This could be the end of the line for a controversial former Cubs outfielder

At 35 years old and limited throughout the 2025 season, former Chicago Cubs Gold Glover Jason Heyward faces uncertain prospects about continuing his playing career after being designated for assignment by the San Diego Padres on Saturday.

On the IL for knee inflammation at the time of the move, Heyward has struggled with the Friars, slashing just .176/.223/.271 in 95 trips to the plate. Now, San Diego has a week to either trade the veteran outfielder or pass him through waivers. Should he clear waivers, given his service time, he can accept an outright assignment to the minors or hit free agency.

It's hard to imagine many teams would have interest in his services given the injury concerns and general lack of production. Heyward is no longer the elite defensive presence he was for much of his career and he's been an above-average offensive player (using OPS+) just one time since 2021. He's had some solid seasons, most notably with the Los Angeles Dodgers in 2023, but he's lost a step and I don't see a team giving him more than a minor-league deal at this point.

Cubs fans, to this day, have strong feelings about Jason Heyward

Cubs fans are intimately familiar with Heyward who, following a monster 2015 season with the rival Cardinals, signed an eight-year, $184 million deal with Chicago which, to this day, remains the largest free-agent contract in franchise history. If not for his locker room speech that rallied the troops during the Game 7 rain delay, he'd go down as the biggest free agent bust in Chicago sports history - and even with it, his Cubs tenure is still wildly divisive and always draws strong reactions from fans.

During his seven years with the team, he never mustered even one 3.0 bWAR season - although he did bring home a pair of Gold Gloves in his first two years in Chicago. It's not that he was a bad player, he wasn't. But he never came close to living up to the hype and expectations that come with a contract like that - and that's the lens most of the fanbase views his time with the Cubs through.

So, if this is the end of the line for the 16-year MLB veteran, he's had quite a run. An All-Star, a five-time Gold Glover and a World Series champion - not to mention one of the game's best human beings. Not a bad legacy - and the $210+ million in the bank doesn't hurt, either.