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When will Shohei Ohtani make a decision? 3 questions facing the Chicago Cubs ahead of the winter meetings.

Shohei Ohtani just had arguably the greatest three-season run in the history of the sport, and it netted him two unanimous AL MVP awards and a runner-up finish.

Two months ago, during the final week of the season after the Chicago Cubs’ tenuous hold on a playoff spot had slipped away, president of baseball operations Jed Hoyer looked across the field in Atlanta at the standard they were trying to reach.

The Braves, winners of six consecutive division titles and a World Series championship in that span, have become an offensive force and are yearly one of the teams to beat.

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“Whenever I see a great team like this, I actually look at it as inspirational — that’s the standard,” Hoyer said. “And to get where you want to go, that’s where you have to get.”

Reaching that level will take more than one offseason and will require the Cubs to return to the postseason for the first time in a full season since 2018. Hoyer and the Cubs have multiple paths to building a playoff roster in the next two months, with Shohei Ohtani representing the marquee prize.

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Free-agent signings and trades should pick up at the Gaylord Opryland Resort in Nashville, Tenn., the site of Major League Baseball’s annual winter meetings. Ahead of the four-day event that starts Monday, here is a look at three questions the Cubs face this offseason.

1. When will Shohei Ohtani make his decision?

Angels pitcher/designated hitter Shohei Ohtani at the team's spring training complex on Feb. 21, 2023, in Tempe, Ariz.

Ohtani and his representation have kept his free-agent process extremely quiet publicly, with limited insight into any priorities in choosing his next team or the time frame to make his decision.

Ohtani will have a hold on baseball until his destination is announced, and with that, any teams fully involved in attempting to sign the superstar inherently have to put other roster-building decisions on hold.

Cubs fans have embraced the dream over the last month of Ohtani becoming the star attraction at Wrigley Field in 2024 and beyond. Hoyer’s stealth pursuit and hiring of manager Craig Counsell last month provided a reminder of his shrewd maneuvering and how he can pull off these types of moves.

If Ohtani commits to a team by the end of the winter meetings, the Cubs are among the most notable clubs whose offseason direction gains a lot of clarity. There are avenues beyond Ohtani — though none singularly powerful on or off the field — for the Cubs to build a winning team, but it starts with him.

2. Is this the offseason the Cubs leverage their farm system to add through trades?

Matt Mervis drives in a run for the Cubs with a single against the Marlins on May 4, 2023, at Wrigley Field.

The Cubs boast one of the top minor-league systems, in both quality of depth and high-end prospect talent. What they have been able to do through development, scouting and drafting the last three years after committing to what became a short rebuild in 2021 has set them up to use that talent pool to acquire proven big-leaguers.

The Cubs, importantly, wouldn’t need to deplete from their top prospect group to bring in a major-league-quality player or two, putting them in an advantageous position. Beyond the prospects who have not reached the majors, the Cubs could look to move younger big-league-caliber players.

Christopher Morel remains a potential key trade piece because of his limited roster fit and the star upside the 24-year-old has shown as an electric utility player.

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But unless Morel and the Cubs are able to make either center field, first base or third base work defensively as the spots where the most non-designated-hitter playing time is available, Morel’s greatest help to the Cubs might be in a trade that addresses a positional need.

Lefty slugger Matt Mervis represents another intriguing on-the-cusp player who struggled in limited action (99 plate appearances) during his debut season. Bottom line: The Cubs will have plenty of options to offer in a strong trade package for an impact player.

3. How will the Cubs bolster their pitching staff and the middle of the order?

The Rays' Tyler Glasnow pitches against the Red Sox at Tropicana Field on Sept. 6, 2023.

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Even if the Cubs land Ohtani, their efforts to build a complete team wouldn’t be done, though it would lessen the pressure to land a middle-of-the-order bat.

With Cody Bellinger’s impending departure through free agency, the Cubs already need to replace his slugging production should he end up elsewhere while finding another power hitter.

Former Philadelphia Phillies first baseman Rhys Hoskins makes a ton of sense on either a one-year pillow contract or shorter multiyear contract because of his power and patient approach at the plate. A trade also could address either corner infield position.

Center field presents an option to platoon if the organization is confident Pete Crow-Armstrong will take the next step in his development at the big-league level in 2024 after struggling as a September call-up.

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The Cubs desperately need more swing-and-miss specialists on their pitching staff.

Rays right-hander Tyler Glasnow, who is owed $25 million in the final year of his deal, certainly offers that. He owns a 33.5% strikeout rate since 2018; however, he has been limited to 60 starts the last five years because of injuries. The Cubs will look to add whiffs and experience to an experienced bullpen that wore down by the end of their disastrous September collapse.

The Cubs sit in a great position. They possess financial flexibility to add top players without needing to find that solely through free agency. By the time everything shakes out, they could help define the MLB offseason.


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