Can the Cubs still have a successful offseason?

As the Major League Baseball offseason continues moving forward, the Cubs’ offseason continues moving forward at a pace that’s made Cubs fans anxious for something to happen.

They’re one of the few teams to still have not spent a dollar on adding any free agents to their major league roster. While it’s true that only a few of the top names on the market — either free agents or trade candidates — are officially off the board, most of the other big league teams have at least added players to fill out the margins of their rosters. Meanwhile, the Cubs have been silent.

Could they have signed someone by now, like a bullpen piece to provide a boost to the relief corps? The Cubs haven’t operated as a group that puts all of its eggs into one basket — especially when that involved someone like Shohei Ohtani, who was going to have a lot of suitors and thus likely needed a bit more of their focus in their recruitment — so it’s curious that no deals, even on the minor-move side, have materialized.

Cubs president of operations Jed Hoyer made it clear at the Winter Meetings earlier this month that he wasn’t operating under the mindset that he has to “win the offseason.” With Ohtani (Dodgers) off the board, Juan Soto (Yankees) and Tyler Glasnow (Dodgers) no longer on the trade market and Yoshinobu Yamamoto likely headed elsewhere, winning the offseason doesn’t seem like a possibility anymore, anyway. But Hoyer still has work to do to make this a successful offseason for the Cubs.

“You just don’t know where the best deals are going to come from,” Hoyer said. “Certainly, there’s immensely talented players on the market, but I think if you go in thinking it’s one of those guys or bust, you can make some really bad, long-term decisions. Trying to win the offseason is not a good idea. We’ll just try to make the best decisions we can, and I think if we do that, we’ll be in a good position.”

Now, where exactly can those types of impact deals still come from?

The obvious name to monitor is Cody Bellinger. Hoyer pointed to Bellinger’s one-year deal with the Cubs a year ago as one that “wasn’t exactly a move that people were lauding tremendously last year,” but it turned into perhaps the best value deal considering Bellinger’s 10th-place finish in National League MVP voting.

This time around, however, the Cubs of course won’t be finding a value deal with Bellinger. After his performance in 2023 on his “pillow contract,” the 28-year-old is looking to cash in, and reports continue to say his side is looking for a deal worth over $200 million. And with Scott Boras as his agent, there’s a very good chance Bellinger’s free agency stretches past the holidays — and potentially even closer to when players begin to report to spring training in February.

It could take a while, but for the Cubs to have a successful offseason, bringing back Bellinger would certainly be a good place to start.

If there is a value deal that could be had at a position of need, Rhys Hoskins is an option.

Also represented by Boras and coming off a torn ACL that cost him the 2023 season, Hoskins may be another chance to get an impact player on a short-term deal. Boras hasn’t ruled out another ruled out another “pillow contract,” and the Cubs would definitely not be opposed. And considering their first-base situation, even a two-year contract could make sense, too. MLB Network’s Jon Morosi, speaking on the CHGO Cubs Podcast during the Winter Meetings, was a supporter of a multi-year deal between the two sides.

“He is a reliable player, he’s got a good track record, impeccable reputation. He would blend really well I think with [Cubs culture-setters like] [Nico] Hoerner and Dansby [Swanson],” Morosi said. “If I were the Cubs, I would really want to get a guarantee without an opt out of more than a year, because if you’re going to spend that money, it’s because you believe in him. I would not try to halfway this thing. Go into it and say, ‘I believe that you’re going to be healthy. I’m going to pay you like I know you’re going to be healthy. I’ve seen your track record.’ … I’m a believer that he’s going to be just fine, and I think he’d be a tremendous fit for the Cubs.”

Whether that actually comes to fruition is anyone’s guess. The longer Hoskins stays on the market, the longer other team’s have to negotiate with his reps. If the Cubs want him, it’s up to them to go and get him.

While either Bellinger or Hoskins (or both, really) would fill obvious holes on the position-player side, there aren’t many realistic options to do so on the pitching side for the Cubs.

As previously mentioned, the chances Yamamoto comes to Chicago or slim to none. There’s been no mention of talks between the Cubs and reigning NL Cy Young Blake Snell. Jordan Montgomery and Shoto Imanaga are possibilities but far from guarantees.

What about on the trade market? There’s Dylan Cease (White Sox) and Corbin Burnes (Brewers), starters who’d be great additions to the top of the rotation. But the Cubs have not really been linked to those two outside of speculation about their availability and fit.

The Cubs have been connected to Cleveland’s Shane Bieber, and considering the Guardians’ situation, there have been rumors they could even be interested in acquiring someone like Emmanuel Clase or Josh Naylor in a bigger deal. Those would be improvements to the roster, for sure.

The anxiousness emanating from the fan base is completely understandable.

Sure, Swanson’s official signing was still a day away at this time in 2022, but by then they’d also already brought in Bellinger, Jameson Taillon and Brad Boxberger. So, after committing over $265 million to major league free agents a year ago at this time, concern that the Cubs are still sitting at $0 committed to free agents this deep into the offseason makes sense.

But just because they haven’t signed or traded for some of these names doesn’t mean they won’t. Free agency in baseball is a different beast, and sometimes, the biggest names on the market make teams wait. That’s just how it works.

So no, the Cubs aren’t going to “win” this offseason, but there are a number of ways for them to still have a successful winter and put an improved ballclub on the field in 2024.