1) Not making more bigger offseason signings
The Cubs have had one of the bigger payrolls in the sport in recent years and, as such, they were one of the best teams in baseball by making the playoffs five times in six years from 2015 through 2020, including winning the World Series in 2016.
In 2019, they had a payroll of nearly $215 million. In 2022, it was less than $150 million.
It’s not a secret: To get to the playoffs, nearly all of the teams are at the top of the payroll in the sport. You spend money to make money.
This past offseason, the Cubs could have gotten a first baseman, a DH, another outfielder, and more pitching. They would have a had higher payroll and would have been a better team.
Sure, they could have had some injuries (like they did in 2022) but their chance of getting into the postseason would be much better if they addressed their biggest issues and being closer to the $215 million, and not cut the payroll by 31 percent.