
RHP Daniel Palencia
RHP Ethan Roberts
LHP Justin Steele
RHP Jameson Taillon
LHP Jordan Wicks

Position players

OF Kevin Alcántara
C Miguel Amaya
C Moisés Ballesteros
1B Michael Busch
OF Owen Caissie
OF Pete Crow-Armstrong
OF Ian Happ
2B Nico Hoerner
C Carson Kelly
C Reese McGuire
3B Matt Shaw
OF Seiya Suzuki
SS Dansby Swanson

[MORE: Was the 2025 season a success for Cubs?]

Contract options

The Cubs front office’s first order of business lies in their contract options. The team has five days to exercise or reject contract options for these players:

Shota Imanaga: 3 years, $57 million club option

This is the most complex. The Cubs can pick up the next three years of Imanaga’s contract, which come with a no-trade clause. If the Cubs decline it, then the option becomes a one-year, $15 million player option. If Imanaga declines that, the team can make him a qualifying offer. More on that in a bit.

Got all that? Here’s more on the Imanaga situation.

Andrew Kittredge: 1 year, $9 million club option

The right-hander, acquired from the Baltimore Orioles at the MLB trade deadline, posted a 3.32 ERA in 23 appearances with the Cubs, recorded five saves and had 32 strikeouts in 21.2 innings. He recorded a save in the Cubs’ deciding Game 3 win of the NL Wild Card Series against the San Diego Padres, and had a 5.40 ERA in five playoff innings.

Colin Rea: 1 year, $6 million club option

The 35-year-old was the unsung hero of the Cubs’ pitching staff in 2025. Signed last offseason as rotation depth, the right-hander was thrust into the rotation in April, and made 27 starts and posted a 3.95 ERA in 159.1 innings.

Justin Turner: 1 year, $10 million mutual option

The Cubs signed the veteran in spring training to serve as a bench option. He appeared in 80 games, primarily as a platoon option to Michael Busch, and finished with a .602 OPS, three home runs and 18 RBI. He hit .276 with a .759 OPS against left-handed pitching.

Free agents

RHP Ryan Brasier
INF/OF Willi Castro
RHP Aaron Civale
RHP Brad Keller
LHP Drew Pomeranz
INF Carlos Santana
RHP Michael Soroka
LHP Caleb Thielbar
OF Kyle Tucker

All nine players currently are free agents but are allowed to only negotiate with the Cubs for the first five days of the offseason. After the five days, those players are free to negotiate with any of the other 29 teams.

[MORE: Why Kyle Schwarber, Cubs could reunite as slugger hits MLB free agency]

Qualifying offers

The Cubs can extend a qualifying offer (QO) to free agents, which would tie the player to a one-year, $22.025 million contract. The team has five days to extend the offer, and the players have until Nov. 18 to accept.

The most likely players to receive the QO are Tucker and potentially Imanaga, depending on what happens with his unique option situation.

If the Cubs offer the QO to Tucker and Imanaga, and they decline it and sign elsewhere in free agency, then the team would receive draft pick compensation in 2026.

Either player is very unlikely to accept the QO. Just 14 of the 144 players who have received it have accepted it, the most recent being right-hander Nick Martinez with the Cincinnati Reds last year.

Arbitration

The Cubs have five players eligible for arbitration this winter: left-hander Justin Steele, catchers Miguel Amaya and Reese McGuire, and right-handers Javier Assad and Eli Morgan. They have until mid-January to negotiate a contract for 2026. If not, then both sides submit a salary figure for an arbitration hearing in February.

Since 1980, the Cubs have reached the hearing stage just eight times, with Ian Happ in 2021 the most recent case.

Tender deadline

Nov. 21: That’s the final day the Cubs can offer a contract to a 40-man roster player who is not yet eligible for free agency — the five arbitration-eligible players and the other 15 players with less than three years of service time.

Rule 5 draft

The annual Rule 5 Draft is scheduled for Dec. 10 at the MLB Winter Meetings in Orlando, Fla.

The Cubs will have to add prospects to their 40-man roster by a date in mid-November to protect them from that draft. Here are some notable prospects who will be Rule 5-eligible this winter:

RHP Brandon Birdsell
INF Cristian Hernández
LHP Riley Martin
INF B.J. Murray Jr.
INF James Triantos

Winter meetings

The annual meetings take place from Dec. 8 to Dec. 11. It’s usually a time where deals pick up – Juan Soto signed his mega-deal with the New York Mets at last year’s meetings. The first reports of Tucker trade talks between the Cubs and the Houston Astros emerged during this event last winter, too.

Cubs Convention

The Cubs will host their annual fan fest from Jan. 16 to Jan. 18 at the Sheraton Grand Hotel.

Spring training

Pitchers and catchers will report to Arizona in mid-February. The report date might be early (like it was in 2025, because of the Tokyo Series) because of the World Baseball Classic, which will take place from March 5 to March 17.

The Cactus League opening game date has not been announced.

Opening Day

The Cubs will open their regular-season schedule on March 26 against the Washington Nationals at Wrigley Field.