The Jason Heyward trade (Nov. 17, 2014)

The trade: The Braves traded Heyward and RHP Jordan Walden to the Cardinals for RHP Shelby Miller and RHP Tyrell Jenkins.

How it happened: If there’s one player on this list who most closely matched Machado when he was traded, it’s Heyward. He was 25 years old when he was dealt, the same age Machado is now. Heyward had a career 24.6 WAR; Machado’s is 27.9. And while Heyward didn’t have Machado’s power, he was better at getting on base and a much better runner. Both Heyward and Machado are elite defenders, having won two Gold Gloves apiece by age 25.
The Braves were in full rebuilding mode when they sent Heyward to St. Louis. The key return piece was Miller, a pre-arbitration righty who’d spent two full years in the Cardinals’ rotation and had a career 26-18 record and 3.33 ERA. The Braves also threw in veteran reliever Walden and received Jenkins, a lower-level prospect.

The results: The Cardinals got exactly what they hoped for out of Heyward, who batted .293 with a .797 OPS and collected his third Gold Glove, helping St. Louis win 100 games and the NL Central in 2015. The Cardinals, though, lost the Division Series to the Cubs, who then signed Heyward as a free agent that winter. The Cardinals received a compensatory draft pick for losing Heyward, which they used on righty Dakota Hudson, currently ranked their No. 9 prospect by Baseball America.

Meanwhile, the Heyward trade is the gift that keeps on giving for the Braves. Miller spent one year with Atlanta and pitched quite well, registering a 3.02 ERA in 32 starts — although he led the majors with 17 losses because the team around him was terrible.
The Braves were able to parlay that into a mega-deal with the Arizona Diamondbacks after the 2015 season, acquiring former No. 1 overall draft pick Dansby Swanson and outfielder Ender Inciarte for Miller. Swanson struggled in 2017, but is just 23 and could be Atlanta’s shortstop for years to come, while Inciarte has already racked up two Gold Gloves and an All-Star appearance in two years with the Braves. Miller, meanwhile, collapsed to a 6.15 ERA for Arizona in 2016 and underwent Tommy John surgery in 2017.

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