Kyle Tucker has transformed the Chicago Cubs’ lineup since arriving via a blockbuster trade from the Houston Astros this past offseason.

The three-time All-Star ranks among baseball’s elite hitters, posting a .301/.410/.578 slash line with five home runs, eight doubles, 19 runs scored, 19 RBI, and a league-leading 16 walks.

Tucker approaches free agency positioned for a substantial contract, with negotiations likely starting around $500 million following Vladimir Guerrero Jr.’s recent extension with the Toronto Blue Jays.

The Cubs have been viewed as frugal in recent years as they rank 12th in baseball with an estimated luxury tax payroll of $216 million in 2025. Their financial commitments drop significantly to $123 million for the 2026 season.

Tucker’s offensive production has helped propel the Cubs to first place in the NL Central with a 12-9 record. As his potential departure looms, industry voices are sounding alarms about what failing to retain him would mean for Chicago.

MLB executive: Will go down as ‘all-time terrible trade’ if Chicago Cubs don’t sign Kyle Tucker

In a conversation with MLB.com’s Mark Feinsand, an anonymous executive offered a stark assessment.

“If the Cubs don’t extend him, that may go down as an all-time terrible trade,” the NL executive told MLB.com.

The Cubs acquired Tucker by sending All-Star infielder Isaac Paredes and prospects Cam Smith and Hayden Wesneski to Houston. The situation mirrors the New York Yankees’ experience with Juan Soto, who departed after one season to sign a record $765 million deal with the Mets.

Losing Tucker would disappoint a Cubs fan base eager for October baseball after four consecutive seasons without playoff appearances. Securing his services would represent a crucial first step toward rebuilding a championship-caliber roster.