With the way the Cubs tore down their roster and mostly steered clear of long-term, big-money contracts over the last few years, it’s no surprise some fans remain skeptical that the front office will actually go out and pony up the type of deal necessary to reel in a free-agent shortstop this winter.

President of baseball operations Jed Hoyer isn’t one to show his hand, but the prevailing wisdom is that the Cubs aren’t keen on giving out contracts that cover years approaching double digits, especially for position players who have either reached or are nearing 30 years old. It all ties back to Hoyer’s message about “intelligent spending” (i.e. spending in a way that won’t sacrifice future financial flexibility).

“To me, ‘intelligent spending’ involves making decisions that make sense for the 2023 season, but also aren’t going to hinder what we’re trying to build,” Hoyer said during his end-of-season press conference last month. “The nature of baseball contracts is challenging that way, because we’ve all seen contracts of certain lengths that can really bog a team down. It’s easy to talk about the player you’re acquiring, but if that contract ends up hindering the ultimate goal here — which is to build something special and sustainable and lasting — then it wasn’t a good transaction.”

The most recent and obvious example of that kind of contract on the North Side is Jason Heyward’s eight-year, $184 million deal. He was just 26 at the time, had just come off a career-high 5.6 fWAR season in St. Louis and was a Gold Glove-caliber right fielder barely in his prime, but he ultimately didn’t live up to the deal during his seven seasons with the Cubs and was released from the last year of his contract (worth $22 million in 2023) on Monday.

That alone would make anyone wary of giving out similar deals to future free agents. However, not every player is the same and not every contract will turn out like Heyward’s. One bad deal shouldn’t stop the Cubs from wanting to invest money into star players, and in fact, the two other big contracts the Cubs handed out during the last competitive window are examples of why they should do just that.

Prior to the 2015 season, the Cubs went out and signed Jon Lester to a six-year, $155 million deal. Three years later, they added Yu Darvish on a six-year, $126 million pact. By the end of it, Lester’s deal was the best free-agent signing in franchise history, while Darvish struggled through a bumpy and injury-plagued first year and a half before finding his ace-like stride and ultimately netting the Cubs a nice package of prospects when he was traded to the Padres after 2020.

Of course, both Lester and Darvish were pitchers, so Heyward is the only recent example of what could happen when the Cubs give a contract of that size to a position player. Still, those star players are the ones who play a huge hand in helping teams win — and Hoyer knows that.

“I think it’s a question that comes down to timing,” he said. “You want to make sure that you add those players at the right time to the organization, and we have to make those decisions. There’s no question that those caliber players can certainly swing a playoff series or make the difference in a couple of games to make the playoffs or not make the playoffs, but you have to make sure you sign those players at the right time.”

As far as timing goes, there couldn’t be a better time for the Cubs to be players in the shortstop market. The “Big Four” free-agents shortstops — Carlos Correa, 28; Trea Turner, 29; Xander Bogaerts, 30; and Dansby Swanson, 28 — are all former All-Stars. They’re elite-level shortstops.

The Cubs have a need up the middle with only Nico Hoerner being a plus-defender at both shortstop and second base, and with rules against defensive shifts being implemented next season, bringing in another proven middle infielder is a no-brainer. Add in the fact that the Cubs are looking for more power in their lineup, and it’s evident that any of Correa, Turner, Bogaerts or Swanson would check multiple boxes for the team this offseason.

Hoyer has maintained that he has the utmost confidence in Hoerner to play the position, but even he has to admit that adding another shortstop to the mix would only help the team (assuming health and performance live up to the deal).

“I look at the shortstop situation kind of the way you look at the draft, which is, if you drafted a shortstop every year you’d be in good shape,” Hoyer told reporters at the GM Meetings in Las Vegas last week. “The best defenders usually play shortstop, the best athletes often play shortstop, those are guys you can move around.”

At this point, it has become obvious that the Cubs would like to bring one of those shortstops aboard. The question is: are they willing to spend what’s needed to do so?

Nobody knows for sure what it’ll take to land one of these players, but here are some predictions from across the baseball media landscape:

• MLB Trade Rumors: Correa (9 years, $288 million); Turner (8 years, $268 million); Bogaerts (7 years, $189 million); Swanson (7 years, $154 million)
• The Athletic: Correa (8 years, $260 million); Turner (8 years, $296 million); Bogaerts (7 years, $175 million); Swanson (7 years, $168 million)
• ESPN: Correa (8 years, $265 million); Turner (8 years, $272 million); Bogaerts (6 years, $168 million); Swanson (6 years, $150 million)

Clearly, not everyone really agrees. But if the average of these numbers provides a good indication, for Correa, it’ll take 8-9 years and roughly $271 million; for Turner, eight years and roughly $278 million; for Bogaerts, 6-7 years and roughly $177 million; and for Swanson, 6-7 years and roughly $157 million.

For at least Correa and Turner, it’ll take a franchise-record deal (in terms of dollars) to bring them aboard, and for all four, it’ll take a lot of money and a long-term commitment to convince them to join the Cubs. That doesn’t necessarily match up to what “intelligent spending” has meant for this team recently.

“Intelligent spending” has meant signing Seiya Suzuki to a five-year, $85 million deal (plus a $14.625 million posting fee) to come over from Japan. It has meant signing Marcus Stroman to a three-year, $71 million contract to move from New York to Chicago. The assumption is that the Cubs aren’t worried about the money (especially since they have plenty of room under the $233 million luxury tax threshold next season) as much as they are the years. But while they’d likely prefer deals with higher AAVs and shorter commitments, these shortstops may be more interested in long-term security than how much they’ll make in a given year. So, it might take the two sides meeting somewhere in the middle or even the Cubs going higher than they want to to land one of them.

And should the Cubs be willing to do that? Absolutely they should.

Elite shortstops in this age group don’t hit the market at this rate, and this comes when rule changes will make high-level middle infielders even more valuable. The Cubs have such an obvious need to sign one of these shortstops that not doing so would make it that much harder to call this offseason a success.

Now, it would be an easier pill to swallow if the Cubs did make good enough offers, but the four decided to sign elsewhere regardless. You can at least live with that. But if it comes down to Hoyer and company not being willing to meet a reasonable asking price just because it’s a bit higher than they’re comfortable going, then that would be an indictment on the front office’s commitment to improving the roster and competing in 2023.