David Ross is officially moving from "Grandpa Rossy" to "Manager Rossy."
The affable former backup catcher is not only a fan favorite, but he's immensely popular inside the Cubs clubhouse among the core group of players.
However, that popularity has always come in a different form, as he now enters into a new dynamic as Cubs manager. Ross was first a teammate, then transitioned into a front office role with the organization, which included a vital role in recruiting Craig Kimbrel to Chicago.
Now that Ross has been tabbed as Joe Maddon's heir, how will his relationship with the players change?
The Cubs announced Maddon's departure on the final day of the regular season and in turn, immediately stoked the fires of the Ross-as-manager rumors. Players were asked how they'd feel if their former teammate became their boss, including Jon Lester, who was instrumental in bringing Ross to Chicago before 2015 as his personal catcher.
"I think that's something that you'd just have to learn as you go," Lester said. "I would like to think that [former Red Sox manager Tito Francona] was a good friend of mine, but still my manager when it came down to it.
"Obviously the dynamic's different — I didn't play with Tito and that sort of thing, but when it came down to it, that's my boss. If he makes a decision, he makes a decision and you have to respect that."
Anthony Rizzo and Ross formed an immediate bond in 2015 and have grown very close over the last five years.
"If it's Rossy, we would obviously sit down," Rizzo said on the final day of the season. "I've talked to him about it before. He's in a really good place right now at home with his family and what he's doing and he's happy. He's my biggest mentor in the game player-wise, really, behind Joe [Maddon] and [former Cubs coach Eric] Hinske. Can it work? Yes."
Back in August, on the five-year anniversary of his MLB debut, Javy Baez crushed two homers in a Cubs win and after the game, shouted out Ross unprompted. Baez credited his former teammate for helping him understand how to keep things simple and just his natural abilities take over while allowing the game to teach him.
So it's no surprise Baez said in September he would be stoked if Ross were named manager.
"We all love David and he knows the team and the organization," Baez said.
In reality, it will be difficult to transition from teammate and mentor to boss. Maddon found a way to be both mentor and friend to this group of Cubs players, but he obviously never played with any of them and he came to Chicago with an already impressive resume as a manager and coach.
Ross doesn't have that same experience to fall back on, but the Cubs are confident he's up to the challenge because when it boils down it, so much of the job is based off communication.
What Ross has working in his favor that the other managerial candidates like Joe Espada lacked was an immediate rapport with the front office and the core guys in the clubhouse. There's already a built-in level of trust between him and Rizzo, Baez, Lester, Kris Bryant, Jason Heyward and a host of others — including Kimbrel (the two were teammates in Atlanta). The guys he hasn't played with have at least seen him around Wrigley Field or the spring training complex in his front office role the last three years.
That preexisting relationship will be a huge advantage immediately, as it eliminates the time another candidate would've needed to earn the trust of the players on the roster. Plus, the relationship between Ross and Epstein's front office is already so far advanced for a first-year manager that there's an instant level of understanding and rapport before he's even officially introduced into the role.
During his time in the clubhouse, Ross was known to be direct and honest, holding his teammates accountable and helping the young players realize their potential without crushing their spirits. That's not an easy task for a backup catcher in the twilight of his career to accomplish.
Still, the Cubs' choice to go with Ross seemed at least somewhat contradictory when presented against the backdrop of change Theo Epstein emphasized in his end-of-season press conference. The Cubs president talked at length about the organization's need to stop looking back at 2016 and avoiding the "winner's trap" of sticking with things that worked years ago but might not be the best avenues to success today.
In that same presser, Epstein also insisted Ross' connection to the players left over from the World Series championship team was not the main reason they were considering the former catcher as manager.
"His connection to the players on this team and especially his connection to the 2016 team are not necessarily things that are going to be important to us," Epstein said. "...It's not necessarily a detriment, either, as long as you trust the person to handle it the right way and trust the players to handle it the right way. It's something you have to consider.
"I'm just saying, what we're looking for is someone who's a great manager for the Cubs moving forward. Certainly not looking backwards and not with undue emphasis on a couple players there might be a personal [connection]. That's not a major factor for us."
