MLB Insider: Inside the Cubs’ surprising extension with Ian Happ

On Wednesday, the Chicago Cubs extended outfielder Ian Happ. Here’s what the deal means for Happ, the Cubs, and 2023-2024 free agency.

Early in spring training, outfielder Ian Happ sounded ready to test free agency after the 2023 season. Happ and the Chicago Cubs had discussions about a long-term extension, but were unable to find middle ground, and both sides appeared content to enter Opening Day without an agreement in place.

But Happ wanted to stay in Chicago. And the Cubs didn’t want to risk losing Happ in free agency. So the two sides kept in contact and ultimately agreed to a three-year, $61 million contract extension, sources told FanSided. The deal is on top of his $10.85 million salary for the 2023 season.

The $20.33 million average annual value is higher than some industry people expected, but it makes sense for the Cubs. The 2023-2024 free-agent hitting market is the worst it has been in years and Happ would have been among the top options available. As a switch hitter and strong defender, it’s entirely possible that another team could have signed him to a long-term contract in excess of $100 million.

Cubs: Inside Chicago’s surprising extension with Ian Happ

It marks the second homegrown player that the Cubs have extended in 2023, with infielder Nico Hoerner being the first. Under president of baseball operations Jed Hoyer, the team has struggled to keep in-house talent long-term, and ensures that the organization’s core will be built around Happ, Hoerner and star shortstop Dansby Swanson.

In 2022, Happ posted the best season of his career. The 28-year-old hit .271/.342/.440 with 17 home runs and 72 RBI. His strikeout rate dropped. He won his first Gold Glove as he focused solely on playing left field. He hit a career-high 42 doubles and played in a 158 games, also a career high.

The Cubs think that Happ is capable of more and on Wednesday, ensured that he will be staying in Chicago for the next three seasons. Happ passed on a chance to secure a $100+ million contract — and it also weakened what was already a thin crop of hitters in the 2023-2024 free-agent class.