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3 essential pieces of the Chicago Cubs future, 2 players on the discard pile

These five players will determine the future of the Chicago Cubs
ByRich Eberwein
Sep 30, 2026; San Diego, California, USA;  Chicago Cubs dugout looks on in the ninth inning against the San Diego Padres during game two of the Wildcard round for the 2026 MLB Playoffs at Petco Park.  Mandatory Credit: Denis Poroy-Imagn Images
Sep 30, 2026; San Diego, California, USA; Chicago Cubs dugout looks on in the ninth inning against the San Diego Padres during game two of the Wildcard round for the 2026 MLB Playoffs at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images | IMAGN IMAGES via Reuters Connect

Now that the Chicago Cubs are officially eliminated from the playoffs, it's time to assess this roster and look at who can be long-term pieces for the team's future. The 2027 team will look very different thanks to 10 players from the current roster becoming unrestricted free agents, and five players with mutual or player options that likely won't be exercised. After an extremely disappointing postseason exit and a lot of holes to fill, this offseason will test the front office's promise to deliver consistent success on the North Side.

As part of those evaluations, it's likely that Jed Hoyer and Co. will identify players essential to the plan moving forward, and those who can be moved on from.

3 essential pieces of the Chicago Cubs future

Pedro Ramirez

Pedro Ramirez made his Major League debut in 2026 and played well enough to avoid getting sent back to the minor leagues. That says a lot about Ramirez's talents and ability to adapt, especially for a player who is only 22 years old. Primarily a second baseman, Ramirez saw time at third base, first base, and in the outfield in his inaugural campaign.

And his ability to play serviceable defense in the outfield will be vital for the Cubs next year with Ian Happ and Seiya Suzuki becoming free agents. It's not a guarantee that both players are done with Chicago, but I don't see the Cubs giving Suzuki a hefty multi-year contract as he goes into his age-33 season, and Happ's production as a hitter is declining. There's a good chance that the Cubs give one of those corner outfield spots to Ramirez and hope that he can continue to handle Major League pitching as an everyday player.

Braxton Garrett

Braxton Garrett was the 2026 trade acquisition that flew under the radar. He only made one start for the major league team and spent the rest of the year with the Triple-A Cubs, where he served as a solid starting pitcher. He made seven starts and posted a 4.11 ERA over 30 2/3 innings pitched, with 32 strikeouts and a .209 opponent batting average.

Again, Matthew Boyd, Kevin Gausman, Shota Imanaga, David Peterson, and Clay Holmes are all free agents. I think Garrett will be a vital piece of the rotation next year who could be one of the few sources of stability. There is so much uncertainty surrounding Justin Steele and Ben Brown's injuries and their long-term status, so trading for Garrett could go down as one of those underappreciated life-savers.

Kevin Alcantara

I am not ready to disregard Kevin Alcantara. I think he has a lot of things to work on as a hitter, but I like the idea of him getting regular playing time in the majors. I don't think he's a guy who can succeed as a bench guy or pinch runner. His value will come as an everyday player, and the Cubs can finally give him that runway in 2027.

I think he will surprise us if given the opportunity and provide this team with some much-needed power, flair, and youth to pair with Pete Crow-Armstrong in the outfield. This path makes the most sense from a financial standpoint too, because there aren't many attractive outfielders on the market to target aside from Suzuki and Randy Arozarena. Both of those guys are over 30-years-old and likely out of the Cubs' comfort zone in terms of price, so going young with Alcantara makes more sense.

If it doesn't work out, this move can at least buy time while prospects like Josiah Hartshorn and Kane Kepley develop and work closer to their major league debut.

2 Cubs players on the discard pile this offseason

Edward Cabrera

Edward Cabrera's first season in Chicago was nothing short of a disaster. I liked the trade when it happened, because Cabrera had a lot of upside and arguably still does. But multiple injured list stints and poor performance as both a starter and reliever leave a bad taste in my mouth.

Especially because the Cubs sent their best prospect to the Marlins in outfielder Owen Caissie. A guy that the team would love to have right now to fill Suzuki's spot in right field moving forward. Cabrera still has one year of team control and with five starting pitchers hitting free agency, the Cubs need to figure out how to keep him in the starting rotation or risk this trade looking like one of the worst in recent memory.

Matt Shaw

In a lot of ways, Matt Shaw and Pedro Ramirez fit the same mold. They can both play multiple positions, are great baserunners and hit for contact more than power. It makes sense to keep one and trade the other given the team's pitching needs.

Shaw has just enough upside to be a main component of a trade, which would ideally nab the Cubs a controllable starting pitcher or reliable bullpen arm.

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