3 decisions that may haunt the Cubs for years to come

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Cubs: 3 haunting decisions – #2: Sending Anthony Rizzo to the Yankees

Perhaps one of the most heart-wrenching trades in Cubs history took place ahead of the 2021 trade deadline, when the team sent Anthony Rizzo to the Bronx. After extension negotiations went nowhere, the Cubs cut their losses and attempted to recoup some value from their longtime first baseman, rather than let him walk for nothing at season’s end.

Fast forward to the end of 2022 and Rizzo went on to have a resurgent year in the power department at the plate. Though the batting average was down to .218 in 2022, Rizzo launched 32 long balls, the most he’s hit since 2017. Adding in his consistent Gold Glove-caliber defense and the Cubs’ struggles to find an heir at first, and it’s not hard to see why he’s been missed.

In return, the Cubs landed Kevin Alcantara, who is a top 100 prospect in his own right. Yes, on paper, a top 100 prospect for Rizzo at the time was a phenomenal return. Along with Alcantara however, Alexander Vizcaino was sent to the Cubs – and he’s been a huge disappointment. He essentially did not show up to play baseball in 2022 and spent the entire season on the restricted list. It seems the trade is now essentially Alcantara for Rizzo straight up. Which, OK, but there’s more.

Alcantara’s emergence in the farm is not what will haunt the Cubs. The fact that Rizzo was a rental and could have been brought back to Chicago in the offseason last winter is where Chicago’s front office misfired. They had a chance to completely fleece the Yankees by acquiring a top 100 prospect while also bringing Rizzo back in free agency but decided to part ways instead. He will haunt the Cubs as long as he’s still producing and he clearly has plenty left in the tank. His 32 home runs this season would have led all Cubs hitters.