It was August 2019, still a couple of months before David Ross would be introduced as the 55th manager of the Chicago Cubs. It also was the day before the Alabama Crimson Tide football team would begin practice.
Alabama head coach Nick Saban had asked Ross to speak with his team about the one thing Ross knew more about than anything — being a good teammate, hence making it the title of Ross’ book. And Ross wasn’t going to pass up his own opportunity, to learn from one of the best in any leadership role. Ross knew he wanted to be a manager someday and who better to pick the brain of than one of the best college coaches of all time.
“I got about 30 minutes in his office, alone,” Ross said recently of Saban. “Just talking about sustained success. That constant drive.
“He never takes for granted the success he’s had. He’s always looking forward. What’s new? What’s to come? Where are their faults? Where can they improve, rather than focusing on the success they’ve had. That stood out to me.”
It might have stood out because it applies to the team Ross would take over later in 2019. It wasn’t long ago that the idea of sustained success was a foreign concept on the North Side of Chicago, but after winning the World Series in 2016, the Cubs had failed to regain their mojo, their edge, their eliteness. The result was a change in managers and “threats” from the front office to break up their core players. In stepped Ross, who has been on a mission to learn.
And learn he has. From Aaron Boone on the interview process and even tips about going to London to Alex Cora on juggling managing and family. Dave Roberts gave him advice on the delicacy of hiring and firing coaches. A private meeting with Joe Torre at the winter meetings was an education in and of itself. And of course, there was his predecessor; no one has been more kind and gracious than Joe Maddon.
“I even picked Bernie Williams’ mind on a private flight to Maddon’s charity event late last year,” Ross said. “I’ve just tried to talk with everyone. Maddon has been great. I’ve learned so much from him and others. Some of which I’ll take with me into my new job.”
Before Ross would engage with any of his managerial brethren, he was standing before the Alabama football team. By then, Ross had spent time with Saban in his office and knew what the coach wanted him to impart to his team, according to another person in the room.
“It was a room filled with a lot of guys with NFL hopes, and the assignment for David was to get them ready to begin the season as better teammates for each other,” said Don Yeager, the co-author of “Teammate,” Ross’ book. “Saban had identified a little selfishness as one of the reasons the team flamed out in the national championship game the year before against Clemson.”
Yeager said one way Alabama tracks effort is with electronic devices implanted in equipment worn by players. The numbers interpreted by the devices went down late in 2018, and Saban took notice. This perennially elite program was wavering a little.
“You can climb to the top of the mountain and it’s a quick decent if you let it,” Ross said. “You have first-rounders left and right in that program. My job was to help stars become role players.”
This was part of the conversation in Saban’s office, before Ross spoke with the players.
“No matter how well things are going, if you’re not bringing your full and very best at every stop, the competition keeps getting better and you can’t just turn it back on,” Yeager said. “It was a really powerful discussion.”
They are different sports with different types of athletes — from their ages to their skill sets –but that concept wholly applies to the Cubs, a team full of stars who were not better as the sum of its parts over the past couple of seasons. The speech Ross gave to the Crimson Tide players might not be that different than the one he gives to his own team next month.
“We are always looking for ways to improve our team and the leadership within our organization,” Saban said via email. “David spoke to our team … and did a fantastic job of stressing the importance of being a good teammate and how building those relationships in the locker room only enhance the performance of your team when everyone challenges each other. I know David will do a great job of leading the Cubs organization.”
But remember, Ross had ulterior motives when visiting Alabama. He wanted to learn from Saban as much as Saban wanted him to teach his players about being a good teammate. The half an hour spent in Saban’s office was eye-opening.
“The button that closes the door is real,” Ross said with a laugh. “You walk in and the door closes. Everything is scheduled to a T. We went down about three flights of stairs, and at every door there was someone, knowing he was coming, holding the door open. This guy is to the minute.
“He was so involved in the coaches. That’s something I’ll take from that. It was cool to see him coaching and not just delegating. It was the first day, but he got right in the middle of everything.”
