5 MLB playoff stars the Cubs must target this offseason to finally end their October misery

The Chicago Cubs were once again left without an invite to the dance, as the Los Angeles Dodgers and Milwaukee Brewers will face each other in the NLCS. A reminder that the Cubs will never spend as much money as the Dodgers do, and may never be as good at running baseball operations as the Brewers are.

As the Cubs wait for the the abbreviated offseason to start in earnest after the World Series, perhaps they paying closer attention to the players still involved in the playoffs. The idea being that there could be a player, or two, from a playoff team that will be a target for Jed Hoyer and company this offseason.

Here's a player from each remaining team the Cubs should target this offseason

Now, to be clear, this is simply looking at players who should reasonably be available this offseason. In other words, we can't list Shohei Ohtani. Whether through free agency or the the trade market, there should be a chance for the Cubs to get said player on their roster.

Tarik Skubal, Los Angeles Dodgers

Tarik Skubal is the obvious one. The Cubs not only have a need for pitching this offseason, they have a need for quality pitching. Skubal is going to be the top pitcher available on the free-agent market, and well, would be the best way for the Cubs to check that box.

Of course, the reality is that Skubal is going to command what would be the richest contract in the history of the Cubs organization, and for that reason, it feels like we can already take Chicago out as being a serious bidder. Not to mention, a return to LA feels like a lock for Skubal.

Dustin May, Milwaukee Brewers

There's not going to be many options from the Brewers for the Cubs to consider. For one, if Milwaukee makes a player available in a trade, the Cubs feel like the last team they would consider dealing with.

One name to keep an eye on is Dustin May. The Brewers traded for May at the deadline, and he has a mutual option for the 2027 season. Mutual options almost always are declined, and the 29-year-old should hit the free-agent market this offseason. May shouldn't be at the top of the Cubs' wish list this offseason, but he does have the velocity the rotation lacks. Perhaps, he's fallbacl option for the Cubs in November.

Nick Martinez, Tampa Bay Rays

Thought you were going to see Freddy Peralta here? I'd imagine there will be connections between the Cubs and Peralta this offseason, but I would also suspect that his contract demans surpass the Cubs' comfort level.

Nick Martinez feels like a clear free-agent target for the Cubs. He posted a 3.10 ERA in 31 starts for the Rays in 2026, and has experience in the NL Central. Though, to be clear, he wouldn't exact be a change-of-pace from the pitching moves the Cubs have made in recent years.

Randall Grichuk, Chicago White Sox

In a perfect world, the Cubs would bring back Tyrone Taylor. Taylor was the ideal fourth outfielder for the Cubs, considering his success against left-handed pitching offered him a clear spot in the starting lineup. If Taylor isn't back, the Cubs should take a look at Randall Grichuk. He revived his career with the White Sox this year, and posted a wRC+ of 181 against southpaws.

Steven Kwan, Cleveland Guardians

The Cubs have already been connected to Steven Kwan, and it's still not certain the Guardians will trade him this offseason. If they do, he should be the type of upgrade the Cubs target for their offense, as he offers an ideal mix of a contact-oriented approach on offense, and is a regular Gold Glove candidate in the outfield.

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