Cubs’ Ian Happ Partnership Reaches Brink

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CHICAGO, ILLINOIS - SEPTEMBER 14: Ian Happ #8 of the Chicago Cubs at bat against the Atlanta Braves at Wrigley Field on September 14, 2026 in Chicago, Illinois. (Photo by Michael Reaves/Getty Images)

The Chicago Cubs‘ season is on the line.

They lost Game 1 of the best-of-three NL Wild Card Series at the San Diego Padres on Tuesday night, and in convincing 8-0 fashion. The Cubbies have no choice but to win on Wednesday, because if they lose, their season would be over.

It would also mark a crucial pivot point in the future of multiple important Cubs players.

The likes of Kevin Gausman, Seiya Suzuki and Ian Happ can all be free agents after this season. So when the season ends, their futures officially come into focus.

Happ, in a lot of ways, is the most fascinating — because he’s the longest-tenured player among pending Cubs free agents. He’s been in Chicago for a long time. It’d be odd to see him in any other uniforms.

But whenever the Cubs’ season ends, whether on Wednesday or later on, he and the Cubs will have some decisions to make.

Is Ian Happ Leaving Cubs?

Nothing has been decided about Happ’s future yet, at least not publicly. All we can do is read the tea leaves.

Happ had an emotional quote before the final home regular season game at Wrigley Field, and that’s what started speculation that he could end up going elsewhere in the offseason.

“This is the last controllable day here,” Happ said last week, via ESPN’s Jesse Rogers. “I’ll take it in. It’s crazy. 10 years of memories. There will be emotions. I want to savor it. There’s no fanbase more supportive of its players.”

Happ was also right to recognize that day in Wrigley Field, because the Cubs won’t be back there unless they rally and advance to the Divisional Round. The entire Wild Card Series gets played at the better seed, which in this case is the Padres.

Happ’s departure (or not) probably won’t depend on what happens the rest of the playoffs, unless he plays a supremely heroic role in a surprise deep run. For now, Happ and the Cubs would simply like to keep their season alive.

Ian Happ Cubs Career

Happ has been with the Cups since he first became a professional baseball player.

He wasn’t selected by anyone in his high school senior year of the draft out of Mount Lebanon High School in Pittsburgh, so he headed to the University of Cincinnati to play college baseball at the Division I level.

That worked out, and Happ was chosen No. 9 overall by the Cubs in the 2015 MLB Draft.

He made it to the major leagues with the Cubs in 2017 and immediately hit 24 home runs to quickly live up to the hype surrounding him.

Happ is both a talented switch-hitter and a great fielder with a strong arm in the outfield.

Happ’s best season by Wins Above Replacement (4.3) was 2022, his lone appearance in the All-Star Game. He hit 42 doubles and 17 home runs that season while hitting a career-best .271.

He has won four Gold Gloves as an outfielder, too.

Happ is wrapping up a contract that paid him $61 million across the last three seasons.

Can he get $20 million per year from the Cubs, or from anyone else, in free agency? That’s a question that it will take time to answer.

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Cubs’ Ian Happ Partnership Reaches Brink

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