Cubs Do It Again: A Fine, Boring and Kind of Annoying Free Agent Signing

Honestly, more than anything it’s the timing. I mean, if the Cubs end up signing Tatsuya Imai this offseason or get Kazuma Okamoto, or who knows maybe they get wild and sign Bo Bichette, then it’s all good signing Jacob Webb a few days before Christmas. But they haven’t done that, so while acquiring another decent reliever on the cheap is obviously a fine move by the Cubs, it is annoying.

Don’t get me wrong, this is petty as hell. I’m not even a Jed Hoyer hater and defend most of his moves, but strictly speaking as a fan who wants to be excited over player I can’t lie, Jacob Webb ain’t doing it for me. That being said, if the Cubs’ trend continues, then we got another solid pitcher who you haven’t heard of that will be getting big outs throughout the 2026 season out of the bullpen.

Whoever was scouting the Texas Rangers for the Cubs this past season is having an awesome offseason because Webb is now the third relief pitcher the Cubs have signed since November that threw for the AL West squad. Webb joins a Cubs bullpen that also includes Phil Maton and Hoby Milner.

Webb, who originally broke into the majors with the Atlanta Braves in 2019, hasn’t had a long track record in MLB, but when he’s pitched in the big leagues the right-hander has always delivered strong results. In 2025, Webb recorded a 3.00 ERA in 66 innings of work with a 1.03 WHIP in 55 appearances out of the Rangers’ bullpen.

Since getting a real opportunity to be a contributor in the bullpen beginning in 2023, Webb has posted a 3.22 ERA in 176.1 innings.

This signing does follow a similar playbook that the Cubs seem to target in the offseason to help fill out their bullpen. Yes, cheap, but in terms of how they get to the results, Webb doesn’t really throw that hard, averaging 93.5mph with his fastball, he doesn’t have big strikeout numbers as he posted a 21.7 K% in 2025, and probably what makes the Cubs love Webb’s profile the most, he doesn’t give up hard contact, allowing a 5.9 barrel% last season.

Webb has had issues with walks in the past, but at least he got them in check to a point in 2025, lowering his walk rate to 7.1% after it stood above 10% in the previous two seasons. Yet, the strikeout rate has declined since 2023, and what really makes me nervous about a pitcher like Webb is that while he does a good job of avoiding hard contact he still falls victim to the home run ball.

In 2025, Webb allowed 10 home runs in 66 innings. That was the 13th highest home run rate among right-handed relievers in MLB out of 99 qualified pitchers. Plus, the .219 BABIP against Webb suggests that he was certainly getting some luck throughout the season. But again, it’s one of those things where the Cubs are counting on the defense to help out the contact-oriented pitchers to get those outs.

Hey, I love great defense and we should appreciate the group assembled on the field for the Cubs. But, man I would also love to get more pitchers who can come in and strike out the side, making it look easy.

I guess the annoyance stems back to believing that the Cubs would go out and sign that big arm for the bullpen. Add more velocity. Jacob Webb is going to be fine, might even be really good, so this is more bitching about wanting more, which I do think is fair, but it doesn’t make the Cubs’ approach wrong.