According to David Kaplan, the Cubs have made their decision on a new manager. And to no surprise, they've landed on David Ross.
Highly placed source has confirmed to me David Ross is expected to be named Cubs manager this week. His agent has been discussing contractual terms with Theo Epstein. Deal is almost done. More on @ESPN1000 at 9 am. On @NBCSChicago + https://t.co/VqUFW8rK8r throughout the day.— David Kaplan (@thekapman) October 23, 2019
Cubs made their decision late yesterday afternoon and the other candidates have been informed they are indeed out. David Ross is the choice. @ESPNChiCubs joins me at 9:25 on @ESPN1000. Story coming on @NBCSChicago and the MyTeams app.— David Kaplan (@thekapman) October 23, 2019
Ross was widely speculated as the heir apparent to Joe Maddon and that's exactly how the situation has played out. The team also interviewed incumbent bench coach Mark Loretta, first-base coach Will Venable, Astros bench coach Joe Espada, and former Cubs player and Yankees manager Joe Girardi.
The Cubs had whittled down their options to Ross and Espada, with both candidates coming in earlier this week for a second interview:
Not as formally announced as Espada, but David Ross is said to have also had a second interview with the #Cubs. Given his position with the team, I'm told they expanded conversations earlier this week. #MLB— Kelly Crull (@Kelly_Crull) October 22, 2019
Ross retired after the 2016 season and has spent the last three seasons working in a special assistant role in Theo Epstein's front office while also serving as an MLB analyst/broadcaster for ESPN. He has not coached or managed at any level.
During his two years as a player with the Cubs, Ross was an integral part of changing the culture inside the clubhouse and is revered as a legendary leader to all the young players that came up and helped end the 108-year championship drought. Anthony Rizzo and Kris Bryant affectionately dubbed him "Grandpa Rossy" and he rode that popularity on the shoulders of his teammates in a Rudy-esque celebration after Game 7 and then a stint on "Dancing with the Stars." Every time he has been shown on the video board at Wrigley Field, it elicits a deafening cheer from Cubs fans.
Even three years since he last donned the uniform, Ross' impact remains and the Cubs have been searching for the type of clubhouse leadership he provided. Earlier this season, Javy Baez brought up Ross unprompted, mentioning how Ross told him that this game teaches you something new on a daily basis.
The question was never really if and more about when Ross was going to get a chance to manage the Cubs in the future. Just last fall, he was brought up as a potential option to replace Brandon Hyde as Maddon's bench coach, but Ross still wanted to spend time with family in retirement and wasn't yet ready to commit to the grind of a long season.
Still, Epstein mentioned at the GM Meetings last November that he and the front office were pushing Ross to be around the team more in 2019. GM Jed Hoyer followed that up at the Winter Meetings in December talking about how much of an impact Ross has on these players and the level of trust that's already inherent within this group.
Apparently, Ross is now willing and able to put in the 7-to-8 month time commitment to step in as the Cubs' new manager. When it was officially announced Maddon would not be returning, Ross was on ESPN's Baseball Tonight and expressed interest in the job and Epstein confirmed the next day Ross was on the team's list of managerial candidates.
Epstein mentioned he would prefer hiring a manager with big-league experience and the main theme of his end-of-season press conference was all about change, not hanging their hats on 2016 and climbing out of the "winner's trap." But they still opted for Ross as the organization's new field general.
"I always have greater comfort level hiring for roles in which the person has done the role before, especially with manager," Epstein said on the final day of September. "I think there are ways for that to be overcome. There’s a lot of different ways to get experience in this game. Beliefs, skills, personal attributes, those can outweigh a lack of experience, but experience certainly helps.
“David Ross has a lot of great things going for him, I would say. His connection to the players on this team, and especially his connection to the 2016 team, are not necessarily things that are gonna be important to us.
“I think Rossy is a really attractive candidate, and he’s gonna be evaluated on the merits, what he can bring to the table as a major league manager given his skills, given his experiences, given his world-view, given what he knows about winning, all those things.”
We now know how that evaluation process has played out.
The question now becomes — how would the Cubs players handle Ross as a manager, moving from friend and teammate to boss?
We'll find out in the coming months.