After falling short of the postseason, how do the Chicago Cubs take a step forward organizationally for 2024?

When Dansby Swanson signed his seven-year, $177 million deal with the Chicago Cubs in December, he came to the organization expecting a commitment to winning.

Year 1 fell short of the playoffs, and how the Cubs stumbled down the stretch with poor play ended the season on a sour note. As the organization dissects the underlying issues of what went wrong over the final three weeks, they won’t dismiss the positives that came out of a winning season.

“With how we finished people are going to think it’s further off than it actually is,” Swanson said after their final game. “There’s a lot of really, really talented players not only here but obviously in the lower levels that can contribute and then offseason free agency, there’s plenty of moves that can be done there as well that could really get us over the hump and rolling in the right direction. But definitely a good step this year, definitely confident with things moving forward.

“We proved a lot for probably what most people consider not worthy and we were just about a game, game and a half or two or whatever short, so there’s plenty of optimism and I think a lot of guys are wired the right way to come back and be ready to roll next season.”

The Cubs, though, can’t afford to take a step back from adding talent in the offseason. To get into the postseason in 2024 and continue building a legitimate World Series contender, acquiring another power hitter should be a priority, even if they do re-sign Cody Bellinger. Addressing their corner infield positions needs to be part of that equation, and pitching depth must be improved.

“I was hoping to have less of October to do offseason planning, but certainly we’ll get right to work,” president of baseball operations Jed Hoyer said Tuesday, “and spend a lot of time now that we’re not in the fight, get a chance to break down exactly the things that we need to improve.

“The shell of a really good team is there. Obviously we have to make additions and we have to find ways to improve, but I feel really good given where we were a year ago.”

The Cubs scored the third-most runs in the National League behind the Atlanta Braves and Los Angeles Dodgers while featuring among the best in run prevention, sitting in the top seven in the majors for Outs Above Average (OAA) and Defensive Runs Saved (DRS), led by Swanson and Nico Hoerner up the middle. But both of those areas faltered in the final three weeks, and a banged-up bullpen wasn’t able to hold up.

The Cubs have a core to build around that creates positional and cost certainty. With Swanson in the fold for six more years and Hoerner, Ian Happ and Seiya Suzuki’s contracts going through the 2026 season, the Cubs feature a great foundation to build on. Adding to that on the pitching side: Justin Steele, who won’t reach free agency until after 2027 to give them a staff ace as one of the organization’s most important developments, and Jameson Taillon, who posted a 3.38 ERA in his last 16 games, provides experience and rotation stability with three more years on his contract.

“We’ve got to find the pieces to put with them and hopefully some of those pieces come internally,” Chairman Tom Ricketts said on the final day of the season. “I mean, we’ve got a lot of good young players and hopefully some will be ready to go next year so that we can bring homegrown talent to supplement the guys that we have out there. That’s the ultimate way you maintain consistency and try to stay in the playoff hunt for years to come.”

The Cubs were the first team in franchise history to go from 10 games under .500 to 10 games over in the same season. That distinction created mixed feelings within the clubhouse on how to view the season.

For Taillon, falling just short of making the playoffs “hurts probably more” because of the run they made, adding, “I really feel like we could have been that team for a full year, which makes it hurt.”

Although he was on the Cubs’ 2020 postseason roster, Hoerner still is waiting to play in his first playoff game after not appearing in either of their losses to the Miami Marlins. He was not yet in a reflective space after the Cubs’ elimination from position contention about their ups and downs over the 162-game season. But he said of the sting from missing out and how they rallied to even be in postseason contention: “Both things can be true where I do see the direction that we’re headed and I’m really excited and optimistic but what I feel in the moment is definitely stronger.”

The Cubs notably featured five World Series champions, but beyond that group, most of the roster had never played in a postseason game. After missing out this year, they must find value in getting a glimpse of the stakes that are only further elevated in the playoffs and use their September experience to take the next step in 2024.

“The fact that we played very meaningful games in September could be a lesson for guys,” Taillon said after the Cubs were eliminated in Milwaukee. “Like, the season’s long and it seems even longer when every game matters, every pitch matters. You saw the last two weeks, it came down to little plays. It came down to one play here, making one pitch here, one swing there. When you’re out of it in September, there’s less pressure.

“It’s probably a lesson throughout the entire roster, condition as well as you can and stay locked in for every single game, but it’s also going to be a good building block for young guys being up here.”

Added Kyle Hendricks: “We kind of ran out of some steam it seemed like here at the end, so it’s just mentally having that preparation knowing we’re going all the way to the end of October, into November if needed. It’s such a mental grind through the whole year that that’s where it really affects you more. We learned a lot of what it means being in this many meaningful ballgames, how much of a toll it takes on you throughout the course of the year.”


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