If Cubs’ David Ross conquers these 5 challenges, he’ll manage just fine

First, there is this:

Death to “Grandpa Rossy.”

Not the man, of course, but the nickname. Bury it forever. Shoot it into the sun. Dropkick it into the pits of hell. Just get rid of it.

Cubs president Theo Epstein wants the team to move on from the championship season of 2016, and his new manager’s old nickname is as good a place to start as any. It’s a tired relic, which David Ross certainly is not.

Grandpa? No. Greenhorn? Yes.

Ross, a first-time manager — first-time coach — at 42, is the youngest hired by the Cubs to the position since Jim Riggleman accepted the job a couple of weeks shy of his 42^nd birthday after the 1994 season. Before that, one must travel back to the wake of the 1962 campaign, when Phil Wrigley named Bob Kennedy “head coach” at 42 after the infamous “College of Coaches” gambit.

Grandpa Rossy?

More like Baby Davey.

And another thing: Ross’ magical ascent is — looked at a certain way — over.

Future baseball scholars will ruminate on a man who became an unlikely celebrity toward the end of a 15-year major league career spent almost entirely as a backup catcher. That he became a beloved Cub in 2015, when he hit .176 — it paled in comparison to his robust .184 in 2014 with the Red Sox — is one for the books. That he rose from there to 2016 Cubs glory and on to “Dancing with the Stars” charmer and ESPN analyst is, well, delightful.

It’s as if it was his turn for 15 minutes of fame, only no one remembered to start the clock.

One could argue that landing a managerial gig is just more ascending, and maybe it is, but it’s also an ending or, at least, a drastic change of direction. Ross is the manager of a Cubs team at the mother of all crossroads. Epstein says he was hired on his own merits? Great. He’ll be judged on them — harshly, if the Cubs don’t fly down the road to great success — too.

But say this for Ross, because it’s absolutely true: As a player, he was greater than the sum of his parts and helped make the team greater than the sum of its parts. Epstein stresses the need for the Cubs — 2020 and beyond — to be what Ross the player embodied.

Does he embody it still? The answer hinges on how he fares against many challenges, starting with these five:

1. Ross the boss

Don Kessinger was a five-time All-Star shortstop with the Cubs who, over a long career in the 1960s and ’70s, couldn’t turn around without making a friend. He finished with the White Sox, and when they held a night in his honor in 1978, fans of the Sox and Cubs packed Comiskey Park in equal numbers.

But the Sox named him player-manager — a strange concoction all its own — the next season, and he spent his final days as a player struggling with the realities of leaving pals’ names off the lineup card.

“When you have played with people, it is different,” recalled Kessinger, 77. “It probably was more my fear that there’d be issues with that, than there actually were issues, but it was hard. A lot about the game has changed since then, but that part is something [Ross] will have to deal with.”

Ross was, without question, the most well-liked person in the Cubs’ clubhouse as a player. Those friendships are real. But he hasn’t had to kick Kris Bryant or Anthony Rizzo in the rear end as their boss yet.

David J. Phillip/AP

“Those guys know I’ll be the first to hold them accountable, the first to demand their best daily effort and the first to let them know about it if they give anything but their best,” Ross said in a statement released Thursday. “I never had a problem dishing out a lot of tough love as their teammate, and that won’t change as their manager.”

But the Cubs’ best players — Bryant, Rizzo, Javy Baez, Willson Contreras — aren’t kids anymore. They are, to varying degrees, superstars, and that invites what often are complicated dynamics across all sports. It isn’t 2016 anymore, and Ross won’t be across the room or at a neighboring locker. He’ll be a few hallways and closed doors away.

“He’s my biggest mentor in this game, player-wise, him and [former Cubs coach Eric] Hinske,” Rizzo said. “Can it work? Yes.”

It must.

2. The Jon Lester factor

As the leader of the pitching staff, Lester, who will be 36 on opening day — Ross will have to decide whether or not to give him the ball — is rock solid.

But his ability is fading. There’s no other conclusion after the 2019 season, his worst as a Cub, and 2020 will almost certainly be his last year with the team.

It’s an especially delicate extension of the “boss” section of this story. Ross was Lester’s personal catcher in Boston, where they won a World Series in 2013, and in Chicago. Ross helped Lester in countless ways — steering the pitcher through his yips when throwing to bases (or not) near the top of the list — but what Lester did for Ross’ career is far greater. Lester extended Ross’ viability and relevance in the game.

If Lester falters in 2020, Ross will have to be the one who takes the ball from him in routine starts and, potentially, limits his role when the stakes are highest.

“Obviously, we’ve been through a lot of things together as far as on the field, but off the field we’re obviously good friends, and this deal going forward will definitely be a unique and fun chapter that we’ll get to go through together,” Lester said.

There’s also — again, potentially — the Jason Heyward factor. Heyward and Ross are so close that the outfielder, in appreciation of Ross’ mentorship when they played together in Atlanta, upgraded the catcher’s hotel rooms to suites on the road throughout the 2016 season.

What if Heyward, owner of a giant contract, regresses in 2020 to a repeat of the massive hitting struggles that have dogged him at times with the Cubs? It isn’t as big a concern as Lester — yet.

