3 trade targets who could help the Cubs avoid another painful postseason disappointment

After an embarrassing sweep in the Wild Card series at the hands of the Padres, the Chicago Cubs enter the offseason facing near-certain upheaval all around their roster. Whether it's dreams of adding Tarik Skubal to the rotation or the frustrating reality of Seiya Suzuki's impending departure, no one should question the fact that there's big change coming to the north side this winter. The only question is: how can Jed Hoyer and his front office make the most of it?

One place they'd do well to look at trying to improve is by bringing in players with postseason pedigree. While Alex Bregman and Dansby Swanson both have World Series rings, the vast majority of this clubhouse has minimal postseason experience and even less hardware to show for it. A few more guys who have done it before certainly wouldn't hurt, and a handful of potential trade candidates could really fill that void for Chicago. Here's a look at some of the options:

Nathan Eovaldi is the exact sort of big game pitcher the Cubs were missing this year

The Cubs tried to add an experienced postseason veteran to their rotation by bringing in Kevin Gausman over the summer, and while that attempt was admirable, it just didn't work out. The best way to fill that void might be trading for Eovaldi, who the Rangers got close enough to dealing this summer that they reportedly discussed his full no-trade clause with him before the deadline.

The 36-year-old hurler has battled injuries all throughout his career, so Cubs fans shouldn't count on him for 30 starts next year. With that said, he's managed to post 275 2/3 innings of 3.04 ERA ball since the start of the 2025 season. That's clear front-of-the-rotation production when healthy, and Eovaldi is also one of the most decorated postseason pitchers active in the majors with two World Series rings and a career 3.05 ERA in 79 2/3 postseason innings.

The Rangers are clearly interested in clearing some significant salary from their books this offseason, and it wouldn't be a shock to see them try and move Eovaldi. If he's put on the market, the Cubs would be smart to pounce on the opportunity to add a high-impact veteran with his playoff resume to their ranks.

Bryce Harper is still looking for his first ring, but his bat could help the Cubs like no other come October

Cubs fans have been dreaming about Harper playing his home games at Wrigley Field for almost a decade now, and with the Phillies at a crossroads that might be more feasible now than it's been in a very long time. Dave Dombrowski and the rest of Philadelphia's front office are approaching the point where they'll have no choice but to consider dealing some of their big contracts to retool a bloated payroll, and rumored tensions between Harper and Dombrowski could further catalyze a deal.

Harper is a slam-dunk future Hall of Famer, but the one thing his resume is missing is a World Series ring. That's not for lack of trying on his part, however, as he's a career .271/.382/.593 hitter in the postseason with 18 homers and 15 in just 60 playoff games. Power is the name of the game in the playoffs, and adding Harper would be a great way to offset the loss of Suzuki and avoid relying too heavily on all-hit, no-power bats like Nico Hoerner and Pedro Ramirez next year.

Of course, Harper being traded anywhere (much less to the Cubs) is something of a longshot. Star players under long-term deals rarely move for a reason, and that goes double for a player with a no-trade clause and a stated desire to finish his career in Philadelphia. If the Phillies consistently failing him in October changes his mind, however, the Cubs would do well to swoop in and make the most of the opportunity.

Teoscar Hernandez could be a more realistically available trade chip with October pedigree

While Harper moving this winter feels somewhat farfetched, the same cannot be said for Dodgers outfielder Teoscar Hernandez. Kyle Tucker isn't going anywhere for better or worse, and with youngsters like Andy Pages and Josue De Paula clearly ready for everyday playing time in the outfield there just doesn't seem to be much room for Hernandez on the Dodgers' roster next year.

That's something no one should be surprised to see the Cubs take advantage of. Hernandez could help bring some of the culture of the back-to-back World Series champs to Chicago, and in doing so also help replace the big right-handed bat of Suzuki headed into next year. Hernandez has been a 110 wRC+ hitter in the regular season this year, a figure that matches his career postseason numbers.

While he's struggled this October (along with much of the Dodgers' offense), Hernandez might be the simplest way to add some World Series experience to this Cubs roster. As Michael Conforto and Cody Bellinger can tell you, it certainly wouldn't be the first time the Cubs plucked a Dodgers outfielder on the downswing from their roster and helped him revitalize his career. It's hardly the most exciting move the Cubs could make, but this deal would be a good start to fixing this offense's holes.

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