What's in store for Cubs at Winter Meetings?

CHICAGO – While discussing the state of the Cubs' roster last month, president of baseball operations Jed Hoyer described what he called a "holy grail" position for a ballclub. That is when there are only a few targeted needs in the offseason, with younger homegrown players locking down other positions.

This winter, the Cubs are still in a transitional phase -- the bulk of its perceived impact prospect pool may not be ready in 2023 -- but they appear to be getting closer to playoff readiness. Hoyer's front office has spending power to try to close that gap even more, but there are multiple needs up and down the Major League group.

"It's a good feeling to have flexibility," Hoyer said at the GM Meetings last month in Las Vegas. "But, we also have a lot of holes to fill and, hopefully, over time, a lot of those get filled internally."

Next week, Hoyer and his team will arrive in San Diego for the Winter Meetings, where this quiet offseason is expected to gain steam. Will the Cubs get closer to landing one of the Big Four shortstops (Carlos Correa, Trea Turner, Xander Bogaerts or Dansby Swanson)? Will Chicago find an impact rotation arm (Kodai Senga, perhaps)?

Here is a breakdown of where things stand for the Cubs ahead of the Winter Meetings:

Key Events

• Sunday, Dec. 4: HOF Contemporary Era ballot results released (Albert Belle, Barry Bonds, Roger Clemens, Don Mattingly, Fred McGriff, Dale Murphy, Rafael Palmeiro, Curt Schilling)

• Monday, Dec. 5: All-MLB Team announced

• Tuesday, Dec. 6: Inaugural Draft Lottery, AL/NL Relievers of Year announced

• Wednesday, Dec. 7: Rule 5 Draft

Club Needs

The Cubs’ moves to date this winter have been around the edges of the roster, leaving the main areas of need still unaddressed. Chicago is in the market for an impact offensive player (signing one of the big-ticket shortstops is one avenue), rotation help, bullpen depth, a first baseman, a center fielder and a backup catcher. Is that all? There’s still a lot of work to be done for the North Siders.

Potential Trade Candidates

Left fielder Ian Happ – an All-Star and Gold Glove winner last season – had his name in rumors at the Trade Deadline last summer. Given that Happ is entering the final year of his contract, he might still be a target for teams. That said, Chicago may also use this offseason to try to extend Happ, who is growing into a leadership role for a roster undergoing a youth movement.

Beyond Happ, there are not many obvious trade candidates on the MLB roster. Veteran Kyle Hendricks has one year left on his deal (plus an option for ’24), but he is coming off an injury-marred campaign. Underneath the MLB group, the Cubs have a more robust farm system to pull from in trade talks, but Chicago is also still balancing competing now with building for the future.

Prospects to Know

For most of their free-agent talks, the Cubs will likely focus on shorter-term contracts, especially given the prospects who are coming soon. Outfielder Brennen Davis (No. 2 on Pipeline's Top 30 Cubs list) is coming off a year filled with health setbacks, but could reach the big leagues next season. The Cubs are looking for help at first base, but they're balancing that with the expected arrival of slugging prospect Matt Mervis (No. 21). There are also a host of pitching prospects who could impact the rotation and/or bullpen in 2023.

Rule 5 Draft

Given the Cubs’ long list of needs, this could be a year to roll the dice on a Rule 5 selection (perhaps in the bullpen) to scout up close in Spring Training with the possibility of cracking the roster. Chicago did not protect a long list of players, including four from its Top 30 list: OF Yohendrick Pinango (No. 18), INF Chase Strumpf (No. 25), RHP Luis Devers (No. 26) and RHP Kohl Franklin (No. 29).

Burning Question

Are the Cubs willing to spend big to land a superstar shortstop?

That is the question on the collective minds of Cubs fans right now. The North Siders are not one piece away from being a legitimate contender, but the club looks to be on the rise with prospect talent climbing up the system. The division is winnable, the team has both spending power and flexibility and there are four big-name free-agent shortstops available. Landing one might require stepping outside a comfort zone (both in cost and contract length), but star power is something the Cubs need as they try to regain their footing for a run at an October berth.