The Cubs came out of the trade deadline with rotation help, but one of the near-misses on the board would have looked a lot different for them by now. Chicago was involved in talks with the Boston Red Sox for left-handed starter Connelly Early, and if that deal had gotten across the finish line, it could have changed the Cubs’ 2026 picture in a major way.
According to Pat Ragazzo, the Cubs were in the mix for Early before the Washington Nationals jumped in and got a deal done on July 25, eight days before the deadline. Boston sent Early to Washington in a surprising one-for-one swap for infielder Curtis Mead, and the Nationals beat Chicago to the punch.
That matters because Early has had a strange path since then. The 24-year-old had already been a name to watch in trade chatter, especially after the Cubs signed Alex Bregman and left Matt Shaw without a clear starting job. Early made only four appearances in his late-season call-up in Sept. 2025, but he flashed real bat-missing ability with 29 strikeouts in 19.1 innings.
The appeal was obvious beyond the stuff. Early is under team control through the 2031 season, so this wasn’t just about one arm for one stretch run. It was a cost-controlled starting pitcher with upside, and that kind of profile tends to get teams moving fast.
Still, the timing and the health picture make this one easy to view through a Cubs lens. Heading into the final three weeks of the regular season, Early still hasn’t pitched for Washington. He last faced the Nationals on June 30 before going down with an elbow injury, later landed on the 60-day IL in late August, and is only set to begin a brief rehab assignment this week.
That’s where the “very bad for 2026” part comes in. Chicago could have been the club holding the bag on a pitcher who hasn’t taken the mound for Washington yet, while also giving up real pieces to get him.
The source points to Shaw or Pedro Ramirez as the kind of players Boston may have been after in those negotiations. Shaw was already dealing with a wrist issue at the deadline, and Ramirez has since become more important for the Cubs, first as a backup infielder and then as a starter after Dansby Swanson landed on the injured list.
Shaw’s return hasn’t exactly transformed the Cubs, but moving him for Early would have been a painful swing this year. And if Chicago had been more aggressive in that pursuit, it might have altered the rest of its deadline approach too, possibly even taking Holmes off the table.
Holmes is part of the reason the Cubs could walk away feeling good about what they did do. He was roughed up in his last start, giving up eight runs in 4.1 innings against the Miami Marlins on Sunday, but since the trade deadline he has looked elite in a Cubs uniform.
The Red Sox-Nationals deal has gone nowhere fast for both sides. Early still hasn’t returned from the injured list, and Mead managed just two plate appearances for Boston before a pitch struck him and broke his left wrist. Mead is hoping to make it back this season.
For the Cubs, that’s the kind of deadline miss you can live with. Early would have cost them real talent, and so far he hasn’t thrown a pitch for Washington. Sometimes the cleanest win is the trade you never make.
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