MESA, Ariz. — Three and a half years after deciding to retool their major and minor league rosters at the 2021 MLB trade deadline, the Chicago Cubs believe this is the season it should pay off with a playoff appearance.

The Cubs haven’t hidden their sense of urgency that has separated this winter from recent ones. From the moves the front office made to what has been said as the team reports to camp, Chicago has one thing in mind: playing October baseball for the first time in half a decade.

“I think we’re in a competitive window,” president of baseball operations Jed Hoyer said when the Cubs reported this week. “I think we’ve gotten better each year. I think we’re at a place where we have a chance to be really good and we’ve been trying to really maximize our resources within our budget to make sure that we can do that.”

As they enter the heart of what they believe is their next contention window, the Cubs aren’t spending like the Los Angeles Dodgers and New York Mets (hence a slower rebuild after moving on from the 2016 championship core) but they aren’t the Pittsburgh Pirates or Milwaukee Brewers either. The Cubs were one of nine teams with a payroll that exceeded the luxury tax limit last season and six of those teams reached the postseason. The Cubs were not one of them, and while ownership wants that to change in 2025, they were outbid by the Boston Red Sox for top remaining free agent Alex Bregman.

The team still is littered with $20 million-caliber players even without Bregman, such as newly acquired outfielder Kyle Tucker, whose arrival this winter signaled the shift in strategy. The Cubs traded three players, including a recent first-round draft pick, for the soon-to-be free agent Tucker.

“You don’t make a trade for Kyle Tucker if you don’t feel like you have a really strong team going into that year,” general manager Carter Hawkins said. “And so certainly I would say objectively we’ve improved year over year in terms of just the talent level that’s on the field — and in the three-plus years I’ve been here, this is certainly the most talented team we’ve had.”

The projection systems agree, with predictions as high as 87 (ESPN BET) to 90 wins (PECOTA) and a National League Central-best 84.9 wins that gives them a 39.3% chance of winning the division, according to ESPN’s Bradford Doolittle. Whether they reach the loftiest projections, the team is primed to take a leap forward in Craig Counsell’s second year as manager after back-to-back 83-win seasons.

“It should feel like this all the time,” Counsell told ESPN earlier this week. “From that perspective, it makes me happy that we have high expectations.

“When you trade for a great player and he has one year left on his contract, that tells you a lot.”

Counsell acknowledged the team had to “rebuild a few things” after trading former stars Anthony Rizzo, Kris Bryant and Javier Baez in 2021. The process ate up a lot of the five-year contract Hoyer signed after Theo Epstein stepped down in November 2020. With this season left on his deal (and no extension imminent), Hoyer is well aware of the consequences this year could have on his future.

“I’ve been here for 14 years and sort of generally in my career, I haven’t had much uncertainty,” he said last weekend. “And so I think with uncertainty does come a level of anxiety. I think that would be a lie to say that it doesn’t.”

That feeling wasn’t lost on his handpicked manager. It wasn’t long ago that Hoyer shocked the baseball world when he plucked the well-regarded Counsell from division rival Milwaukee and made him the richest manager in the game. Now Hoyer’s fate — at least in part — is dependent on Counsell getting the best out of the team the front office has built.

“That makes it fun in my opinion,” Counsell said. “It provides a lot of clarity. And I’ve said that to Jed. It’s like, ‘Let’s go.’ I think that’s how he sees it. It can give you a lot of clarity in how you do things. We’re excited to try and do it together. I hope he’s here for a long time.”

As the Cubs’ position players report to camp Friday, here is what could make or break a playoff-caliber season in Chicago.

The stars have to play like stars

Despite the talent bubbling up at Triple-A and a new group of depth players on the major league roster, Counsell acknowledged his best players need to carry the day. Perhaps that’s the case for any roster, but with a team projected in the mid-80s win range that is often near the bar for playoff entry, there is little room for underachieving.

“Everything matters when you’re trying to get extra wins,” Counsell said. “You get it from wherever you can. Every decision is trying to add to that. … We’re going to rely on our regulars. We need production from our regulars, offensively and defensively.”

