Can David Ross fix the Chicago Cubs in his first year as manager?

CHICAGO — An offseason of change for the Chicago Cubs began in earnest earlier this week when the team introduced David Ross to replace Joe Maddon as its manager. The news conference Monday worked to allay the fears of fans on two fronts: Ross’ ability to manage his former teammates and his lack of prior coaching experience.

On the first point, Ross made it clear he wasn’t always the lovable “Grandpa Rossy” he became known as in the late stages of his career as a player, so there’s no reason to believe that’s who he will be as a manager.

“If I would have been mic’d up for some of those conversations on the mound, they were rarely friendly conversations,” Ross said Monday. “The Grandpa Rossy thing is a little bit overblown.”

To point No. 2, regarding Ross’ lack of coaching experience, perhaps there’s a misconception by some that he has been “dancing with the stars” for the past three years. In fact, his work as a special assistant in the Cubs front office, combined with his duties as an analyst for ESPN, have been important in his training for this position.

Ross was in the dugout for 15 years — retiring after hitting a Game 7 home run in the Cubs’ World Series win in 2016 — and was practically a bench coach his final couple of seasons with Chicago. Ross has seen plenty from that perch. Besides, this is 2019. Learning how the front office utilizes information — and how it’s acquired — is critical for a manager these days. And Ross isn’t the only one. NL manager of the year candidate Craig Counsell took the same path as he joined the Milwaukee Brewers‘ front office in 2012 before becoming their manager in 2015 — with no prior coaching experience.

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“The biggest thing that helped me was being in the front office for three years,” Counsell said. “I became more well-rounded as a thinker and someone that was going to be a leader.”

Add Ross’ job for ESPN, in which he traveled the country while observing how other organizations operate, and he almost assuredly has had a better training ground than he could have had wearing a uniform.

“I’ve been in the dugout and know what that’s like from a player and coaching standpoint,” Ross said. “It was a long list, that when I took the special assistant job that [president of baseball operations] Theo [Epstein] presented to me, of things he would like me to check off, and I checked almost all those boxes. … I sat in more meetings than I can talk about.”

The offseason

Will Ross take over an NL favorite in 2020? Hardly. The first thing is the Cubs’ budget: Tamping down offseason spending expectations has become an annual rite of winter. There was a time when the Cubs spent to augment a contending roster, but now the costs are catching up with them, in the form of some questionable signings as well as players entering the later stages of arbitration. Plus, the owner doesn’t believe big spending is all that important.

“The correlation between how much you spend and how many games you win isn’t high enough,” Tom Ricketts said on ESPN 1000 in Chicago this week. “It isn’t going to solve your problem. If you look at this season, we spent more than every other team that made the playoffs.”

The irony of that statement is if the Cubs spent just a little bit more — on a closer in January instead of June — they very well might have made the postseason. Besides, if money had been better spent over the past couple of years, Ricketts’ argument wouldn’t hold water. It comes down to better decision-making, not necessarily spending less. Still, the team has gotten little help from its farm system, so it’s understandable that ownership might look in that direction for some fixes.

“We have to refocus on developing players,” Ricketts said. “We have to draft better. We have to be able to develop players that we bring up because over the next couple years we are going to lose some of the guys. There’s no way that everyone can stay on this team forever because they’re all going to become free agents around the same time. We have to manage that.”

This is the reality the Cubs face: No less than four key players become free agents at the same time, after the 2021 season. That list includes Kris Bryant, Javier Baez, Kyle Schwarber and Anthony Rizzo. Catcher Willson Contreras is one year behind them. That’s the bulk of their championship core.

“Whenever you don’t make [the playoffs], it’s horrible around here,” Epstein said. “That’s not something we want to experience again. Next year is a priority. We have to balance it with the future and that’s probably more important now than it was a year ago because we’re now just two years away from a lot of our best players reaching their end of the period of club control with the Cubs.

“The goal is to do everything we can to win the World Series next year, but we also have to pay attention to the long term and maximize this window while also putting in a lot of good work to open a new one as well.”

Ricketts was even more blunt about windows of opportunity, saying he’d rather just have sustained contention than windows opening and closing over time. The owner also mentioned the benefits of getting under the luxury tax threshold, so it’s going to be very difficult for the Cubs — at least on paper — to look like a World Series contender when spring training opens in February. Many are expecting a retooling year, though the team would never use such terms.

“There are examples of teams that go right up to the end of their contention window with their players and then all of a sudden face a long-term, painful rebuild,” Epstein said. “That’s not something we’re interested in. The art of it will be to maximize all the talented players that we have now and also make sure we’re in really good position for the long term.”

Who stays and who goes?

The Cubs’ strategy is a simple one, as Epstein laid out for all to hear and see. And, no, it doesn’t involve bidding for the elite free agents.

“We’re very likely to engage certain [Cubs] players in discussions about long-term contracts, see if there is a way to extend players’ windows, as Cubs, that way,” he said. “And if that’s not possible, that might make you open-minded about trades. There’s more than one way to take full advantage of a player’s value.”

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In other words, those players who want to stay in Chicago and play ball with the front office have a good chance of getting a contract extension — albeit probably a team-friendly one. Those who indicate free agency is in their future have a good chance of being traded. It doesn’t have to be more complicated than that. That strategy should also serve to restock the farm and turn over the Cubs’ position players, a part of the team that needs an overhaul anyway.

“I don’t believe in untouchables,” Epstein said. “We’re open to change. We’re open-minded about this roster.”

Why change the roster? Chicago’s offense was too susceptible to certain kinds of pitchers. Simply put, those who had great spin would stymie Cubs hitters, though they could mash fastball pitchers. It produced an uneven offense and the front office has finally seen enough.

The three players with the most trade value are Bryant, Baez and Contreras. It’s very possible two of those three will not be on the Cubs next season. And don’t expect a star-for-star deal. This is how the Cubs could retool for 2021 and beyond, by trading for young pitching and position players who might not be major league ready but will be soon.

Of course, if any of those players want to sign a team-friendly contract, the Cubs can be creative and look to make other moves. It’s not that Schwarber and Rizzo aren’t tradable, but both might be more valuable to the team than in the open market, based on the positions they play and the skill sets they possess. In fact, signing both those guys to extensions could give the Cubs some certainty without completely breaking the bank.

It’s the early days of a Cubs offseason bound to make headlines, though not necessarily ones that include Gerrit Cole or Anthony Rendon. Instead, the Cubs will try to fix lingering problems with an eye on the future — and a rookie manager with whom to grow.

“The real key for us is to focus on developing the players that will be our future because you just can’t buy your way into a championship,” Ricketts said. “Teams that signed the big free agents really didn’t move forward this year.”

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