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The Chicago Cubs are staring down what many believe will be a rougher than rough market ahead of the August 3 trade deadline.
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With tight races in both leagues and many expected sellers possibly becoming buyers at the last minute, Jed Hoyer and the Cubs front office could find themselves priced out of the bidding for a much-needed high-end starting pitcher and closer-capable reliever. Unless, of course, they’re willing to overpay.

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Jim Bowden, former MLB exec and current analyst for The Athletic, recently listed a Cubs-Kansas City Royals deal he’d like to see—one which he acknowledges as an overpay from Chicago.
Per Bowden:
“In this deal, the Cubs would add Wacha, 35, who made the AL All-Star team this year and is controllable through 2027 with a team option for 2028. He has posted sub-4.00 ERAs each of the past five years (including this one) and still has a special changeup and unique downward plane to his pitches.
In return, the Royals get two young bats who can’t crack the Cubs’ starting lineup in Shaw and Alcántara. Shaw, 24, can play second base, third base and corner outfield. As an everyday player, he projects to have 15-20 home run power. Alcántara, 23, has never been given a legitimate chance with Chicago, but he’s having another strong season in Triple A.
I think this deal is an overpay by the Cubs, but it should be worth it to land a veteran starter like Wacha, especially given that there are so few starting pitchers on the market right now.”
And, yeah, this would be considered an overpay given the high ceilings of both Shaw and Alcantara.

The 24-year-old Shaw could probably be playing every day third base or second base for many—if not most—major league teams right now. With the Cubs’ signing of Alex Bregman this past offseason and the extension of Nico Hoerner, Shaw has become a full-time bench player. And the truth is that Chicago’s 2023 no. 1 draft pick should be playing every day—or traded for someone who can contribute in a more meaningful way.
Alcantara is also 24, but he’s coming along at a slower pace than Shaw. Still, the outfield prospect is extremely toolsy and would be a great gamble of a pickup, especially as a secondary acquisition in a trade.
For the Cubs, a deal like this makes sense because of the team’s dire need for starting pitching, not only for the rest of this season, but also for next year and beyond. Matthew Boyd, Shota Imanaga, and Jameson Taillon could all be free agents at the end of this season and Cade Horton will miss a good portion of next season recovering from April’s Tommy John surgery. The Cubs will need some healthy arms to replace them and Wacha, even at 35 years of age, fits that bill perfectly.
But is this a trade the Cubs would make? The team isn’t exactly known for its boldness when it comes to trade deadline deals. But getting a solid two-time All-Star starting pitcher for a pennant race and, potentially, two years after that is not something that comes along very often.
The post Chicago Cubs trade overpay for 2-time All-Star eyed by former MLB exec appeared first on ChiCitySports.