Will the Cubs Sign Tarik Skubal? A $184M Record Meets a $350M+ Price

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Will the Cubs sign Tarik Skubal? Named a suitor, but not a top-tier fit

The Cubs are a named possible suitor for Tarik Skubal, but they are not the favored destination in Kalshi's Tarik Skubal Next Team market. Former Cub Anthony Rizzo called Chicago an "obvious fit" for the two-time AL Cy Young winner, according to ClutchPoints. The Athletic's Jim Bowden, however, ranked Skubal the No. 1 free agent and listed his "best team fits" as the Mets, Dodgers and White Sox, per Yahoo Sports.

Money sharpens the gap. The largest contract in Cubs history is Jason Heyward's eight-year, $184M deal from 2016, while Bowden projects Skubal at $350-500M. In the market, Chicago C fell from roughly 14% to 4% over three days. Bowden's rankings and projection are editorial forecasts, not market odds.

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Chicago C's drop in the Tarik Skubal Next Team market: 14% to 4% in three days

The sources do not establish what triggered the repricing. Rizzo's comment ran Oct. 23, and the Yahoo item recapping Bowden's rankings was dated Oct. 27. Both are existing commentary rather than events tied to the timing of the slide.

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Chicago C traded at 4% on Oct. 29, 2026, down from 14% three days earlier. The market resolves March 25, 2027.

The Cubs already had one chance to acquire Skubal and passed. Jed Hoyer reportedly spoke with Detroit's Scott Harris before the August deadline, but Chicago acquired Kevin Gausman instead. Skubal went to the Dodgers for Zyhir Hope, River Ryan and Brady Smith, then lost his Dodgers debut 5-1 at Wrigley Field on Aug. 4, the Chicago Sun-Times reported.

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The Cubs' $184M contract record versus Skubal's projected $350-500M price

Chicago has never paid a player more than $200M, and Heyward's $184M remains the franchise high, Yahoo Sports noted. Bowden's low-end projection of $350M is nearly double that record. Skubal is also expected to want the top pitcher salary in baseball, a mark currently held by Yoshinobu Yamamoto's 12-year, $325M deal.

That history is a ceiling, not a rule. The Cubs face real rotation pressure: Shota Imanaga, Gausman and David Peterson are already free agents, and Matthew Boyd ($15M mutual option) and Clay Holmes ($12M player option) are expected to join them. Skubal posted a 2.72 ERA, 0.964 WHIP and 186 strikeouts in 158 ⅔ innings across Detroit and Los Angeles in 2026.

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Tarik Skubal Next Team

Each outcome's chance, from what traders are paying right now on Kalshi.

Chicago CIn this story

2%

Kalshi50.00x2¢

New York M

62%

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Los Angeles D

17%

Kalshi5.88x17¢

Los Angeles A

6%

Kalshi16.67x6¢

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The case for Chicago has not disappeared. Rizzo's endorsement and the Cubs' place on a suitor list that also includes the Tigers, Phillies, Blue Jays and Red Sox keep them in the conversation. None of the sources say whether the Cubs will exceed their record to land him.