The General Manager Meetings are over, and free agency officially began on Thursday. And with that, the most important offseason for the Cubs in years is finally underway.

At his end-of-season presser last month, president of baseball operations Jed Hoyer discussed his desire to build on some of the successes the Cubs had at the end of the season. But to do that, the entire front office needs to attack this winter head on.

From the rotation to the middle infield to the Rule 5 Draft, there’s still uncertainty regarding what this offseason will look like for the Cubs. For fans who don’t want to endure another year of losing, there are still plenty of problems that need solutions.

But just to narrow things down, here are five questions the Cubs need to answer this offseason:

1. Can they land a top-tier free-agent shortstop?

For the last two offseasons, the Cubs have been linked to the hottest names in the free-agent shortstop market. This time around, the rumors include Carlos Correa, Xander Bogaerts, Trea Turner and Dansby Swanson.

The Cubs have certainly kicked the tires on those players, but as far as getting a clearer picture on which one may end up donning a Cubs uniform… Well, we’re not all that much closer. The Cubs are in rumors involving Correa. Some have predicted Swanson moving to Chicago. Heck, there’s even speculation that the Cubs’ idea of “intelligent spending” may be hurting their chances of landing any one of them. This is what happens at the beginning of hot stove season, where teams are still just feeling things out and may even be waiting for the shoe to drop, so the rumors seem incredible wide-ranging.

But that still leaves onlookers guessing as to who will be manning short for the Cubs when Opening Day 2023 rolls around.

Hoyer has made it clear how impressed he is with what Nico Hoerner did this past season — “We have total confidence in Nico’s ability to play shortstop,” he said — but that doesn’t mean he thinks the Cubs are set at the position. With question marks surrounding the other internal options at second base, plus the need for premier up-the-middle defense thanks to the banning of the shift, adding a top-tier shortstop to the mix would certainly help shore things up.

There’s plenty of money for the Cubs to spend this offseason (Spotrac estimates them to be nearly $125 million under the luxury tax threshold in 2023), and adding a shortstop would be worth the investment. All that’s left for them to do now is seal the deal.

2. Which prospects are going to be protected?

The Rule 5 Draft isn’t until December, but the Cubs have only a few days left before they have to make a decision on which players they want to make sure stick around over the offseason.

Tuesday is the deadline for teams to add players to their 40-man rosters to protect them from the Rule 5 Draft, which is scheduled for Dec. 7. As of Friday afternoon, the Cubs had just 34 players on the 40-man following a flurry of roster moves:

Cubs moves today:

– Hendricks, Heuer, Heyward, Ortega and Roberts activated off 60-day IL

– Bote, Brault, Crook, Espinoza and Reyes cleared waivers and outrighted to Iowa

– Mills and Wieck activated off 60-day IL, cleared waivers and outrighted to Iowa

40-man at 36 players

— Ryan Herrera (@ryan_a_herrera) November 10, 2022

Another couple of Cubs moves today:

Esteban Quiroz and Jared Young both cleared waivers and have been outrighted to Triple-A Iowa.

Cubs' 40-man roster is down to 34.

— Ryan Herrera (@ryan_a_herrera) November 11, 2022

We know that Jason Heyward won’t be returning, as Hoyer has previously stated the Cubs will release him before the final year of his contract, so that number will soon be at 33. And from there, filling out the 40-man will come down to which minor leaguers the Cubs feel are important to protect.

Dozens of players in the system are eligible, though most won’t be taken thanks to the roster rules surrounding Rule 5 Draft picks. But at least three would almost certainly get selected if left unprotected: Brennen Davis, Kevin Alcantara and Ben Brown. Those are the three you can pretty much assume will be added to the 40-man in the coming days. But beyond them, are there any others the Cubs might be in danger of losing?

Just from MLB Pipeline’s top-30 Cubs prospects list alone, there are a number of names who will be under consideration. In addition to Davis (No. 2), Alcantara (No. 3) and Brown (No. 7), there’s Yohendrick Pinango (No. 18), Chase Strumpf (No. 25), Luis Devers (No. 26), Ryan Jensen (No. 28) and Kohl Franklin (No. 29), and then there are also non-top-30 prospects like Danis Correa and Darius Hill.

Outside of those top three, each come with questions that the Cubs will have to find answers to in the next few days:

• Are they in any danger of losing Pinango, who’s never played above High-A?
• Would a team want to keep Devers — who’s also never played past High-A ball but was the Cubs’ Minor League Pitcher of the Year — on the major league roster for all of 2023?
• Could other teams poach less-heralded prospects in Correa and Hill, who both finished the year at Triple-A and might soon be ready to take the next step?

