Cubs fail to land another high-ceiling pitcher in a trend fans are tired of

With the Chicago Cubs remaining in the market for a high-leverage relief pitcher, even after their signing of Phil Maton, one free-agent option that made the most sense was Ryan Helsley. After being traded to the New York Mets at the MLB trade deadline, Helsley struggled, leading to the impression that he would be a cheaper alternative to the top names in the free-agent market for closers.

That proved to be true as Helsley inked a two-year deal with the Baltimore Orioles worth $28MM. Assuming the Cubs weren't shying away from another multi-year deal, that was the expected money for the tier of pitchers they were shopping. However, if Helsley signed with the Orioles, it would be fair to wonder if the Cubs even made an offer.

Rumored Cubs' target Ryan Helsley is signing a two-year deal with the Baltimore Orioles.

Days after missing out on Dylan Cease, the idea of the Cubs also missing out on Helsley is likely going to reunite Cubs fans with the uneasy feeling they have when talking about the team's offseason pursuits. All too often in recent years, it seems that the Cubs miss out on the initial targets they identify during the early months of the offseason.

Of course, already having Maton in the hold, it would be fair to suggest that Jed Hoyer and Co. may not have attacked their pursuit of Helsley with the same sense of urgency the Orioles had. Beyond taking a wrecking ball to their bullpen at the deadline last season, the Orioles also needed a replacement for Felix Bautista, who is expected to miss most of the 2026 campaign.

After the signing of Maton, the Cubs were left with around $40 million in payroll space before reaching the first level of the luxury tax. Helsley's deal would have taken that number below $30 million, and all but confirmed the team would be addressing their need for a starting pitcher through the trade market.

While that still may be the case, there are still several starters on the free-agent market who could fit the Cubs' spending strategy. In particular, Michael King makes a ton of sense for what Chicago is looking for.

Back to bullpen options, with Helsley off the market, the Cubs may turn their attention to a reunion with Brad Keller. Otherwise, former Tampa Bay Rays closer Pete Fairbanks would be an ideal option.