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Meetings expectations? Cubs roster open for business as Theo and Co. head to winter meetings

The Cubs have hired a new manager and coaches and restructured the player development and scouting departments. Heads up, Kris Bryant and Willson Contreras — that could only be the start of a very busy offseason for the club.

Chicago Cubs Introduce David Ross - News Conference
Cubs president Theo Epstein with newly hired manager David Ross
Photo by David Banks/Getty Images

Is it the Cubs’ turn yet?

Is Chicago’s big-boy baseball operation ready to join an already bustling winter player market and start working on its actual roster after two months manager and coaching changes and overhauling its player development structure?

Team president Theo Epstein certainly fueled speculation even before October by vowing that the Cubs planned a busy winter that would be approached with an “open mind” when it came to any and all its players.

And speculation since then has involved the Cubs listening to trade overtures from other teams regarding every core player from the usual big name (Kris Bryant) to, more recently, the almost unimaginable (Anthony Rizzo).

Don’t expect the Cubs to exactly blow up the roster, even as they shift direction with first-time manager David Ross. But don’t expect them to keep all the fan favorites from what’s left of that 2016 championship core, either.

So far the biggest roster move they made was to cut ties with polarizing infielder Addison Russell.

But they could be especially poised for an active winter meetings over the next week in San Diego.

For one thing, the free agent market not only is moving far more quickly than in the past two years, but that early activity has started to shape position markets that could have a direct bearing on some of the Cubs’ needs and potentially available players.

Already, when the Phillies signed right-hander Zack Wheeler away from the pursuing White Sox at midweek, it meant five of top 18 free agents (per MLBTraderumors.com) had been snapped up for a total of $315 million and 17 years worth of contracts.

And then the free agent pool only got more interesting – and deeper – during the week when a staggering 54 more players were non-tendered by their teams at the deadline for declaring intent to offer contracts to controllable, unsigned players.

That could play to the Cubs’ need to add net talent and depth without adding much if any net payroll.

Some of the important questions the Cubs are trying to answer as they head to the winter meetings and get down to the business of trying to extend a would-be championship window while trying to avoid a non-competitive 2020:

What are the Cubs’ biggest areas of focus in improving a team that won 84 games and lost starter Cole Hamels, a handful of relievers and hitters Ben Zobrist and Nick Castellanos?

Epstein said he’s looking for a starting pitcher and expected to explore a free agent market that has more depth than usual – meaning a look at the second and third tiers of the market. He also said the bullpen is a priority, looking at both the trade and free agent markets. And among the non-pitchers, second base and, more importantly, center field are areas of to improve.

Wheeler’s signing for $118 million could push the payroll-conscious Cubs down the ladder among starters if, as expected, the five-year deal lifts the boats of the group just behind top free agent starters Gerrit Cole and Stephen Strasburg.

What does Russell’s departure mean for second base – and/or rookie Nico Hoerner?

Hoerner, who skipped Class AAA in for an emergency callup in September, handled himself well enough down the stretch to impress the brass and put himself firmly in play for the second base job heading into spring training – with the caveat that his status changes significantly depending on how he looks in the spring and what the Cubs might add to his position area this winter. Don’t forget David Bote among in-house candidates if he’s still around.

What about these trade talks? Who’s going? Who’s staying? Who’s off-limits?

Technically, nobody’s off-limits. That’s long-standing Cubs policy – and never more the case than this winter. But Rizzo’s probably not going anywhere, any leaks suggesting otherwise reading more like a motivator for an exceptional player who might yet have more ceiling. And All-Star shortstop Javy Baez has been talking to the team about an extension that could assure a lengthy stay in Chicago. Then there’s the Jason Heyward-Tyler Chatwood category of bad contracts that will take serious threading of needles to move.

Bryant, their best hitter, remains in play if only because an extension beyond 2021 appears such a long shot, but might be especially difficult to get top value in return this winter with third basemen Anthony Rendon and Josh Donaldson still available at free agent costs that won’t involve giving up any players.

Everybody else? Heads up.

Is it possible they won’t trade anybody?

Sure, anything’s possible. But don’t count on it. The Cubs in 2019 were one of only three teams to pay the luxury tax and didn’t get so much as a sniff at October for it. With the threshold rising only slightly to $208 million in 2020, they’re already operating with a roster bobbing at around $185 million for 11 players under contract and six more due arbitration raises. That doesn’t count anybody they might want to add, pre-arbitration salaries or the roughly $15 million all teams are assessed toward the threshold in player benefits.

Somebody has to go – or more than one somebody.