The roster crunch has been discussed at length for most of the second half of the season, but now, the time to make those 40-man decisions is upon Hoyer and Co.

3. Are any extensions coming this winter?

We know Hoyer is looking to extend some of the players already on the roster. He said as much during his season-ending presser.

Of course, not extending any core players after the 2016 World Series was a huge criticism the Cubs faced last time around. It seems like Hoyer has flipped the script and is interested in keeping some of those guys around for the long haul, so the questions then become: who are the extension candidates, and when might they happen?

During that press conference, Hoyer was asked about Hoerner and Ian Happ, specifically. They’re both at different points in their career, with Hoerner just entering his first year of arbitration while Happ is entering his last, but both showed the team enough in 2022 to warrant extensions. Hoyer had said the front office had taken the “first steps,” but Happ clarified last week that those steps didn’t involve negotiating with the players just yet.

“I’m sure they’ve had the conversations internally. That’s probably what he was referring to. That’s the way that it works,” Happ said while on a Zoom call with the media to discuss his NL Gold Glove Award. “On the player’s side, it’s generally a lot later than a week after the season. Maybe there’ll be something down the road, but it’s their job to look at all possible outcomes and the way that that shapes their thinking for not only free agency and trades, but long-term internally.”

But something else came out of the GM Meetings that makes it seem like the Cubs want to hammer out extensions sooner rather than later.

“Don’t hold me to this, but I don’t really love negotiating in spring training,” Hoyer told reporters in Las Vegas this week. “The more I do it, the more I think it causes real tension. Guys want to start the season. I’ve watched many deals fall apart in spring training. I just don’t think it’s a great way to start the season. I think I’d like to push that up a little bit, and if we get it done, great.”

With an actually normal offseason upon them, the Cubs will have plenty of time to discuss extensions with some of their players. But whether they can get them “across the finish line” remains to be seen.

4. How will the rotation shake out?

At this point in the offseason, the Cubs have only two true locks for the rotation: Marcus Stroman and Justin Steele. They were Nos. 1 and 2 on the team with 25 and 24 starts in 2022, respectively, and as far as showing they can be relied on in 2023, they proved it. But everything else is still up in the air

Of course, the Cubs do have in-house options who could be a part of the group of starters

• Keegan Thompson at least has the floor of a viable multi-inning reliever but could still be a starter in the future
• Kyle Hendricks has been ineffective over the last two seasons and missed the second half of 2022 with a shoulder injury, but he has a proven track record as a starter and would certainly be worth a look if he begins spring training healthy
• Adrian Sampson and Javier Assad covered innings when they were called upon and could find themselves at the back end of the rotation
• Hayden Wesneski was impressive in September but probably shouldn’t be anointed a rotation spot right now

So, there are still question marks beyond Stroman and Steele. But with as much money as the Cubs have available, there are plenty of ways to take care of that in free agency. One player who’s been thrown around in connection with the North Siders is Kodai Senga, a free agent from Japan who could quickly slot into the rotation. As far as top-of-the-rotation starters go, Carlos Rodón, Justin Verlander and Jacob deGrom are options on the market, but rumors connecting them to the Cubs haven’t been very prevalent.

Still, there are plenty of names out there who could provide the “quality innings” that Hoyer is looking for. We should have a much clearer idea of what the Cubs’ rotation will look like by the time spring training gets underway.

5. Can they contend in 2023?

The Cubs went 39-31 in the second half of the 2022 season, a 90-win pace that would’ve had them in the thick of the playoff race had they been able to do that over the full 162. That stretch did give them some momentum heading into the offseason, though, and seeing what the expanded playoffs did for teams whose records wouldn’t have been good enough to make it in years past, there’s no reason the Cubs can’t capitalize by adding this winter and making a run at a playoff spot.

The 87-win Phillies just made it all the way to the World Series. The 89-win Padres upset the 111-win Dodgers in the NLDS. The Cardinals were upset in the Wild Card round, but their 93 wins were more than enough to win a weak NL Central.

There’s absolutely no reason the Cubs can’t push to be one of those teams. Their farm system continues to improve and should be churning out more big league talent in the near future. The pitching infrastructure could soon get to a point where the majority of the Cubs’ pitching staff is homegrown arms.

Getting more good players through free agency likely won’t make them World Series contenders next season, but playoff contenders? Absolutely.

This is something of a crossroads winter for the Cubs, probably their most important winter since 2014. There are plenty of avenues for them to take now that the offseason is officially underway, and if they do it the right way, there’s certainly reason to believe they can be right back in the postseason in 2023.