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Come Fan with UsWednesday, August 5, 2026

Cubs will try to recruit players by not winning

Wednesday’s Say Hey, Baseball includes Joe Maddon’s free agent strategies, Justin Bour’s Rookie of the Year votes and the Indians’ outfield dilemma. Subscribe for your daily Say Hey!

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Well, it certainly is an unorthodox strategy. On the heels of Kris Bryant’s Rookie of the Year Award and Joe Maddon’s Manager of the Year Award, the Cubs are looking to attract big-name free agents to pad their roster for another postseason run in 2016. Rather than downplaying a century of bad luck, however, Maddon believes that the lack of championships will only enhance his sales pitch. According to the Cubs’ skipper, many players would jump at the chance to make history with the team.

The Cubs are positioned to be big spenders in the offseason, but they haven’t been linked to any major free agents thus far. Veteran utility player Ben Zobrist seems like an easy fit for the club, especially since he spent nine years under Maddon’s tutelage with the Rays. He’s past his prime, but can handle a variety of positions and fill in gaps where necessary. Right-hander Hisashi Iwakuma could also patch a hole in the Cubs’ rotation, though he has been injury-prone over the last two seasons and is facing decline. In order to avoid stockpiling veterans with short shelf lives, the Cubs will need to consider swapping some of their young hitting talent for equally young pitching depth.

No matter which route Maddon and the Cubs take, they have two things working to their advantage: time, and a 97-win record. Free agents may be attracted by the idea of being the first to bring a championship to Chicago in 107 years, but only because the Cubs are actively positioning themselves to compete for another postseason berth in 2016. Of course, the outfield petting zoo and onesie road trips don’t hurt, either.

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