Chicago Cubs make pivotal bullpen decision before free agency sweepstakes

The Chicago Cubs will be connected to all the big name starting pitchers available in free agency. But they haven’t forgotten their bullpen either.

Chicago finished the regular season ranked 13th in bullpen ERA with a mark of 3.90. With their sights set on a deep playoff run, the Cubs will look to add even more firepower to relief corps. They took one giant leap already towards fixing the bullpen when they acquired Ryan Zeferjahn at the trade deadline.

In terms of free agent relief pitchers, Adrian Morejon, David Bednar and Sean Newcomb are at the top of the list, at least based on 2026 WAR. All three will be highly coveted options on the open market. If the Cubs are going to sign any, they must be prepared to pay up.

Before that opportunity comes, Chicago made sure to take care of one of their own. The first domino of the Cubs’ bullpen puzzle has fallen.

Chicago Cubs re-sign Jacob Webb

Chicago Cubs Jacob Webb — Aug 22, 2026; Seattle, Washington, USA; Chicago Cubs pitcher Jacob Webb (71) leaves for the dugout after surrendering a walk-off home run against the Seattle Mariners during the ninth inning at T-Mobile Park. Mandatory Credit: Joe Nicholson-Imagn Images

Chicago has signed right-hander Jacob Webb to a new one-year, $2 million contract, via Robert Murray of FanSided. The Cubs will have a $4 million club option for the 2028 season.

“Right-handed reliever Jacob Webb and the Chicago Cubs are in agreement on a new one-year, $2 million contract that includes a $4 million club option for 2028 ($500K buyout), according to a source familiar with the deal,” Murray wrote.

Webb joined the Cubs on a one-year deal heading into the 2026 campaign. Over his first 68 games with the team, the righty held a 3.36 ERA and a 73/25 K/BB ratio. Webb struggled mightily down the stretch, holding a 7.36 ERA over his last eight appearances. Still, he was a consistent force who produced dominant stretches. Through his 11 outings in July, Webb recorded a perfect 0.00 ERA and a 10/3 K/BB ratio.

The Cubs are sure to make further additions to their bullpen. But they couldn’t let Webb leave the Windy City. If the right-hander keeps up his strong play, his tenure in Chicago could last even longer.

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