Can the Chicago Cubs lock down a top free-agent shortstop? 3 questions as the winter meetings begin.

SAN DIEGO — A quiet start to the offseason sets up an important winter meetings for the Chicago Cubs.

President of baseball operations Jed Hoyer previously vowed to be aggressive in upgrading a 74-88 roster. But the Cubs’ moves will ultimately determine whether the organization flexes its financial flexibility. As major-league teams’ personnel arrived in San Diego ahead of the offseason’s marquee gathering that runs through Wednesday, the Cubs have an opportunity to take advantage of a division that appears devoid of much competition.

The Cubs are expected to increase their spending from their 2022 payroll of $167,068,737, per Spotrac, which put them 13th in the league. They have a ways to go to surpass that level with $124,310,000 currently on the books for 2023, according to Cot’s Contracts; that includes $22 million owed to Jason Heyward, who was released last month.

Those payroll figures leave the Cubs plenty of room to acquire the type of impactful talent they need to build off last offseason’s main additions of Seiya Suzuki and Marcus Stroman.

But will the Cubs be serious spenders? It’s one question, among others, that looms this week at the winter meetings.

The most obvious way the Cubs can infuse more talent is through signing one of the four standout free agent shortstops.

To what extent the Cubs are willing to commit future financial resources will likely guide who they most aggressively pursue among Carlos Correa, Trea Turner, Xander Bogaerts and Dansby Swanson. Correa, Turner and Bogaerts offer the most consistent offensive track record and star power, while Swanson’s defense and potentially least costly option makes him an attractive.

Bogaerts, 30, and Swanson, 28, have emerged as the focus of the Cubs’ interest. Bogaerts’ offensive production — 133 OPS+ over the last five seasons in Boston — would provide an immediate boost to the lineup. Swanson presents a bigger defensive upgrade at the position; pairing him with Nico Hoerner at second base could create a strong pairing up the middle. Although Swanson has posted an OPS+ over 100 only twice in his last six seasons, the Cubs believe they would be able to tap into more production from his bat.

[ [Don’t miss] Column: It’s time for the Cubs and White Sox to make some noise at the winter meetings — especially for their fans ]

The Cubs can’t afford to whiff on acquiring a dynamic star hitter. They have so many holes to fill that addressing all of the weaknesses will take multiple offseasons. The process began last year, and the front office still has plenty of work ahead.

The shortstop free-agent class presents a test for whether the Cubs are willing to spend big bucks in a market that has already shown a pricey cost on the starting pitching side.

Tapping into external options remains an avenue for the Cubs at center field.

Injuries to top center field prospects Brennen Davis (stress reaction in his back) and Alexander Canario (surgery on left ankle and left shoulder) created uncertainty as to how much the Cubs can realistically expect to rely on them next year. Canario faces a lengthy rehab process. Davis’ lingering back problems are concerning.

Former 2019 National League MVP Cody Bellinger is an intriguing reclamation project and short-term option. Bellinger doesn’t turn 28 until July and still provides stellar defense despite posting a .193/.256/.355 slash line and 64 OPS+ in 900 plate appearances over the last two years. Whichever teams signs Bellinger must believe he is willing and able to implement the swing and approach changes necessary to get him back on track.

[ [Don’t miss] What’s the current state of Chicago baseball? 4 lifelong Cubs and White Sox fans weigh in. ]

Improving in center field was a noted focus for Hoyer and the Cubs after the season.

Pete Crow-Armstrong looks like the real deal after starring at High-A South Bend. But the previous two months also served as a reminder as to how quickly long-term plans can go awry if injuries afflict top prospects. The Cubs ideally do not want to block Crow-Armstrong, but prospects are just prospects until they reach the majors and produce.

Chicago Tribune Sports

Weekdays

A daily sports newsletter delivered to your inbox for your morning commute.

If the organization extends Ian Happ, the Cubs could have the corner outfield spots locked in for the next few years, leaving a balancing act for how the acquire an outside upgrade in center field while maintaining some outfield flexibility.

The starting pitching market has ramped up in the past week, both on a bigger and smaller scale.

Jacob deGrom became the first top-tier starter to sign after inking a five-year, $185 million contract with the Texas Rangers. Zach Eflin (three years, $40 million with Tampa Bay Rays), Matthew Boyd (one year, $10 million with Detroit Tigers), Mike Clevinger (one year, $12 million with White Sox) and Kyle Gibson (one-year deal to Baltimore Orioles) all found new homes.

The Cubs need to supplement their rotation. Should they opt to stay away from the high-end costs that Carlos Rodón and Justin Verlander, in particular, are expected to command, the market is poised to still be robust with options to add depth and upside. That might not sound exciting for Cubs fans supporting a team that can use a top starter to pair with Stroman.

[ [Don’t miss] Chicago Cubs hired a baseball scientist last month. Meet Mike Sonne — and see what he hopes to do for the team’s on-field performance. ]

The organization must find reliable pitchers, both for the rotation and bullpen, that go beyond potentially trade deadline flip pieces.

Starting pitcher injuries decimated the Cubs early in the 2022 season. They need to avoid that scenario in 2023. It will require the Cubs to engage in a free-agent market that to this point hasn’t exactly been cheap for the middle- to lower-tier choices.

With their payroll room, that should not be a hindrance to bolstering the pitching staff.