3. Team building

Twenty-five players, 25 cabs? No, the Cubs aren’t so disconnected that we can apply that old baseball trope.

But Epstein wants — demands — to see his players come together.

“I think with this group, our routines tended to be more individualized,” he lamented after a disappointing 2019 season. “There wasn’t a lot of work as a team.”

Ross’ boss has issued a mandate that the Cubs must work more as a team, have more gatherings — on the field and off — and hear more unified messages from their manager. That means Ross will have to apply his own twists to predecessor Joe Maddon’s petting-zoo breaks and pajama-party flights. Prediction: Those twists won’t involve stuff like, say, petting zoos or pajamas. What Ross does in this regard surely will be harder-edged and more direct, and that’s good — it’s in his wheelhouse.

Mark J. Terrill/AP

Flash back to the last regular-season road trip of 2016 — sorry, Theo — when Ross was at his best. On four straight mornings in Pittsburgh, he corralled Rizzo and strength-and-conditioning coach Tim Buss to work out at a local gym before grabbing lunch together. As the Cubs whiled away the last days in Cincinnati before the start of the playoffs, Ross dragged teammates each morning to a no-frills diner. They talked. They came together.

Especially at the diner, there were some in-your-face conversations. The Cubs were in 108-years-is-enough mode, after all.

It’s at the ballpark, though, where Ross will have to do his most meaningful work in this area. How will he replace a manager who ended that 108-year World Series drought? How will he exert his influence in a manner that dispels any doubts that he’s merely a funnel into which the front office will pour its wishes?

Ross will have to communicate more clearly and directly than Maddon, who trusted players to get the job done. He’ll probably have to be “Grouchy Rossy” on occasion. That’s actually in his wheelhouse, too.

4. Haven’t been there or done that

Ross is as inexperienced as a manager as he was as a big-league hitter the first time he grabbed a bat and headed to the plate. It was 2002, and the Angels’ Aaron Sele was three outs from a 7-0 shutout pf Ross’ Dodgers. Ross had been warming up a reliever in the bullpen when he got word that he was on deck.

He ran in and, heart pounding, quickly struck out. Veteran teammate Erik Karros cracked that there was nowhere to go but up.

A week later, Ross started his first game in St. Louis and caught every pitch of an 11-inning victory. The nerves going into that game were out of control, but Ross was good to go — always would be — once the gear was on and he was squatted behind home plate.

“It’s a very calming, comforting spot for me,” he recalled.

Standing in the dugout for 162 games will be entirely different. Maybe he can take a moment when he brings out the lineup card to squat behind the plate, gather his thoughts and find that calm and comfort?

Epstein believes Ross’ exposure as a player to a bevy of World Series-winning managers — Bobby Cox, Bruce Bochy, John Farrell, Terry Francona, Maddon — adds up to quite a bit of meaningful experience, and that’s wise. Ross, a studious player to begin with, had an Ivy League-level roster of teachers.

But there are decisions a manager must make, especially in the National League, that will come at him in a hurry, and a complexity of puzzle pieces that at times will be difficult to put together. Ross won’t have done any of it before, save for spring training.

When Kessinger was thrust into managing on the South Side, he had a staff he could really lean on. It included Bobby Winkles, who’d managed two big-league teams, and Joe Sparks, who’d managed many of the Sox’ players at Class AAA. The Cubs’ current coaches don’t offer that kind of experience. Ross would benefit from having someone in the dugout with him who has been there before.

5. Being himself

“Grandpa Lossy.”

Sheesh, that didn’t take long.

That less-than-lovable nickname was hung on Ross in a Facebook comment under a Sun-Times story on the morning his hiring became official.

There won’t be much of a honeymoon for Ross the manager, not given the current temperament of the Cubs fan base. They are a cranky, impatient, unforgiving lot. No, not all of them, but far, far gone are the days when anything whatsoever about a poorly performing Cubs team was regarded as lovable.

Just ask Maddon, who, excellent as he was, took shots from all sides beginning with his handling of reliever Aroldis Chapman during the 2016 postseason. But Maddon had a self-generated Teflon skin that enabled him to all but ignore rips from fans and remain pleasant and kind despite the unceasing drumbeat of questions from media.

Ross has no idea what public criticism tastes like, nor has he gone through two-a-day sessions with reporters.

Of all things, this is where he most needs to be like Maddon. As best he can, he must be himself.

But that means much more than keeping his sense of humor. Andy Lopez, Ross’ college coach for one season at Florida, recalls several instances during games when he was about to unload on a player only to find Ross already sitting next to the offender, explaining what he’d done wrong and that it was unacceptable. This right here, this quality — which the Cubs have witnessed countless times — is what Ross is all about.

“We had a great team, with a bunch of [future] major leaguers — a whole lot of alpha personalities,” Lopez said. “But David was in charge. He had that inside of him, that great ability. He is exceptionally knowledgeable about the game, but he also understands the fine balance of it all. That’s in his nature. That’s why I think he’ll be successful as a manager.”

Successful? With this team, at this time, and in front of this fan base, “success” means another World Series. If Ross delivers that, he can have whatever nickname he likes.