2. The Anthony Rizzo trade
While the Bryant trade looks like a success at this point, the Anthony Rizzo trade just seems like a stab in the back. If there was ever a guy to make a lifelong Cub, it was Rizzo. He played gold-glove defense at first base, drove in around 100 runs per year, hit for power, and was an unparalleled clubhouse presence. He was the leader of the Chicago Cubs for years and it would have made all the sense in the world to keep him long-term.
Even though the main return for Rizzo was Kevin Alcantara, who has risen to become the Cubs' number 4 prospect, it was not worth it. The other prospect in the deal was pitcher Alexander Vizcaino, who is no longer in the organization and hasn't thrown a pitch in a professional game since 2021. The other main component of this trade looking like a complete failure is the fact that the Cubs have been lacking not only a first baseman but a slugging left-handed batter since this deal.
Trey Mancini and Eric Hosmer were laughable answers to the first base problem going into the year while Matt Mervis' first stint in the big leagues was ugly. There's still time for Mervis to flip the script, but giving Rizzo a contract extension in 2021 would have saved a lot of time and tinkering at first base and kept stability in the lineup that it desperately needs. Overall, trading Rizzo away seemed like a mistake when it happened and it looks even worse now.
Yankees get: 1B Anthony Rizzo
Cubs get: OF Kevin Alcantara and RHP Alexander Vizcaino