The Cubs' recent playoff success sets the stage for crucial offseason decisions. Will the front office invest heavily to build a championship contender?
This is shaping up to be one of the most important offseasons for the Cubs in recent years. That’s because the North Siders are finally in a spot where they can compete for a World Series title next season.
They just made the postseason for the first time since the shortened 2020 campaign and won a playoff series for the first time since the 2017 season. Those are significant milestones for a franchise that missed the playoffs in four straight years prior to 2025.
This postseason run could be compared to the 2015 team that made the playoffs, advanced past the first round, and looked to be taking a step forward. However, that team wasn’t quite ready for the big stage yet.
Then the following year, the Cubs ran it back with a large majority of their players and wound up winning the World Series for the first time in 108 years.
If the current Cubs team wants to be like that 2016 World Series team, the front office has to make moves this offseason to get them over the top. That starts with adding players via free agency and making trades.
As it stands now, the Cubs have $166 million on their payroll for the 2026 season. That number could be different by next week, depending on whether Chicago declines Shota Imanaga’s three-year, $57 million club option, Andrew Kittredge’s one-year, $9 million club option, and Colin Rea’s one-year, $6 million club option.
Even if the Cubs bring back all three players, and we include the arbitration and pre-arbitration totals, Chicago's payroll could be roughly around $186 million before the offseason begins. That still gives the front office plenty of room to add impactful players.
However, the front office must have a payroll larger than $211 million, which was the team’s payroll for the 2025 season. The Cubs have to get as close as possible to that first luxury tax threshold because it’s highly unlikely that Tom Ricketts will pay the luxury tax.
With the luxury tax set at $244 million for the 2026 season, that would give the Cubs $58 million to spend this winter. That number could be even more if players like Justin Turner (mutual option) and Imanaga don’t return.
It’ll be interesting to see how much the Cubs are willing to spend in free agency. This team made significant strides in 2025, and it would be disappointing to see the front office not make big moves this winter.