This story was excerpted from Jordan Bastian’s Cubs Beat newsletter. To read the full newsletter, click here. And_ subscribe to get it regularly in your inbox.

CHICAGO – With another strong showing this season, Cubs outfielder Ian Happ knew what could follow next winter. Given some of the high-profile extensions handed out recently around baseball, Happ was poised to enter the free-agent market as one of the best available bats. 

Barring a surprise deal with the Angels, two-way superstar Shohei Ohtani will be in his own free-agent stratosphere next offseason. The 2023-24 free-agent class will include plenty of pitchers, but the position-player landscape looks to have Matt Chapman and Teoscar Hernández atop the list of options. Happ could have been looking at a big payday. 

“I really, really wanted to continue to wear this uniform,” Happ said. 

Happ reiterated that stance during a press conference on Wednesday, when the Cubs announced a three-year, $61 million extension with the All-Star and Gold Glove Award winner. The deal covers the 2024-26 seasons and is probably fewer years that Happ could have sought as one of the top all-around free-agents on the board. 

Some players are eager to see what free agency brings – former Cubs catcher Willson Contreras called it a “dream come true” to test the waters last winter. A first-round pick by the Cubs in the 2015 Draft, Happ wanted to do what he could to find common ground in negotiations to extend his stay with the only team he has known. 

The two sides negotiated in January while working through his $10.85 million deal to avoid arbitration in 2023. They continued to talk about a deal through Spring Training, but could not meet the soft Opening Day deadline. Happ remained amenable to chatting in-season, and the conversation gained momentum in the last few days. 

“He took a shorter deal than he may have been able to command on the free-agent market,” Cubs president of baseball operations Jed Hoyer said. “But he really wanted to be a Cub and I might admire him for that. He obviously he did really well on this deal. But I also think that he was willing to sort of make a life choice, like, ‘This is the place I'm comfortable.’” 

The Cubs and Hoyer found a structure that grouped Happ in with Dansby Swanson, Nico Hoerner, Seiya Suzuki and Jameson Taillon as players locked in through at least the 2026 season. After the past two years of an aggressive rebuild, Happ said he was excited about trying “to build something and work toward a championship” with the group in place. 

If that meant accepting a shorter deal, so be it. 

“That's the part of an extension, right? There is compromise,” Happ said. “It’s compromising on terms and taking something that is three years and runs through baseball prime, and having to go back out to the market at 32. But, that was my concession to be here.” 

Manager David Ross said Happ’s “belief in this group” really stood out to him. Hoyer was also grateful for the outfielder’s willingness to stay on the North Side, as opposed to taking the potential free-agent money and running to a new town. 

“We don't get this across the finish line if he doesn't want to be a Cub that badly,” Hoyer said. “And that means a lot.”