7. Swinging and missing on an Oscar Taveras replacement over and over again
The death of Oscar Taveras was a huge tragedy and a massive blow to the Cardinals' long-term plans. No, most organizations don't have to deal with something as horrible as this, but how the Cardinals failed to rebound for years accelerated many of their issues as an organization.
Taveras passed away in October of 2014, and while he was a part of their fourth straight trip to the NLCS, he was expected to become the star middle-of-the-order bat to propel them through the rest of the 2010s and into the 2020s in the seasons that followed. In response to the tragedy, Mozeliak went out and made an aggressive move, one that would spark a chain of huge swings that failed time and time again.
First, Mozeliak traded a package headlined by dynamic starter Shelby Miller for Jason Heyward, who, although he had a great season for the Cardinals in 2015, would sign with their rival, the Chicago Cubs, the following offseason.
After the Cardinals regressed in 2016 and the Cubs went on to win the World Series, the Cardinals snatched outfielder Dexter Fowler from them in free agency, thinking they had solved their outfield woes, but instead grabbed a terrible contract for their books.
After the 2017 season, the Cardinals got really aggressive, first agreeing to a trade for reigning NL MVP Giancarlo Stanton before he vetoed the deal, but then turned around and sent Sandy Alcantara and Zac Gallen to the Miami Marlins for Marcell Ozuna.
After that mess, the Cardinals decided to pass on Bryce Harper, believing their investment in Fowler and young outfielders that were on the way would be the answer to their woes, but once again, those things did not pan out.
Sure, the Cardinals got their stars in 2019 and 2021 by trading for Paul Goldschmidt and Nolan Arenado, but it came after years and years of failing to replace Taveras both internally and externally. This left plenty of money wasted and young talent sent elsewhere, hurting the Cardinals' long-term outlook in a major way.
The fact that Mozeliak still points to Taveras' death as an issue for the club shows you how deeply it impacted their decision-making for so long. Again, it was a major tragedy, but just how much Mozeliak put his eggs in that basket for the future of the organization was a major issue, and he followed it up with mistake after mistake that cost the Cardinals big time.