It's not 2014, but this offseason will be very important for the Cubs

Jed Hoyer has heard the comparisons, and he gets it.

After seeing what the Cubs did in the second half of the 2022 season, posting a 39-31 record in the second half, there’s growing optimism that this team is somewhat in a similar position heading into the offseason that it was at the end of 2014. Like that year’s club, the post-2022 Cubs have multiple players who look like stars in the making, they have some top prospects ready to come up as soon as next season and they have a lot of money they can spend in the offseason.

But does the Cubs’ president of baseball operations necessarily think the comparison between the 2022 and 2014 clubs is completely fair?

“I will say that I think it’s hard to compare those two things, because when you look back to where our best prospects were in 2014, a lot of those guys were in the major leagues at the end of that previous season, and then a lot of those guys had either dominated in Double-A or were already in Triple-A,” Hoyer, who was the Cubs’ general manager at that point in the last rebuild, said Monday during his hour-long, end-of-season press conference. “So, I do feel like at that point we were further along in terms of when those hitters were going to be in the in the big leagues. I don’t think it’s entirely fair to compare this to that. That said, from a pitching standpoint, I think we are further along now than we were at that time. I don’t think it’s fair to compare that.”

He’s certainly not wrong.

Whereas position-player prospects like Anthony Rizzo, Jorge Soler and Javier Báez had already put on the Cubs uniform and Kris Bryant and Kyle Schwarber would be up by mid-June the next season, a lot of the success in the system this time around comes from the improvements in the pitching infrastructure.

Justin Steele and Keegan Thompson had a lot of success this year, and Hayden Wesneski may have pitched himself into the rotation plans for next season. Brandon Hughes had an impressive rookie season, Javier Assad and Jeremiah Estrada moved quickly through the minors to make their debuts and prospects Jordan Wicks and Ben Brown may also be ready to pitch in the big leagues in 2023.

All told, it looks like the pitching depth may be there, and that’s far different than the position the Cubs were in eight years ago. But as far as similarities go, adding impact talent during the offseason is right at the top of the list.

Back then, a team in need of high-end starting pitching went out and signed Jon Lester to a six-year, $155 million deal. It didn’t matter that the Cubs weren’t seen as a contender just yet. That offseason was the right time to go after one of the better free agents on the market who fit a major need, and the Cubs brought him in.

“I will say that when we went out into the free agent market prior to 2015, it was really only for one significant player, which was Jon Lester,” Lester said. “A guy that we knew. We knew his makeup, we knew the toughness and the competitiveness and the maturity that he would bring.”

That’s pretty similar to the spot the Cubs find themselves in now. No, there probably aren’t any moves they can make that’ll turn them into World Series favorites in 2023, but this is the right time to identify the holes in the roster, and then go out and find the right players to fill them.

Hoyer talked the whole year about keeping an eye on the future, and he’s not interested in making moves he would deem are too short-sighted. However, that doesn’t mean moves made this winter can’t help the Cubs win next year and in the future, too.

“I think last season, we talked a lot about ‘intelligent spending,’ and I think we’ll certainly look to do that again,” Hoyer aid. “I want to build on the momentum that we created at the end of the year, but I know that we have some holes to fill, and we’ll be aggressive to try to fill those holes in the best way possible. I think we can definitely compete next year, and we also want to create something lasting and special. We’re always going to have to keep those two things in mind.”

Hoyer’s thinking about “intelligent spending” doesn’t rule anything out, but it also seems to mean he would only look to bring in free agents at the right price.

The front office would likely lean toward shorter-term contracts with higher average-annual values, similar to the ones they gave to Seiya Suzuki (five years, $85 million) and Marcus Stroman (three years, $71 million) last offseason. If a top-tier free agent wants a 10-year deal, it’s fair to think the Cubs won’t be involved in the bidding, but if you think they aren’t going to be active in free agency, you need only look at those two contracts from the first offseason of this rebuild to see that Hoyer is willing to spend money.

“We want to build something lasting and we want to build something that we’re proud of for a long time,” Hoyer said. “I think that you can get caught up in our game in transactions that feel really good in the short term and don’t make long-term sense. So, those are the ones we’ll avoid.”

But plenty of questions can also be asked: is this the crossroads offseason? Is this winter the time to get the players that could get this team in the postseason next year? Is this offseason that important in keeping this rebuild on track and perhaps even moving up the timeline?

“I wouldn’t label it anything other than, like, it’s a really important offseason to continue to build towards our goal,” Hoyer said.

Hoyer may not admit this offseason is more important than any other, but it does have that feeling. Signing Lester after 2014 — and, as Hoyer mentioned, making less-heralded moves to trade for Miguel Montero and Dexter Fowler — helped the club win 97 games and reach the National League Championship Series the next season for the first time in 12 years.

There are clearly holes on the current-day roster that can be filled not just with small moves, but with big free-agent splashes. Among them:

• The Cubs could certainly use a top-of-the-rotation starter
• MLB limiting defensive shifts starting next season will make athleticism up the middle even more important, and the Cubs could use an upgrade in that area
• The Cubs need to add more pop in the lineup

All of that isn’t going to be fixed with in-house options, so it’s up to Hoyer and company to identify the best (and the right) players on the market to do the job. He wants to build off the momentum the Cubs created during the second half of the season, but the first half showed that a lack of high-caliber players throughout the lineup plus a lack of depth will destroy any playoff hopes when the injury bug inevitably bites.

Hoyer said the organization “absolutely” wants to compete next year. Being aggressive and making the right moves this offseason will be incredibly important if the Cubs truly plan on meeting that goal.