The Chicago Cubs aren’t exactly limping—but they’re not sprinting, either. They have an impressive 53-35 record, and a .593 winning percentage, leading the NL Central. However, the postseason is slowly creeping in, and the Central is far from locked, so the team’s fate hangs on decisions made in the coming weeks. Still, the franchise shows definite promise, which ESPN’s Jesse Rogers and analyst Tim Kurkjian have discussed at length.

See, Chicago’s current position is precarious. They’re at the top of the division, but the offense shows up in spurts and the bullpen? It’s more of a question mark than a weapon. That 2016 magic feels distant, and that’s exactly why ESPN insider Kurkjian urges the Cubs to act fast.

“These first-place teams, especially ones with only a slight lead like the Cubs, are thinking two different tracks,” Kurkjian stated on the ‘Baseball Tonight’ podcast. “One: we’ve got to add near the deadline to ensure we get to October. But if we want to win in October? That’s a different kind of addition.” He pointed to 2016, the year Chicago Cubs had traded for Aroldis Chapman despite having a perfectly reliable closer, Héctor Rondón. Why? Because “they had a 99% chance of making the playoffs, but they knew Chapman would help them in October. That underscores the idea: starting pitching gets you there, bullpens win it,” Kurkjian highlighted.

Rogers agreed with the sentiment, emphasizing how postseason baseball has evolved, but the core aspects have survived. “Twenty-five years ago, Davey Johnson told me winning in the postseason was bullpen and bench. And that’s more true today than ever, especially the bullpen part.” Referencing the Los Angeles Dodgers’ use of openers and elite relief postseason usage, Rogers adds, “The Cubs are in a great position because of how they swing the bat. They’re the second-highest-scoring team in the Majors. But if they add a couple of impact relievers, they could be a very, very dangerous team in October.”

Well, the Cubs would benefit from additional impact arms to their bullpen, mitigating late-inning collapses and holding leads more effectively. Also, managers won’t be limited to overusing top relievers—so less fatigue, and more consistency. And on an interesting note, the Cubs have a history of identifying valuable relievers, either through smart trades or low-risk signings. Perhaps, they have someone in mind this time as well.

Cubs target experienced relievers ahead of playoffs

October baseball is a different beast from the regular season. Despite Chicago having the second-best bullpen performance over the past two months, manager Craig Counsell has acknowledged bullpen wear and tear. The Cubs have shown strong instincts with targeted acquisitions before (like Eli Morgan this offseason), and they may be eyeing a similar approach here.

Sources say the Windy City would prefer experienced relievers—flamethrowers and swingmen alike—over risky low-leverage options. Pete Fairbanks from the Tampa Bay Rays has surfaced as a strong candidate. Fairbanks’ power pitching could offer the ideal midseason fix. The front office is also evaluating other names, including Mitch Keller. According to USA Today’s Bob Nightengale, the Cubs, and Pittsburgh Pirates have been locked in “serious trade talks” for more than a week regarding Keller, who is in the second year of a five-year, $77 million contract signed before the 2024 season—even as he endures a challenging campaign this year.

Beyond the bullpen, third base has also emerged as a concern. The fanbase has pointed to the need for a switch-hitting infielder who can handle third-base duties and hit lefties. With inconsistent production at third and a lack of platoon advantages on the roster, there’s a need for offensive reinforcement—and to remedy that, the Cubs could use Eugenio Suárez. As he’s nearing 30 home runs before the All-Star, Suárez could be just the bat the Cubs need. With the Diamondbacks facing roster crunches, he might become available.

There’s also a push for reliable off-bench power, something that’s cheap but could pay off in key moments. Someone like Jorge Soler has emerged as a consideration—someone who could serve as a backup slugger, late-game pinch hitter, or injury insurance. If the Cubs want to seriously contend, it’s about making smart decisions where they’re needed.