On December 15, 2015, Heyward signed an eight-year, $184 million contract with the Cubs.
One of his first acts after signing his contract was to pay for hotel suites large enough to accommodate teammate David Ross, his wife, and their three young children on all of the Cubs' road trips during the 2016 season.
Ross, set to retire after the 2016 season, had been Heyward's teammate during his first three seasons in Atlanta, and Heyward considered him a key mentor in his early MLB career.
In an interview with the Bleacher Report website, Heyward said,
I know how special it is to have teammates like he was my first three years in Atlanta.
You don't take it for granted.
I wanted to say thank you from the bottom of my heart, as a teammate and as a friend, for what he's done for me.

Heyward struggled in his first season with the Cubs in 2016, batting only .230 with 7 HRs and 49 RBIs, while leading the majors in percentage of soft-hit batted balls (27.1%), though he would win his 4th Gold Glove award that season.

In Game 4 of the 2016 National League Division Series against the San Francisco Giants with the Cubs having a 2-1 series lead, Heyward reached on a bunt force out and moved to second on an errant throw.
He scored the go-ahead run on a Javier Baez single, sending the Cubs to the National League Championship Series.

On October 25, 2016, Heyward, along with teammates Dexter Fowler, Addison Russell, and Carl Edwards Jr., became the first African-Americans to play for the Cubs in a World Series game.
Heyward was credited with leading an inspiring players-only meeting during a 17-minute rain delay near the end of Game 7 of the 2016 World Series.
The Cubs eventually won the game 8-7 after 10 innings, and gave them their first World Series championship in 108 years.
On November 9, Heyward became the first position player in Major League Baseball history to win three straight Gold Glove Awards with three different teams (Braves, Cardinals and Cubs).
On December 15, 2015, Heyward signed an eight-year, $184 million contract with the Cubs. One of his first acts after signing his contract was to pay for hotel suites large enough to accommodate teammate David Ross, his wife, and their three young children on all of the Cubs' road trips during the 2016 season. Ross, set to retire after the 2016 season, had been Heyward's teammate during his first three seasons in Atlanta, and Heyward considered him a key mentor in his early MLB career. In an interview with the Bleacher Report website, Heyward said,
I know how special it is to have teammates like he was my first three years in Atlanta. You don't take it for granted. I wanted to say thank you from the bottom of my heart, as a teammate and as a friend, for what he's done for me.
Heyward struggled in his first season with the Cubs in 2016, batting only .230 with 7 HRs and 49 RBIs, while leading the majors in percentage of soft-hit batted balls (27.1%), though he would win his 4th Gold Glove award that season.
In Game 4 of the 2016 National League Division Series against the San Francisco Giants with the Cubs having a 2-1 series lead, Heyward reached on a bunt force out and moved to second on an errant throw. He scored the go-ahead run on a Javier Baez single, sending the Cubs to the National League Championship Series.
On October 25, 2016, Heyward, along with teammates Dexter Fowler, Addison Russell, and Carl Edwards Jr., became the first African-Americans to play for the Cubs in a World Series game. Heyward was credited with leading an inspiring players-only meeting during a 17-minute rain delay near the end of Game 7 of the 2016 World Series. The Cubs eventually won the game 8-7 after 10 innings, and gave them their first World Series championship in 108 years. On November 9, Heyward became the first position player in Major League Baseball history to win three straight Gold Glove Awards with three different teams (Braves, Cardinals and Cubs).
Jason Heyward