The Chicago Cubs desperately need starting pitchers. You know it. I know it. Jed Hoyer knows it.

Yes, the organization did attempt to address this clear area of weakness at the MLB trade deadline. They went out and moved multiple big-name prospects for veterans Kevin Gausman and Clay Holmes. Both proceeded to pitch well during their couple of months as a Cub, but both also happen to be heading straight into free agency this offseason.

On top of that, Shota Imanaga just wrapped up the final year of his deal, while the health of Justin Steele and Cade Horton remains uncertain. It creates some pretty major concerns on the mound for a franchise that still has every intention of pushing for a deep postseason run. After all, their group of position players is built to win now.

The good news is that the Cubs are expected to have plenty of money to spend in the coming months. They should be able to go after some of the top names on the market, if they choose. But we also know this isn't the only way for them to address the obvious roster hole. If anything, more often than not, it's a trade or two that solves the biggest problems for MLB teams.

Reid Detmers remains a fascinating target for Jed Hoyer and Company. He is coming off another strong season with the Los Angeles Angels, recording a 3.36 ERA with a strikeout rate of 28.5 percent. No pitcher was connected more to the Cubs at the trade deadline than Detmers, only for Chicago to strike a different deal with LA. The trade saw Ryan Zeferjahn sent to the North Side in exchange for Moises Ballesteros and prospect Mason McGwire.

Nevertheless, deadline conversations can serve as a precursor to what we see in the offseason. The Angels need young talent. The Cubs need proven pitching. The fit is too apparent for the sides not to talk again. We also can not ignore a recent rumor from a local Cubs source. If a Detmers trade was as close as this new report suggests, why wouldn't the two try to pick up where they left off this winter?

Was Reid Detmers to the Cubs Nearly a Done Deal?

During a recent post on The Cub Report, long-time Cubs blogger Arizona Phil provided some insight on the Reid Detmers rumors at this previous deadline.

Arizona Phil states that he heard from multiple sources that there was a deal in place for Detmers between the Cubs and the Angels. However, things eventually fell through when the Angels decided to reject the medicals on Chicago prospect Jaxon Wiggins and chose not to work out another version of the trade.

Arizona Phil also goes on to state that a deal to send Clay Holmes to the Diamondbacks also fell through around the same time, opening the door for the Cubs and Mets to talk. Chicago was apparently willing to send Jefferson Rojas in the Angels trade as well, but pivoted to Holmes when the Wiggins medicals were rejected.

For a complete look at what Arizona Phil had to say, I encourage anyone to read the full post on The Cub Reporter. Of course, whether this is completely accurate is something we'll never truly know, but it would potentially describe why popular Chicago Cubs site Bleacher Nation initially reported that the Detmers trade was a go. In other words, it may have genuinely fallen through at the 11th hour.

If that really is the case, then it only gives us more reason to believe that talks could be revisited in the very near future. The Cubs were clearly very serious and intentional about getting their hands on Detmers, and why would that change now? It's not as if they found some kind of answer in the postseason. If anything, the last few weeks of 2027 only further underscored their need for starting pitching and guys who can throw strikes.

Of course, it's notable that Jefferson Rojas is no longer inside the organization, specifically if he was a main part of that deal. But is there a world where the Angels are interested in Matt Shaw, who is starting to feel expendable? Heck, rumors swirled a few months back that they wanted a young catcher. Moises Ballesteros checked that box, but what if Owen Ayers was suddenly on the table?

At the end of the day, it feels inevitable that the Cubs make some kind of big move for a starting pitcher. Perhaps that happens during free agency, which may even include re-signing someone like Holmes. But Detmers is pretty clearly a player this front office was serious about in the recent past, and some of the legwork may already be done to get a trade across the finish line.