It would be something Aaron Boone would echo to Ross later: Be involved. Meanwhile, back in Saban’s office, Yeager was busy observing Ross picking the coach’s mind.
“I was watching him processing all this,” Yeager said of Ross. “And we were just there on a speaking engagement, but he’s taking notes and writing things down. It was an awesome, very raw conversation.
“David asked Saban, ‘Given all that you experienced, what happened last year that you were so great for so long but flamed out on the national title stage.”
The answer reflected back to why Ross was there in the first place: to remind a group of elite players why it is important to be unselfish as teammates. It can be the difference between winning and losing.
Ross chuckled at his final recollection of his day with Saban.
“At the end I said, ‘I don’t want to take all of your time.’ He said, ‘You’re not. You have three minutes left.'”
The similarities between Ross and Boone are hard to miss. Both are somewhat recent retirees from playing, and both came down to manage from the broadcast booth without any previous coaching experience. Unlike Boone though, Ross had three years in the Cubs’ front office prepping him in a different way than the old-school path of coach to manager. Considering Ross’ time as a backup catcher was spent as a coach of sorts, as well, some found it laughable when the Cubs were criticized for hiring someone without experience. Ross has plenty.
“There’s a lot of ways to skin a cat and a lot of ways to gain valuable experiences,” Boone said in a phone interview. “Teams are smartly trying to find their best person for the job, from wherever that is. Instead of checking a couple boxes and only going that way, teams are finding good leaders from different places.”
The early success Boone has had with the New York Yankees also has helped take away some of the stigma that “first-time manager” had in front offices.
“I talked to Boone both before and after the interview process,” Ross said. “Just about all those little things. I probably talked to him the most.”
So what was the advice?
“You definitely have to prioritize and identify each and every day as things you want to touch,” Boone explained. “What do you want to be involved in? I think it’s important to have something you dive into a little more specifically, something you sink your teeth into.”
For Ross, the presumption would be working with his catchers. As good as All-Star Willson Contreras is, he still hasn’t reached max potential in some of the finer points of catching, from calling a game to framing.
“It connects you to the club,” Boone said of getting your hands dirty as manager. “It connects you to your coaching staff. And I think it’s invigorating and important.”
Boone’s best advice for a new MLB manager is to expect the unexpected. As players, their world was so small — as compared to their world as managers. You just have to assume your day won’t always go as smooth as you’d like, according to the Yankees skipper.
“The unknown,” Boone said. “You’re dealing with upwards of 50, 60 people, including clubhouse staff and players and families. You’re dealing with people here. Things come up.”
Ross wasn’t done with Boone. After getting the job and learning about some of the bigger issues facing a manager, they dove into some of the finer details, even discussing the Yankees’ trip to play the Boston Red Sox in London last summer. The Cubs will make the same journey this June, facing off against the St. Louis Cardinals.
“I said it was kind of like the Super Bowl,” Boone recalled. “It is a lot, but our guys really embraced it. The travel does zap you a little bit. And because you have those off days built around it, the rest of the season can be a challenge because you have less off days at other times.
“To a man, we really embraced and enjoyed it.”
Perhaps the most surprising and rewarding conversation Ross had this winter was with one of Boone’s predecessors with the Yankees who is now Major League Baseball’s chief officer.
“He asked to have a meeting, in this gigantic boardroom,” Ross said of Torre. “I figured it was for all the managers about rules or umpires, so I walk in and Joe walks in and it was just us.”
Torre simply wanted to lend a hand to another former player-turned-skipper. Ross wasn’t going to pass up the chance.
“He went straight from being a player to a manager and knows how close I am to those [Cubs] guys,” Ross said. “He gave me some great advice, balancing information from the way I was brought up with the way the game has changed.”
Torre gave the same input Ross has heard often this winter — from his bosses and Maddon and Boone.
“Good outcome or bad outcome, you won’t be happy with yourself if you don’t stay true to yourself,” Ross said. “Torre told me I’ll sleep a lot better at night if I’m true to myself.”
It sounds like simple advice, but Boone said “early on” that can be tough, because you’re getting pulled in so many directions.
But mostly Torre’s advice revolved around players.
