The Chicago Cubs entered the 2021 season with a feeling that this was a last hurrah. The team was coming off a disappointing sweep in the playoffs against the Miami Marlins with plenty of questions surrounding the core that won the World Series back in 2016.

Only a few days into June and the Cubs find themselves near first place despite the relatively low expectations heading into the season. 

“We did a preview at NBC Sports Chicago in late March and I pinned their record at 85-77,” DePaul alum and Cubs writer at NBC Sports Chicago Tim Stebbins said. “That obviously didn’t look so good in April. It started off not so well but they’ve definitely turned it around. Entering the season, the expectation for the NL Central was that it was the most wide open, in part, because there was no powerhouse team.”

Stebbins wasn’t the only one who had the Cubs being around mid-80s in wins. PECOTA, which annually releases their projections before the start of the season, also had the team finishing second with 85 wins and four games behind the Milwaukee Brewers.

However, the team’s early success has also raised some questions with regards to not only the present but the future as well.

The Cubs’ core of Anthony Rizzo, Kris Bryant and Javier Baez are all set to be free agents come the end of the season. Had the team struggled out the gate and been way off the pace in the division, the decision to trade some of them would have been straightforward. With the team competing, that is no longer the case.

“I think it could very well change their plans with Bryant, Rizzo and Baez,” said Matt Clapp, the managing editor at Awful Announcing, a sports media site. “Or at least in terms of trying to keep at least one or two of them. They have what appears to be a legitimate starting pitcher in Adbert Alzolay and there are a lot of pitchers making strong impressions in the minors. This is with a lot of money coming off the books over the next few years, too. So if you’re able to fill out a lot of roster spots cheaply, it allows you flexibility to spend bigger in other areas.”

One of the reasons why expectations were tempered was largely due to the trade that saw starting pitcher Yu Darvish and catcher Victor Caratini traded to the San Diego Padres for pitcher Zach Davies and a number of minor league prospects.

The move was seen as a cash dump and a sign that the Cubs were entering into another rebuild mode.

“At the time of the trade, I wrote that it was signaling a fire sale to the rest of the league,”  Fangraphs writer Sara Sanchez said. “It’s like they tied David Ross’ hands behind his back and said “win without your Cy Young candidate.” Ross rose to the challenge.”

A potential rebuild would have been simpler, and easier to stomach for the fans, if the team was struggling. They were at the start of the season but now have things clicking. In a way, it’s put owner Tom Ricketts and Jed Hoyer, president of baseball operations, in a bit of a bind ahead of the July 31 trade deadline.

“It’s an awkward position, if this keeps up, but it also provides them more options,” Clapp said. “Additionally, they can be buyers without putting a big dent in their long-term plans. You can add depth pieces every deadline without giving up major dollars or prospects. See the Nick Castellanos trade for example.”

With the Darvish trade, the plan seemed to be stockpiling on prospects — a plan they may have stuck to when it came to some of their pending free agents if the team was floundering. If the Cubs can continue on a similar pace, there is a strong likelihood that they will be buyers as the trade deadline approaches. 

“If you’re in July and getting closer to the trade deadline and still in a good position, I don’t see any scenario where you can trade these guys,” Stebbins said. “Two players that would always be brought up are Bryant and Craig Kimbrel. If they’re at this pace, if they’re in first place, or tied, and 15 games above .500, I just don’t see a scenario where you trade Bryant or Kimbrel. What would that say to your team? What message would that send, in a year where they look like a true contender, giving away two of your good players?”

The question going forward is whether or not the Cubs can continue on their current pace, or close to it, and be a contender come July where they can go out and acquire more pieces for a potential playoff run.

“It is certainly true that the June schedule looks rough as the Cubs will try to run the gauntlet through the NL West on the road,” Sanchez said. “But it’s worth recognizing their schedule to date has not been easy. They’ve already played the Mets, Braves, Dodgers, Padres and Cardinals. They are 13-8 against the top of the NL and five of those losses came against the Braves. That is a .619 win percentage against the top of the division and I’d put that up against any team in baseball right now.”

The Cubs perhaps find themselves in a position they were not expecting to be in. Regardless of the competitiveness — or lack thereof — of their division, they are near first place. Their core, which struggled last season, is bouncing back in a season where they might have felt that they needed to prove themselves.

“I think the whole front office mentality, this core that has underwhelmed in recent years— they made the playoffs a couple times but haven’t gone deep since 2017— it was a matter of proving it,” Stebbins said. “I wouldn’t say the ownership is surprised but they’ve definitely played above a lot of people’s expectations, whether that includes the front office, I don’t know. But at the very least, [the players] are proving it.”