Building Cubs’ Holiday Wishlist: Starting Pitcher, Bullpen, Outfielder

It’s finally Thanksgiving, which means the holiday season is upon us.  Some people argue that only now can you truly listen to Christmas music, but the correct opinion is that those tunes were viable weeks ago. Make sure to enjoy the food and time with family, and, of course, some football. The Bears game on Friday could put the cherry on top of what should be a great weekend, although it’s their first real test in several months.

People have already started creating their holiday wishlists with Christmas less than a month away. Kids will want the latest gaming consoles, adults may want new clothes, and Cubs fans want their team to spend more money. The front office wants more pitching, among other things. If the team intends to compete again prior to 2032, Jed Hoyer’s offseason wishlist must include a starting pitcher, bullpen arms, and a corner outfielder.

Dylan Cease signed with the Blue Jays on Wednesday, a move that caught a lot of people by surprise. Not because he went to Toronto, but because he got more money than pretty much anyone expected. On top of that, it’s rare to see a player of his stature sign before the Winter Meetings. His decision came a day after Sonny Gray was shipped up to Boston, signaling that the hot stove action may get started earlier than usual this winter.

The Cubs need a good starting pitcher to do more than just provide depth. Whether they end up acquiring an ace or someone for the middle of the rotation, it’s time to pay up for a legitimate arm to help this team make a deep playoff run. They could spend money and go after top free agents like Ranger Suárez and Michael King, or they could opt to trade organizational pieces for arms such as Edward Cabrera or Pablo López.

Phil Maton was the first move of the winter for Hoyer, marking a rather quick start to what is a pivotal offseason. Maton is as consistent as they come, logging 60 or more innings every year since 2021. His strikeout rate will be a huge help to the Cubs’ bullpen. But that alone isn’t nearly enough after they lost several arms to free agency, including Brad Keller, Drew Pomeranz, and Caleb Thielbar.

In addition to Maton, the Cubs still need to add several pieces to retool what was a very effective bullpen this past season. Hoyer and his pitching infrastructure, led by Tommy Hottony and Tyler Zombro, have done a great job at finding projects and turning them into successful relievers, which is likely the route they’ll follow once again this winter.

Losing Kyle Tucker stings, but after his inconsistent stint in Chicago, parting ways may not be the worst option. Nonetheless, replacing his offensive production will require Hoyer to spend some resources in either free agency or on the trade market. Craig Counsell could deploy Seiya Suzuki in right field if the team brings in a designated hitter, or find another way to move around positions.

Old friend Kyle Schwarber needs a home and would be an interesting fit if Tom Ricketts wants to open up his wallet. Alex Bregman, whom the Cubs pursued last offseason, is once again a free agent. Bringing him to Chicago remains a possibility, although Matt Shaw makes that situation tricky (but not impossible). Rob Refsnyder would cost much less than those others, but he’s an almost perfect fit on paper as a fourth outfielder.

There are many, many other options not mentioned above that the team will consider over the next three months. The Cubs have both the money and prospects to acquire elite talent, but it’s their willingness — or lack thereof — to do so that will make things both frustrating and interesting to watch unfold.

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