With the most important season of his big league career in front of him, Willson Contreras continually faces questions about his future. Those questions hardly have to do with the game he plays for a living, though, as much as they revolve around if the Cubs will continue to pay him to play that game for them.

“Do you think this is going to be your last year?”

“Have you had any talks about a contract extension?”

“Would you be open to talks?”

“Do you need to see the team’s plan for the next few years before committing to an extension?”

Contreras, at peace despite the uncertainty surrounding his future in Chicago, responds to most of those questions with a “whatever happens, happens” type of attitude.

“I’m still here. This is my team,” Contreras said outside of the Cubs spring training complex in Mesa, Arizona, on March 13. “I’m still here, and even though this is the last year (of his contract), whatever is going to happen between the middle of the year or the end, I’m happy with it.”

Fast forward 10 days, and things were still the same. Standing in front of his locker on Wednesday, Contreras echoed those comments he made at the beginning of spring training:

“I love my team. I love the Cubs. I love my teammates,” Contreras told reporters. “My main focus right now is to play baseball. It’s to stay healthy, stay on the field. That’s the only thing that I can control.”

Contreras will be going into the season without a set idea of how much he’ll be making to play for Chicago in 2022. As MLB.com’s Mark Feinsand reported on Tuesday, when the two sides exchanged proposed salary figures, they were about $1.25 million apart. Now, an arbitration hearing will be held during the season, where a panel will choose between Contreras’ proposed $10.25 million salary and the Cubs’ proposed $9 million salary.

A hearing will certainly take place, and eventually, the two sides will figure out how much Chicago will pay Contreras for the upcoming season. The bigger issue, though, is where Contreras is playing baseball beyond this year.

It’s the lack of a contract extension from the Cubs that’s making this upcoming season an uneasy one, because despite Contreras seemingly being content to let things play out, Chicago has been through this process before.

And it ain’t too pretty.

What we’ve seen in the ‘past’

As the Cubs broke up the core of their 2016 World Series championship team leading up to the 2021 trade deadline, reports said there was at least some communication between Chicago and those players. How deep that communication went is inconsequential, because regardless of what talks were had, they ultimately led to zero contract extensions.

Kris Bryant? The 2016 National League MVP and 2015 NL Rookie of the Year went into the 2021 season without an extension and was traded to the Giants on July 30. Last Friday, Bryant inked a seven-year, $182 million deal with the Rockies.

Anthony Rizzo? He also went through last season without an extension (or at least a second one after his first in 2013) after reportedly turning down a five-year, $70 million offer from the Cubs. He was traded to the Yankees on July 29 and re-upped with the Bronx Bombers on March 17 on a two-year, $32 million pact.

Javier Báez? Extension talks were halted because of the COVID-19 pandemic in March 2020, he began last season on the last year of his contract and he was dealt to the Mets on the same day as Bryant. He avoided the lockout uncertainty by signing a six-year, $140 million contract with the Tigers on Dec. 1.

And that’s not to mention Kyle Schwarber, who didn’t even make it to the regular season after he was non-tendered in December 2020. He signed a one-year, $10 million deal with the Nationals last January, was traded to the Red Sox on July 29 and eventually signed a four-year, $79 million deal with the Phillies on Sunday.

Again, reports said at least some communication was being had between the parties before those players became former Cubs at the deadline. Nowadays, it’s a lack of communication that might be pushing one of the last remaining members of that championship team out of Chicago.

At the start of camp, Contreras said he hadn’t been approached by the team about any contract extensions. President of baseball operations Jed Hoyer rebuffed that idea, stating that the two sides had had extension talks in the past, but the 99-day lockout and the scramble to fill out the roster during the abbreviated offseason had pushed extension talks a little lower on the list of priorities.

It began to feel like last year’s post-trade deadline fallout, when Hoyer seemed to pass the blame on the lack of extensions to the players (though he did walk that back the next day), followed by pushback from both Rizzo and Bryant.

Fortunately for both sides in this round of negotiations, the player at least understands why his extension has been pushed to the side for the time being.

“I think it was just too short of time, that’s all I can say,” Contreras told reporters on Wednesday. “I mean, the lockout, we know that was super long, and, basically, we just got here. They had no time to negotiate. They are adding players. They still are. I’m really glad with the job they’re doing. Like I said, they know what to do (that’s) best for the team. That’s all I can say.”

While putting extension talks on the back burner gave Hoyer and Co. more time to focus on quickly filling out the roster, it may also be what ends up causing another World Series Cub to leave the North Side.

Contreras has already said that he doesn’t want to have extension talks during the season. He wants to either get one done before the season — which seems unlikely given that Opening Day is in exactly two weeks — or he wants to reopen talks once it ends. In between, he wants to just focus on baseball.