“He told me some great stories about Cecil Fielder and Darryl Strawberry, about how you deal with players,” Ross recollected. “Probably some I can’t share. You have to shoot them straight. They want the truth, no matter who they are, from 25th man to a role player to a minor leaguer.”
It is the same message Maddon often cited when Ross was playing for him in 2015 and 2016: Tell a player a tough truth and he might dislike you for a day or two; lie to a player and he won’t ever respect you again. Ross has preexisting relationships with several Cubs stars, but he views that as a positive, not a negative. They know he is coming from a caring place, so an honest truth might not hurt as much.
“Good outcome or bad outcome, you won’t be happy with yourself if you don’t stay true to yourself. Torre told me I’ll sleep a lot better at night if I’m true to myself.”
David Ross on the advice Joe Torre gave him about managing
“He’s had so much success in the game but also some failures,” Ross said of Torre. “As helpful and open as you could ask for. Most successful guys talk about their failures more than their success.
“Talking to Joe Torre was my favorite thing I did at the winter meetings.”
The Cubs’ new bench coach was a curious hire at first glance. It was smart to bring on a former National League manager to help. But many figured it might be more of a grizzled veteran such as Fredi Gonzalez or even former Cubs manager Jim Riggleman, instead of someone who is actually four months younger than Ross. But Green and Ross have hit it off immediately, with the latter relying heavily on the former’s recent experiences as San Diego Padres manager from 2016 through last season. Green’s record (274-366) wasn’t great, but remember the concept of learning from failure?
“When I first got the job in San Diego, I was on planes flying all over the country, meeting everyone as fast as possible, running myself into the ground, trying to do things immediately like it had to be done yesterday,” Green said recently. “I told [Ross] you didn’t have to do everything.“
It actually was antithetical to what Ross was thinking as a guy who likes to talk things out. In fact, the transition from Maddon to Ross won’t be much a change for reporters, as both can fill up a notebook. But Maddon realized when it came to players, less is often more. He had fewer team meetings than most and shorter conversations with players, but in taking over, Ross figured he needed to talk — with everyone.
“Green told me he reached out to everyone and almost overcommunicated and realized that may have backfired on him,” Ross said. “You have to earn it, so to speak. It was nice to hear from him. Little things like that, he’s helped out a ton with.”
Green and Ross also have been discussing strategy, like how to handle the new rule regarding a three-batter minimum.
“The good thing is he will have never managed the other way,” Green said of Ross. “His first instincts will have this rule in mind from Day 1.”
The parade of advice didn’t stop there. Conversations with Alex Cora, Dave Roberts, Davey Martinez and others produced insight Ross will tap into when needed. In fact, there might only be a handful of current managers he hasn’t talk to.
“Davey [Martinez] and I talked about having those struggles [in 2019] early on, then coming on at the end,” Ross said. “How to weather that storm.
“I have so many people. Gabe Kapler texted me the other day. [Clemson Tigers football coach] Dabo Swinney and I have exchanged text messages a while back. He kind of had a big game coming up, so I haven’t talked to him … I’m going to ask him a lot about delegating to the coaching staff, as well.”
The education never stops in baseball, especially for a first-time manager taking over an iconic franchise. The Cubs have talent that has underachieved at times since winning the World Series. It is Ross’ job to bring it out of them again — but this time not as their teammate or even their friend. And despite all the advice and kind words — from Saban to Torre and all the others — Ross is cognizant of being his own man. He will be the one judged, not those who gave him advice.
And Ross will inherit a fan base that loves him but also is antsy, to say the least. For two winters now, the Cubs have done nothing to change the dynamic on the roster while seeing wins and playoff appearances become harder to achieve. The latest blow was losing Nicholas Castellanos — an instant fan favorite last summer — to the division rival Cincinnati Reds. Add that to the slew of relievers the Cubs had to pass on, due to budget restraints, and Ross wouldn’t be wrong in thinking he has to do this himself. It’s on him to get more from what has been less.
“I also want to go in with a clean mind and assess things for myself,” Ross said. “I’m ready.”