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Watch Cubs’ extension talks with Javy Baez, interest in Japanese CF Shogo Akiyama for 2020 insight

As the Cubs balance a priority of extending their competitive window with trying to win in 2020, almost every part of the roster is in flux.

Japan v MLB All Stars - Game 4
Shogo Akiyama, hitting against a team of MLB All-Stars last year, is on the Cubs’ radar as a potential solution to center field and the top of the order.
Photo by Kiyoshi Ota/Getty Images

SCOTTSDALE, Arizona — The Cubs plan to consider options as far away as Japan and as close as rookie Nico Hoerner in retooling their roster for 2020 and — in their best-case scenario — an extended competitive window.

In the meantime, they left the annual general managers meetings Thursday in greater flux and at a bigger crossroads than team president Theo Epstein has faced perhaps in his 17-year career as a top baseball executive.

In moving on from decorated celebrity manager Joe Maddon, the Cubs restart next season with a first-year manager, new-look coaching staff and a roster that, well, who knows?

With the first round of intelligence gathering out of the way, indications from the Cubs suggest a team that still has 10 players left from its 2016 championship could see changes as radical as trades of stars such as Kris Bryant and Willson Contreras, or as small as a few pitching and outfield tweaks and some maneuvering with a tight payroll.

“I don’t know what this winter is going to look like,” Epstein said. “I know what an ideal world looks like. In an ideal world, you can enhance your major-league team and put a really compelling product out there and the team has a legitimate chance to win the World Series and also take legitimate steps towards ensuring your future and making sure there’s not that big of a drop-off in 2021.”

Anyone banking on that scenario for the Cubs might get more out of skipping the winter meetings next month in San Diego and driving the 95 miles north to Disneyland instead.

Splash Mountain is bigger than any splash they’re positioned to make in free agency. And help from the farm system in 2020? Talk about Peter Pan’s Flight.

“There’s probably a series of moves we could pull off that would bring that about, and it won’t be easy,” Epstein said. “You normally have to make sacrifices one way or the other and operate in a world where there are real trade-offs.”

And this winter, just plain trades, whether they’re more payroll-related or for purposes of getting the controllable players to create that extended window.

“We’ll just have to see what’s available to us,” Epstein said. “This is just the start of that process, really, seeing what realistic paths we can take — not sort of the idyllic paths we try to create in our mind.”

Did somebody say Disneyland?

Gaze far enough west, and it’s not hard to imagine Maddon indeed landing in the Happiest Place on Earth with the Angels, in the Anaheim shadow of Mickey Mouse.

Maddon has the best player in baseball in center field, two-way star Shohei Ohtani ready to pitch again in 2020, an owner spending money this winter and California sunshine in April.

The Cubs have no idea who their center fielder or leadoff hitter will be; Epstein said this week that Tyler Chatwood is a candidate to return to the rotation; their budget is hamstrung by bad contracts; and April at Wrigley . . . never mind.

Not exactly Mike Trout, Ohtani and a wheelbarrow of cash.

Hey, at least Chatwood can hit a little.

In fact, as the business of the offseason begins to accelerate, Chatwood is only one of several players to watch for signals of whether new manager David Ross has the roster to keep up with the Cubs’ last manager, which includes:

Javy Baez

The two-time All-Star shortstop and 2018 MVP runner-up already has begun negotiations on a potential long-term extension with the Cubs, according to sources. It’s the first big step in knowing what their financial landscape might look like not only for this winter but for planning their strategy for the next several years.

A deal is considered much more feasible to reach with Baez than with Kris Bryant, the team’s other high-profile superstar within two years of free agency. That doesn’t mean the Cubs will suddenly trade Bryant if they can’t reach an agreement with him — especially if they get agreeable terms with Baez. But it certainly would keep Bryant’s status in play throughout the winter, then possibly at the trade deadline and again next winter, barring a move before then.

Shogo Akiyama

The 31-year-old Japanese All-Star center fielder is a free agent with a .400-plus on-base pedigree in Japan. He’s “a great hitter,” according to Cubs pitcher Yu Darvish, who faced him early in his career in Japan.

The Diamondbacks have been linked to Akiyama, but he’s one of at least two Japanese free agents on the Cubs’ radar — and by far the better fit for a team making a priority out of both his position and his skill set at the plate. Even at an estimated price tag that might be as reasonable as $5 million or so per year for maybe three years, it could make a full-speed pursuit something the Cubs have to put on hold until gaining more clarity with their payroll flexibility.

Tyler Chatwood

The Cubs have four returning starters in their rotation, depending on whether they trade Jose Quintana or somebody else. Chatwood was signed two years ago to a three-year, $38 million contract to be a starter — until a disastrous 2018 season and demotion to the bullpen.

He and Alec Mills are considered in-house options in 2020, and Epstein said the team plans to explore some of the second-tier starters on the free-agent market. “Its an area that’s fairly robust this year, the depth of free-agent options,” he said. “Maybe even more so than the relief market. It’s usually the other way around. I think you have to be open-minded.”

Craig Kimbrel

With the Braves’ signing of Will Smith Thursday (three years, $39 million), the free-agent market lost its only true reliable closer. Kimbrel, who has two years and $33 million left on his contract (and a limited no-trade clause), did not look good for the Cubs after a midseason signing last year, especially down the stretch.

But he appears to be healthy, and the seven-time All-Star might draw some unanticipated interest from teams in need. The big question will be whether it’s enough to dislodge his salary from the payroll.

Either way, the bullpen is a “priority” for the Cubs, who could get a low-risk, high-reward fix if Brandon Morrow stays healthy and returns on a minor-league deal.