Sunday, September 24 2023

Ian Happ just missed out on being a part of the last great Cubs team. Rather than test the open market this winter as one of the best position players available, Happ has secured an opportunity to be an important part of the next great Cubs team. 

On Wednesday, Chicago announced a three-year extension for Happ that will reportedly pay him $61 million guaranteed. (That’s on top of the $10.85 million he’s making in 2023 in his final year of arbitration.) A dearth of high-profile hitters in next winter’s free-agent class suggested that Happ could be in line for a sizable payday on the open market after this season, either in Chicago or elsewhere. Instead, Happ, who has consistently communicated a desire to remain a Cub, opted to extend his stay on the North Side through the 2026 season.

Drafted ninth overall by the Cubs in 2015, Happ made his MLB debut on May 13, 2017, roughly a month after his new teammates received their 2016 World Series rings to commemorate one of the most iconic championships in baseball history. Over the ensuing six years, the core of the World Series team gradually departed via trade and free agency. Once an exciting young talent hoping to bolster the star-studded roster with consistent championship aspirations, Happ was suddenly a veteran in his own right and now stands as the second-longest tenured Cub behind ace Kyle Hendricks.

“When we moved on from all those guys, that was the time that it was like, ‘Oh, I get to park in the front row now,” Happ told FOX Sports during spring training. “Those are the little things that you’re like, wow, that’s changed.” 

Happ cited how quickly he found himself in the shoes of the veterans he once looked up to. The seventh-year outfielder — along with 25-year-old second baseman Nico Hoerner, whom the Cubs also recently extended — has become the standard to emulate for the exciting group of prospects in the club’s pipeline. 

“I was thinking about [Cubs outfield prospect] Brennen Davis. When I got to the big leagues, I was 22 and [Anthony] Rizzo was 27. Now I’m 28 and [Davis] is 23.”  

At the 2022 trade deadline last July, it seemed like Happ — who had just made his first career All-Star Game — could be the next to go. With so many veterans having already been flipped for prospects and another losing season in progress, his name was consistently thrown around in trade discussions alongside catcher Willson Contreras. While Contreras ultimately left for St. Louis in free agency, Happ remained in tow for the final year of his contract despite his future in Chicago being cloudy. This extension clarifies both the Cubs’ and Happ’s intentions to continue building together. 


Though the timing of the extension may seem unusual for a player so close to free agency, it tracks with Happ’s deep appreciation for playing for such a historic franchise. Baseball may be a business for teams and players alike, but getting to call Wrigley Field home is a unique privilege that Happ has never taken lightly.  

“I was a baseball fan my whole life,” Happ said. “I watched games on WGN when I came home from school. I never even could grasp what Wrigley Field was until you’re really there and you step on the field.”

More specifically, Happ is especially grateful he reached the big leagues before the dugouts in Wrigley underwent significant renovations. 

“I got really lucky because in ’17, we had the old dugout. I wish the people that came up now got to see that. We had this tiny dugout that had a urinal that we called Ernie Banks Toilet,” Happ fondly recalled. “It was so old … it was like, Ernie used that!” 

The dugouts were one of the last vestiges of an iconic ballpark that has slowly been remodeled from the inside out over the past decade. 

“We had the nice clubhouse and we had all that stuff but there was still this feeling like, ‘Wow, this is so historic.’ And you still get the feeling when you get out on the field, that Babe Ruth called his shot there and that [Ryne] Sandberg and Ernie Banks and Ron Santo and those guys played on that field. You still get that connection. But to feel like you sat in the exact same seat in the dugout as one of those guys … that was such a connection that I was so lucky to get in ‘17.”

This commitment to the Cubs is about much more than sentimentality, of course. It’s about winning. Outside of two quiet losses to the Marlins in an empty Wrigley Field during the bizarro 2020 playoffs, the Cubs have not appeared in the postseason since Happ’s sophomore season in 2018. Reflecting back on the success he witnessed in his early years in the organization, Happ is adamant that it was about the year before the championship year that really set the tone for what turned out to be a legendary group. 

“‘16 is the year they talk about, but ‘15 is really the year,” Happ explained. “That group coming together in ‘15, completely and totally outperforming expectations with everybody being new, was what actually set the standard for the organization.”

Cubs’ sneaky good offseason

Ben Verlander and Alex Curry talk about Chicago’s smart moves from this past winter.

After five consecutive last-place finishes, including a 73-win campaign in 2014, the Cubs won 97 games and reached the NLCS in 2015. Now coming off a 74-win season in 2022, it’d be a stretch to expect a 24-win jump and NLCS run this fall. But with All-Star shortstop Dansby Swanson headlining this past offseason’s veteran additions — perhaps this core’s version of the Jon Lester signing — combined with the wealth of young talent knocking on the door, the 2023 Cubs could be primed to surprise the league in similar fashion.  

Rather than potentially leave in free agency right as the organization is turning the corner, Happ will have a crucial impact on whether the next great Cubs team comes to fruition. He’ll also get to keep parking in the front row.

Jordan Shusterman is half of @CespedesBBQ and a baseball writer for FOX Sports. He has covered baseball for his entire adult life, most notably for, DAZN and The Ringer. He’s a Mariners fan living in the Eastern Time Zone, which means he loves a good 10 p.m. first pitch. You can follow him on Twitter @j_shusterman_. 

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