As the Chicago Cubs window opens, the time to act is now

The Chicago Cubs are now facing a crucial time in the offseason where there are a lot of lines in the water with not a lot of fish to catch. With Shohei Ohtani now off the market and staying in Southern California to join the Dodgers, the floodgates have opened up and teams are going to scramble and pay up to make a contender.

The Cubs saw a remarkable uptick in 2023, finishing above .500 in a full season for the first time since 2018 (the 2020 season was 60 games). Now, Jed Hoyer and the Cubs need to capitalize on their advancement and go for a championship. The heavy hitters (Dodgers, New York Yankees) are going to continue swinging this offseason, so the Cubs are going to need to step in the box and take some hacks as well.

"The Cubs organization is valued at $4.1 billion, according to Forbes, with an ownership group that makes a lot more on top of that by owning a lot of the area around Wrigley Field. They should always be in the top five in payroll, though team owner Tom Ricketts has said he isn’t going to guarantee that."

Sahadev Sharma of The Athletic wrote a wonderful piece on Hoyer’s reluctance to spend despite being a top-market team (Subscription Required). This team cannot improve by standing pat, relying on what’s in-house, or waiting another year. Hoyer has to make a move. Cody Bellinger will either need to be signed or replaced. A long-term option at first base is a big hole to fill. No matter who you are, pitching is always going to be a need – both starting and relieving. There’s a lot to do and not a lot of time to do it, so get on out there.

It does not all have to be in free agency, either. The Cubs farm system is rich with prospects and talent quickly on the rise. As we enter “win now” mode, some of these prospects can be traded to teams like the New York Mets, looking to the future rather than now, for a Pete Alonso rental. Then, hopefully, you could extend him and keep him long-term. This is just one example of a hypothetical trade target.

Whether it be signing Bellinger, signing Rhys Hoskins, or trading for Pete Alonso, this team needs a bat and a glove to complete the field (throw Matt Chapman in that mix too), and potentially multiple. Trade for Glasnow or even Shane Bieber to add to this rotation. David Robertson is a wonderful bullpen arm still available to be signed.

Former Cubs skipper Joe Maddon pointed out this week on 670 the Score that Chicago Cubs fans are the greatest fans in history. It’s a loyal fanbase, it’s a hungry fanbase, and it’s a smart fanbase. It does not take a genius to know the money is available to be a top spender in free agency, like the Dodgers and Yankees. When beers in the stands approach $15 and there are cup snakes as long as the strip of bars on Clark Street, the money is there.

2016 was seven long seasons ago. The groundwork has been laid out and the pieces are surrounding and available. The window is opened and it is up to Hoyer, Tom Ricketts, and the Cubs brass to either keep it open or shut it down.