The Cubs hired Ross as a special assistant to their front office in early 2017 following his retirement after a 15-year MLB career. While Ross spent plenty of time around Cubs executives Theo Epstein and Jed Hoyer in the past three years, his presence around the team really increased beginning in spring training this past February.
That continued throughout the season, evidence that the club was preparing him for the managerial job.
Generous as ever, former Cubs manager Joe Maddon took Ross under his wing during spring training. Maddon spent a handful of Cactus League games explaining his baseball beliefs and giving advice to Ross.
At the same time, Ross was better familiarizing himself with the Cubs coaching staff. He had already worked with or under many of the coaches previously, but he got to know them better in this time.
Ross, 42, carried the reputation of being a great teammate during his playing career. He understood when to listen, when his voice needed to be heard and the approach it took to reach a teammate.
That's a big reason why the Cubs signed Ross ahead of the 2015 season. They added him to be ace Jon Lester's personal catcher, with Epstein and Hoyer understanding that Lester could need some special handling in a new environment from someone who understood him.
Many thought Ross wouldn't provide much value as a light-hitting catcher who handled one pitcher, but he became much more for the Cubs. Soon, other Cubs players were hanging around Ross' locker and receiving the baseball education that he was offering. Ross was never shy about handing out tough love. In one postgame scene, Ross confronted fiery veteran pitcher John Lackey face-to-face regarding what hadn't worked in Lackey's start that day.
"You need to know the man and what makes him tick when you get into another teammate's grill," Ross said back then. "John is all about excellence that day. He is a great teammate on those other days, a terrific guy. You must understand the warrior on that day he pitches or plays. You build that with time put in and loving care. Tough love is a byproduct of a relationship built that can withstand that tough moment."
Ross had the strong communication skills that the Cubs are looking for. And if his playing career was any indication, he'll be plenty comfortable handling the media spotlight, which is a big responsibility in a market like Chicago.
In the Cubs' mind, it all adds up to Ross being the best individual to create the culture they want and get back to their winning ways after missing the playoffs in 2019.
"Theo believed that if an organization could create a culture where players knew they were being told the truth, it would be a big competitive advantage," Ross wrote in his book "Teammate," which was published in 2017. "He felt that would help nurture relationships and a great environment where players could relax and be confident around themselves and management. Put building trust and acting with integrity on the same level as winning."