Chicago Cubs: What to do with free agency-bound Ian Happ?
The Chicago Cubs may be working towards a playoff berth, but they also have to be looking at the situation facing them after this season.
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A good portion of the current roster will be eligible for free agency and many big decisions will have to be made when it comes to roster and budget for 2027 and beyond.
Among those potentially leaving are core veterans Ian Happ, Seiya Suzuki, Matthew Boyd, Shota Imanaga, and Carson Kelly. Then, there are the short-timers and add-ons who will also potentially be leaving like Kevin Gausman, David Peterson, Michael Conforto, Hoby Milner, Tyrone Taylor, Aaron Civale, Trent Thornton, Ryan Rolison, and likely Clay Holmes, who’s sitting on a $12 million player’s option for 2027.
While the Cubs could go out and fill all those spots with new acquisitions, they’d probably prefer to keep a few around—especially the core veterans.
Left fielder Ian Happ is one of those who should be considered in the “must retain” conversation.
There’s definitely a case to be made against keeping the 10-year veteran around.
The argument against Ian Happ

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His long stretches of flat-lining offensive production are beyond frustrating and, ultimately, problematic for a Cubs team in “win now” mode. Currently hitting .215, he’s on track to have the lowest average of his career in this contract year.
The biggest case against re-signing Happ, though, may be that spending money to do so could cost the team money arguably better spent on keeping Seiya Suzuki or on pitching over the offseason.
The 32-year-old is currently finishing up a 3-year, $61 contract extension and will surely be expecting more money for a longer time in any new deal. Even given his defensive excellence and his leadership role on the team, spending $100+ million for five more years of Happ doesn’t seem like outfielder money optimally spent—especially with a trio of quality outfield prospects (Josiah Hartshorn, Ethan Conrad, and Kane Kepley) a couple of years away from being major league-ready and Suzuki also heading into free agency.
Jordan Campbell of Cubbies Crib succinctly sums up the dilemma facing the Cubs:
“A quick reminder on the truths facing the Cubs this season. Both Happ and Suzuki will be free agent this offseason. Most of the Cubs’ pitching staff will also hit free agency. The Cubs’ primary focus will be on adding pitching. Suzuki is pacing to be one of the best free-agent bats available. Happ should also be coveted, but his peculiar 2026 season likely places him in tier below Suzuki’s contract projections.”
But Happ’s plug-and-play consistency…

Having Happ around in left field, on a team with explosive offensive potential all around him, would be nice. He’s a low-volatility plug-and-play asset who’s a known, consistent commodity. You know you’re getting a Gold Glove left fielder, 20+ home runs, a league-average (or slightly lower) batting average, and pockets of high-end production around his extended slumps.
He’s also a player firmly invested in the city of Chicago with his roots firmly planted there.
Given his affinity for the city and for the Cubs organization, could Happ be willing to go for a two or three-year extension with just a slight raise in AAV—maybe even a good chunk of the money coming via deferred payment?
That might be the compromise to make. Because, realistically, if the choice ends up being either him or Suzuki, there’s probably more of a case to be made in retaining the Japanese star.
The post Chicago Cubs: What to do with free agency-bound Ian Happ? appeared first on ChiCitySports.
Source: https://www.chicitysports.com/chicago-cubs-ian-happ-free-agency-seiya-suzuki/
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