The Cubs are headed into an offseason that figures to bring real change, and the cleanest way to start fixing what went wrong is obvious: add players who’ve already been through October and come out the other side with rings.
That matters after a Wild Card sweep at the hands of the Padres left Chicago with another painful ending and a roster in need of a shakeup. There’s talk of major additions, including dreams of Tarik Skubal in the rotation, and there’s also the possibility of Seiya Suzuki moving on. However it unfolds, Jed Hoyer and the front office have a clear lane to improve: target proven postseason performers.
One name that fits the bill is Nathan Eovaldi. The Rangers reportedly discussed his full no-trade clause with him before the deadline this summer, so he was already close enough to the trade block to make this more than a fantasy.
At 36, he’s not the kind of pitcher anyone should expect to make 30 starts, especially with the injury issues that have followed him throughout his career. But when he’s been available since the start of the 2025 season, he’s been excellent, posting 275 2/3 innings of 3.04 ERA ball.
More importantly for Chicago’s purposes, Eovaldi owns two World Series rings and a 3.05 career ERA in 79 2/3 postseason innings. That’s exactly the kind of big-game arm the Cubs tried to chase when they brought in Kevin Gausman over the summer, and it’s the kind of veteran presence that could matter in October.
Bryce Harper is the splashier swing, even if it feels like a long shot. Cubs fans have imagined him in Chicago for nearly a decade, and the situation in Philadelphia could make that conversation at least worth having.
The Phillies are at a crossroads, Dave Dombrowski and the front office may eventually have to consider moving some of their major contracts to rework a bloated payroll, and there have even been rumors of tension between Harper and Dombrowski. Harper still doesn’t have a ring, but his playoff track record is loud: a .271/.382/.593 postseason line, 18 homers and 15 doubles in 60 playoff games.
If the Cubs lose Suzuki, Harper’s power would be a huge answer, especially with less imposing bats like Nico Hoerner and Pedro Ramirez in the mix. The catch, of course, is that this would be a difficult move to pull off.
Harper has a no-trade clause and has said he wants to finish his career in Philadelphia.
Then there’s Teoscar Hernandez, who looks much more available than Harper and may be the most realistic fit of the three. The Dodgers have Kyle Tucker locked in, and with Andy Pages and Josue De Paula seemingly ready for everyday outfield roles, Hernandez could be squeezed out.
That’s where the Cubs could step in. Hernandez would bring some of the feel of a back-to-back World Series team to Chicago, and he’d help cover for the possible departure of Suzuki with another right-handed bat.
He’s been a 110 wRC+ hitter in the regular season this year, and that lines up with his career postseason production as well. He hasn’t had a clean October himself, along with much of the Dodgers’ lineup, but he still offers a straightforward way for the Cubs to add postseason experience.
And if that sounds familiar, it should: the Cubs have done this before with Dodgers outfielders like Michael Conforto and Cody Bellinger. It may not be the flashiest path, but it could be a smart one.
In Other News...
David Ross Is Facing A Tough Test To Get Another Shot
David Ross has spent the past couple of seasons away from the dugout, settling into his role as an MLB analyst for ESPN after being dismissed by the Cubs in 2023. Still, his name is back in circulation as the Mariners look for a new manager following their split with Dan Wilson, and that alone says plenty about how Ross remains viewed around the game despite his time away from coaching.
Rosss four years on the North Side produced a 262-284 regular-season record, along with a division title in 2020, a rsum that gives him both a point of pride and a few questions to answer if he wants another shot. If Seattle does move forward with him among its candidates, the conversation will be less about what he was in Chicago and more about whether he is the right fit to guide a club trying to reset after a managerial change. [Read more 🡒]
Former Cubs Infielders Just Reopened An Old Roster Debate
Miles Mastrobuoni and Vidal Brujan have both hit minor-league free agency, according to the MiLB transactions log, and that alone reopens a familiar Cubs roster debate about depth in the infield. Both players spent time in Chicago as utility options, the sort of move that can look useful in the moment but rarely settles the bigger question of whether the club has enough dependable bench help when the season turns.
Brujan arrived in a December 2024 trade, was designated for assignment in July 2025, and has since moved through the Orioles, Braves and Mets organizations. Mastrobuoni, who debuted with the Rays in 2022 before coming to the Cubs, has seen his offense trend the wrong way, which helps explain why both are likely headed toward minor-league deals this winter rather than clearer paths back onto a big-league roster. [Read more 🡒]
Cubs Offseason Trade Debate Starts With Two Massive Roster Needs
The Cubs offseason to-do list already looks fairly clear, and it starts with two areas that tend to shape everything else: catching and pitching depth. If they want to take a meaningful step forward, they will need to upgrade both the everyday mix and the arms around it, which is why trade speculation is already circling names like Hunter Goodman behind the plate and Shane McClanahan or Mason Miller on the mound.
Chicagos front office has spent enough time around this roster to know the answer probably will not come from one move alone. A catcher who can stabilize the position and a front-line pitcher or impact bullpen arm would each change the equation in different ways, and the Cubs are at the stage where they have to weigh fit, cost and upside all at once. The debate is really about how aggressive they want to be, and which need they decide to attack first. [Read more 🡒]