That wasn’t always the case last season. High-priced shortstop Dansby Swanson may have lost the Gold Glove award with his play in April, then slumped at the plate midseason. Swanson was battling a sports hernia injury that he didn’t disclose until after the season, so his ramp-up will be a little slower this spring. Same goes for second baseman Nico Hoerner, who had flexor tendon surgery on his throwing arm. He could miss a few days at the start of the season. Both are going to be counted on, especially if rookie Matt Shaw is the starting third baseman.

In the outfield, Ian Happ has put up reliable 115 to 120 OPS+ seasons while dynamic center fielder Pete Crow-Armstrong is just beginning to figure out how dangerous his skill set can be. And if this is the year Seiya Suzuki — now the designated hitter — can put together a solid six months, the Cubs offense could explode.

But the key to the lineup will undoubtedly be Tucker. He has the ability to impact a game in a way no other Cub can — and it comes in his free agent season.

Before they traded for Tucker, Hoyer raised eyebrows when he said his players needed to “exceed” expectations, leading fans to wonder why the team wasn’t just acquiring players with higher ceilings. Now that the club has one, it needs the best version of him with others filling their roles. It’s a good offense that could be great if it clicks.

Who’s on third?

Bregman wasn’t one of the Cubs’ primary targets entering the offseason, so perhaps they’re not overly disappointed or surprised he’s not on their team. But his potential fit at third base had fans salivating as the winter played out. Well at least until Wednesday night, when Bregman signed a three-year, $120 million deal with the Red Sox.

Adding Bregman would have pushed those projection models over 90 wins and given the Cubs a clear path to the postseason. The road to October remains a little less clear with Shaw the likely Opening Day third baseman, but the Cubs believe he could open some eyes around the league.

Shaw is the No. 23-ranked prospect in all of baseball entering the season, according to ESPN’s Kiley McDaniel, but comes in a little undersized for the hot corner. At 5-foot-9, he has power that would certainly play at second base, but he’ll be relied on to provide pop playing at a corner.

Michael Busch (who hit 21 homers in 152 games last season) is also on the smaller side for his position at the other infield corner as a 6-foot-1 first baseman.

“It’s not the biggest group on the corners,” one scout said. “But that doesn’t mean they can’t slug. Busch outperformed some expectations last year.”

Not having traditional sluggers at the corners also means the true power hitters on the team — Tucker, Swanson, Suzuki and Happ — are going to be relied on even more.

The bullpen must deliver

The Cubs blew six games that they led entering the ninth inning last season — third most in baseball. Six is also exactly the number of games Chicago finished behind the third NL wild-card team. In overhauling their bullpen for 2025, the urgency to lower that number came by adding experience.

The Cubs acquired five pitchers — Ryan Pressly, Eli Morgan, Ryan Brasier, Matthew Boyd and Caleb Thielbar — who took the mound in the playoffs over the past two seasons and four of them pitched last October.

“When I looked at the roster in spring training this year, compared to last year, I think that was the No. 1 thing,” pitching coach Tommy Hottovy said. “It’s not only the number of bodies but the amount of major league caliber pitchers that have been there and done that.”

Acquired from the Houston Astros late last month, Pressly is the biggest name and could fill a crucial role for a bullpen searching for a competent closer after cycling through one failure after another last season. There were plenty of ninth-inning options on the free agent market this winter, but budget constraints along with Chicago’s overall feelings on many of them outside of Tanner Scott (who chose the Dodgers over the Cubs last month) led to a trade for Pressly.

“I want to be somebody that all these guys can lean on,” Pressly said in his introductory news conference. “Any questions that they have, on or off the field, I want to be that guy for them.”

Counsell added: “When you pitch in those situations, your team is like 10 minutes away from a win. That’s what makes it feel like more for guys that pitch in that situation. We rightly assign some credit for guys with experience there.”

With a revamped lineup and bullpen entering a crucial season, the Cubs hope they are just a smooth ninth-inning away from enough wins to be one of the last teams standing in October.