Cubs Should Jump at Opportunity to Sign Ian Happ to Team-Friendly Deal

On May 13, 2017, the Chicago Cubs played the St. Louis Cardinals at Busch Stadium in St. Louis. I was a 20-year-old kid working to become a sports journalist. I was writing for a Sports Blog at the time, and when I found out Ian Happ was making his major league debut, I wanted to capture the moment he got his first hit.

My dad and I were sitting in the 300-level behind home plate, and after his first few at-bats, Ian Happ had yet to record a hit. My friend Charlie was at St. Louis University at the time and was at the game. I wanted to visit him in between innings, and I got my chance.

Unfortunately, when I was waiting for him, Ian Happ hit his first career home run. My dad got it on tape, and I missed a wonderful opportunity. He still brings it up to this day. Well, I missed Ian Happ’s home run; he missed Bobby Hull’s 500th goal in 1970. Joke's on him, right?

Fast forward nine years, and Ian Happ is still stationed in left field for the Cubs. But that time could be coming to an end. The veteran will finally hit free agency in the coming month, putting the future of the longest-tenured Cub in question.

Happ's strong ties to Chicago are undeniable, however. He was even on the organization's official 150th team earlier this season. When the connection is that deep, it can be difficult to say goodbye. Perhaps that's why a recent report from Pat Ragazzo of FanSided says Ian Happ could be willing to take a team-friendly discount to stay in Chicago. Happ is in the final year of his contract, and many are wondering what the best option is for the Cubs.

There is no denying that Happ struggled to produce this season. He’s had some hit-or-miss moments and has trouble hitting from the right side of the plate. For his career, as a switch-hitter, he has hit .248 against right-handed pitchers and .231 against left-handed pitchers. There are flaws to his game. He was not as productive this year as he normally has been.

Yet, the Cubs need to do whatever it takes to re-sign Ian Happ to a team-friendly deal.

A source familiar with Ian Happ's thinking believes he could take a hometown discount in free agency to remain with the Cubs

For FanSided:https://t.co/tgf5PrpTvW
— Pat Ragazzo (@ragazzoreport) September 29, 2026

The Cubs Should Keep Ian Happ in the Mix

Sep 19, 2026; Cincinnati, Ohio, USA; Chicago Cubs outfielder Ian Happ (8) high fives teammates after the victory over the Cincinnati Reds at Great American Ball Park. Mandatory Credit: Katie Stratman-Imagn Images | IMAGN IMAGES via Reuters Connect

With the off-season looming, the Chicago Cubs have too many holes to fill on this roster. The pitching staff requires a massive upgrade in both starters and the bullpen. It has been the Achilles' heel of this team and could cost the Cubs a deep playoff run.

Also, too many Cubs players are set to become free agents, including right fielder Seiya Suzuki. He has already been linked to the Toronto Blue Jays. So, if the Cubs can not re-sign Ian Happ, they might have to fill two corner outfield spots.

The Cubs do have two prospects who could eventually fill those spots: Josiah Hartshorn and former first-round pick Ethan Conrad. However, it's unclear if either is ready to contribute to the major league club anytime soon. Even if Hartshorn does continue his epic ascent up the system, it couldn't hurt to have a stable veteran like Happ fill left field in the meantime.

Indeed, the best option for the Cubs might very well be to re-sign Ian Happ, especially if it comes at a team-friendly rate. It would give the Cubs the flexibility to focus on other areas of the team, and it also keeps their defensive identity intact. Let's not forget that Happ has won four consecutive Gold Glove Awards. Losing a defensive player of that caliber is always a huge loss. With that in mind, it really could be a win-win if the Cubs can get Happ back at a lower price.

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