Chicago Cubs: Which team has made the best managerial hire so far?

Several clubs, including the Chicago Cubs, have already wrapped up their managerial searches. Which of these teams made the best hire?

This year’s World Series could, theoretically, wrap up this weekend. Former Chicago Cubs bench coach Dave Martinez has the Washington Nationals two wins away from their first World Series championship, up two games-to-none over the powerhouse Houston Astros with the series shifting back to Washington, D.C. Friday night.

Which means we could be closing the book on the 2019 season relatively soon and turning our attention toward the 2020 campaign. Of course, the Cubs (and fans) did that weeks ago, after the team sputtered to the finish line to cap off a disappointing 84-win campaign.

In recent days, though, Chicago concluded its managerial search, announcing David Ross as the 55th manager in team history. He’ll have his hands full in 2020, as he begins the first season of his three-year contract that includes a team option for 2023.

But Ross isn’t the only new manager to be announced this week. The Philadelphia Phillies made a pretty dramatic shift in philosophy, going with the old-school Joe Girardi to replace Gabe Kapler. Of course, the first managerial hire of the winter? Former Cubs skipper Joe Maddon, who returns to the Los Angeles Angels to breathe life into an organization that hasn’t reached the postseason since 2014 – despite having the best player in the game in Mike Trout.

Given all three men’s ties to the Chicago Cubs, we’ll focus on them for the time being. Which guy is the best fit for their respective organization? Let’s take a closer look.

Chicago Cubs: Maddon returns home, ready to win it all

Some things just make sense. Like Joe Maddon returning to the Angels, the team that originally drafted him and with whom he spent over three decades during his career in professional baseball.

I’ll always be a huge Maddon fan – I mean, how can you not be? The guy ended a century of suffering in Chicago and did it with a flair and gusto rarely seen from big league managers. Still, after the 2019 season, it became pretty clear a time for change had come.

For Maddon, there are no hard feelings and he’s clearly embracing his new team with open arms. It’s a homecoming – and he’s preaching a lot of what we heard when he came to Chicago: he’s going to win and he’s going to do it his way.

“I’m not going to sugarcoat it or pussyfoot around it,” Maddon said at his introductory press conference. “My goal is to be playing [in October]. I don’t like watching this on TV right now. It’s much more fun to be involved. Much more fun to be under the scrutiny, Much more fun to be second-guessed than to not. Never permit the pressure to exceed the pleasure of the moment, ever. When you arrive at that point, that’s when you can really do some special things. That’s what I’m really going to preach this year.”

The Angels have plenty of holes, to be sure. They’re still reeling with the death of Tyler Skaggs and the subsequent fallout that has cast a cloud over the entire organization. On the field, they have some great talents in Mike Trout and Shohei Ohtani, among others, but they’ll have to fill a ton of holes if they want to compete with Oakland and Houston in the American League West.

As happy as I am for Maddon, I’m not sure this marriage will work out quite like everyone involved hopes. The former Cubs skipper, despite his success in the dugout, struggled at times to address non-baseball questions with the media, namely Addison Russell‘s domestic abuse suspension and everything related to it.

We haven’t heard the last of everything surrounding Skaggs’ death – and Maddon better be ready when that foot falls and the questions come flying.

Chicago Cubs: Can Ross bring an edge back to this team?

Unsurprising and expected. That’s about the only way to describe David Ross returning to the Chicago Cubs as the team’s next manager.

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He’s been groomed for this role for the last three years. Even as a player, anyone around him knew that he’d likely have opportunities to return to the dugout down the road in such a role. Now, that time has come and he’ll be tasked with leading the Cubs back to the postseason after the team failed to reach October for the first time since 2014.

Far too many people expect Ross to be some good-natured teddy bear with his former teammates. Sure, he’ll have some fun with the guys – but he’s here to win. Anyone who thinks he can’t hold these men accountable has another thing coming and has clearly bought into the media narrative surrounding ‘Grandpa Rossy.

“Joe often used the word authentic when he described me and the 2016 Cubs,” Ross said in his 2017 book Teammate: My Journey in Baseball and a World Series for the Ages. “He also knew that I didn’t bullshit people. I was straight up with everyone. I was blunt, and at times, a sledgehammer. Joe told me that quality would benefit me if I were to become a manager. But he also always tried to impart on me that ‘honesty without compassion can equal cruelty at times.’ He believed that if I became a manager I would need to lighten the message a bit on occasion.”

So, sure – the Cubs know what they’re getting in Ross. But that’s hardly taking the easy way out or just installing their stars’ buddy as manager. This is a guy who spent his career largely out of the spotlight, doing everything behind the scenes to make himself a better player and teammate.

Chicago made the right call in Ross. He checks a lot of boxes – and he may very well join Aaron Boone, Rocco Baldelli and Alex Cora in the line of inexperienced young managers taking the game by storm.