A contract extension coming after the season just doesn’t seem likely at this point, but let’s say talks really heat up over the next 14 days or Contreras allows them to continue into the year.

Here’s what an extension might look like for a soon to be 30-year-old catcher who’s also a two-time NL All-Star with a championship ring:

Imagining a Contreras contract

There are only two realistic possibilities between the Cubs and Contreras at this point. One, they don’t agree to a contract extension and explore trading him by the July deadline. Or two, they get an extension done and continue building around Contreras.

If the Cubs go the path of an extension, they could look across town for a template. The years and dollars that Yasmani Grandal got from the White Sox in 2019 would make a lot of sense for Contreras, too. The South Siders signed Grandal for four years and $73 million prior to the 2020 season. At the time, Grandal was in many ways a very similar catcher to Contreras.

Grandal was a year older than Contreras is now, but he had a similar track record. All-Star appearances in 2015 and 2019 and offensive numbers in line with what Contreras has put up since debuting in 2016 make Grandal a good comp. Contreras will turn 30 in mid-May, and his durability makes a four-year or even a five-year deal reasonable.

As things stand now, the Cubs will be well below the 2022 competitive balance tax threshold. According to Spotrac’s estimations, they will have close to $60 million in CBT cap space. In the near future, their payroll will get even slimmer. Ian Happ will be in his final year of arbitration in 2023, and next season is the last of Jason Heyward and Kyle Hendricks’ contracts (Hendricks has a vesting option for 2024).

If the Cubs extend Contreras with a deal similar to Grandal’s, he should be productive for the bulk of his new contract. It might be wise to build in a club option near the end of an extension, but if the Cubs intend to be competitive again in the near future, Contreras should be a part of that.

However, the first few months of the season might end up dictating the direction things take. A sub-.500 Cubs team probably starts looking at trade options come July, and Contreras would be very valuable on the mid-season market.

Given how the conversations appear to have gone and the compressed timetable of the offseason brought by the lockout, a contract extension before Opening Day does not look likely at this point. Chicago could choose to play out the season with Contreras and hope to extend him next winter, but that would open up the potential for Contreras to end up going elsewhere in free agency, leaving the Cubs empty-handed.

It appears much more likely that Cubs fans will have to deal with the trade of another beloved member of the 2016 team. Along with Hendricks and Heyward, Contreras is the last piece of that core. Saying goodbye to Rizzo, Báez and Bryant was difficult for Cubs fans last summer, and that wound is still fresh. The Wrigley faithful might have to brace for that wound to get a little deeper.

Bye-bye Willy?

If we go with the idea that this is indeed Contreras’ last season, it’s much more likely that the Cubs get what they can for him before the deadline.

Would Chicago risk letting him hit the market in November and possibly lose him for nothing? As we saw last year, that’s probably not how this front office will operate around the trade deadline if the Cubs aren’t in a position to be buyers.

Chicago would certainly welcome Contreras back on an extension that makes sense. He’s the heart of the team, the emotional player who was happy taking on the leadership role left behind by his former teammates. But with the way this offseason has gone, how likely is it that Contreras’ situation will have a different outcome than theirs?

The Cubs already announced on Wednesday that they had agreed to contracts with 28 of their 40-man players with 0-3 years of major league service. The same day that the team and Contreras exchanged figures, Chicago and Happ avoided arbitration by coming to terms on a one-year, $6.85 million contract. Right now, every player on the roster — including the other remaining World Series winners, Hendricks and Heyward — is under contract for 2022. Everyone, that is, except for Contreras.

That’s just another example of what makes this situation puzzling. Arguably the most important player on the roster is the only one who will go into the regular season not knowing what he’ll be getting paid for his services. And on top of that, he likely still won’t know what’s in his future beyond 2022.

As he’s made clear time and time again since the beginning of Cubs camp, Contreras will be at peace with whatever happens.

What about if Chicago trades him mid-season?

“Every time that I see trade rumors and I read them, I’m proud of myself,” Contreras said during that first interview on March 13. “That means that I’m doing good things that the other teams might need or the other team sees good in myself.”

And what if the Cubs let him test the market?

“It would be fun,” Contreras said in the same interview. “I think it would be like a dream coming true, especially coming from the bottom of the organization. Because I started as a third baseman, coming all the way through the minor leagues, converted as a catcher and then earned my spot as a Chicago Cubs catcher, and it would be fun to have that experience.”

Despite both sides publicly stating they want to stay together, there’s a very real possibility Chicago parts ways with another core member of one of the most successful runs in Cubs history.

Contreras isn’t going to let that distract him. Since the start of spring training, he’s been more vocal, been running all the drills, played in three spring games and just generally seems to be happy around his team.

He’s said those things consistently, and now he’s showing that on the field. Whatever happens moving forward, it’s clear Contreras is content to let the chips fall how they may.