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The Chicago Cubs have already started making noise in free agency, beginning with a familiar bullpen arm. Jacob Webb has agreed to return on a 1-year, $2 million deal, with a $4 million team option for 2028. This move, added…

The Chicago Cubs reportedly hold strong interest in pursuing free-agent ace Tarik Skubal to reinforce their starting rotation this winter. Chicago has already retained reliever Jacob Webb on a one-year, $2 million contract that includes a $4 million team option for 2028. According to reporter Jeff Passan, the Cubs want Skubal, who could command a contract exceeding $300 million to $400 million in free agency.
Cubs president of baseball operations Jed Hoyer stated that pitching acquisitions will dominate the front office's offseason focus following an 89-73 campaign. The Cubs used 14 different starting pitchers in 2026 and posted a 4.12 ERA before suffering a postseason sweep against the San Diego Padres.
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