Remember Some Cubs: Jason Heyward, the Current Record-Holder of the Biggest Contract in Cubs History

Before we dive into the nitty-gritty of Jason Heyward’s time with the Cubs, I want to note that this article (and others like it) is done in conjunction with North Side Baseball’s Chicago Cubs Players Project. It’s a wiki-style project that anyone—including you, dear reader—can contribute to. There, we’re chronicling the careers of every player who’s ever put on a Cubs uniform (including, for example, Mike Olt), and adding any personal memories or particularly favorite experiences fans have from that player’s tenure. It’s a community project, and we hope you’ll contribute to it.

Jason Heyward, known cheekily as “The J-Hey Kid”, was a first-round pick (14th overall) of the Atlanta Braves in the 2007 MLB Draft. He began his minor-league career at just 17 years old, appearing in three minor-league All-Star games and winning two Minor League Player of the Year awards. By the time 2010 rolled around, multiple media outlets named Heyward the top prospect in baseball. He won the Braves’ right-field job as a 20-year-old rookie that year, making his debut on Opening Day against the Cubs. His first at-bat proved to be a memorable one.

That home run proved to be a positive omen, as Heyward went on to earn an All-Star nod as the National League’s starting right fielder during his rookie campaign (though he would miss the festivities due to a thumb injury). That would actually be the only All-Star honor in Heyward’s career (er, so far), though he continued to produce at an above-average level for years. In his first five seasons in Atlanta, he racked up 23.0 bWAR, slashing .262/.351/.429 (117 wRC+) while winning the first two of five career Gold Gloves.

In Nov. 2014, just one year out from free agency, Atlanta dealt Heyward to the Cardinals, for a package highlighted by Shelby Miller. For Atlanta, the hope was that they'd find a long-term ace. For St. Louis, Heyward had to replace the tragically deceased Oscar Taveras. Heyward thrived in his lone season in St. Louis, accruing a career-best 6.9 bWAR and hitting for a .797 OPS (122 wRC+) in 2015. After losing to the Cubs in the NLDS, Heyward deemed their future to be bright and the money to be right; he joined the franchise in free agency. It remains the largest deal in Cubs history (for now): $184 million, spread out over eight years.

At this point, a lot of emotions will bubble to the surface. Heyward was, for all intents and purposes, not worth his contract in terms of on-field production. Though he won his final two Gold Gloves in 2016 and 2017—and continued to provide stellar defensive value after, totaling 35 Fielding Run Value (FRV) in his time in Chicago—he was a disaster at the plate. From 2016-22, Heyward slashed .245/.323/.377 (88 wRC+)—which, I have to be honest, is significantly better than I remember. Over the four-year stretch from 2017-20, Heyward actually posted a .752 OPS, which, when coupled with his defensive skills, made him worth 8.2 bWAR. Is that good enough for a guy getting paid $23 million per year? No, but it was only in the final two years of his time on the North Side that he really fell off (-0.3 bWAR, 67 wRC+). That was all after a truly lost 2016, though, too.

Of course, his most memorable moment with the Cubs didn’t even happen on the field. During Game 7 of the 2016 World Series, Heyward gave the famous “Rain Delay Speech” during the 17-minute, weather-induced intermission before extra-innings began. He rallied a team that had just squandered a three-run lead with four outs to go, and the Cubs returned in the top of the tenth to bring home two runs, including the lead-taking RBI by World Series MVP Ben Zobrist.

Heyward batted just .150 in that World Series (and had a sub-.350 OPS in the 2016 postseason), but that speech defined his Cubs legacy. Sure, the Cubs would have liked to get some more production in the ensuing seasons, but that was a $184 million speech, and it was worth every penny. Heyward was a model citizen away from the game, and served as an invaluable mentor to the team’s young players once the World Series core was traded away. While it can’t be ignored, Heyward’s bat was the only thing that lagged behind during his time with the Cubs.

Toward the end of the 2022 season, Jed Hoyer confirmed that Heyward would be released. He took a one-year deal with the Dodgers in free agency and had his best season in years while serving as part of an outfield platoon for the NL West champs. He re-signed with Los Angeles for the 2024 season, though he was released in August. He joined the Houston Astros for the stretch run, posting a .756 OPS in limited work for the best team in the AL West. Heyward will be awarded a ring for his services with the Dodgers in 2024, and he is currently a free agent.

It’s possible that Heyward’s playing career has come to an end. If so, he’ll be remembered with bittersweet fondness for his time with the Cubs, who probably don’t win that 2016 championship without him.