5 - Paul Goldschmidt
While many of these extensions involve buying out the prime years of young players, the case for extending Paul Goldschmidt is much different. After an electric 2022 MVP season, Goldschmidt took a few steps back in 2023. He wasn't anywhere near MVP level, but he was still a solid above-average hitter for the Cardinals at first base. However, the warning signs for his aging and regression definitely showed. His OPS dropped from .981 to .810 and his OPS+ from 177 to 121. His numbers were still very respectable, but there's no question his decline has begun.
However, Goldy's talents at first base will be extremely difficult to replace. Alec Burleson's offensive ability still hasn't developed as well as the Cardinals would like, and it's unlikely St. Louis will restrict super-utility defender Brendan Donovan to first base. Also, Jordan Walker will most certainly not be seeing any innings at first in the foreseeable future.
With only one year left on his current contract, the Cardinals are faced with a choice of either extending Goldschmidt or trading him. It's unlikely they allow such a key player to walk in free agency, and trading him to recoup value is also not happening. Mozeliak and the front office have made it clear they intend to keep both Arenado and Goldschmidt in an attempt to compete next year. Trading Goldschmidt would be walking back on that promise, and also likely force Nolan Arenado out of St. Louis (in a similar fashion to his exit from Colorado).
Goldy would also likely return on a team-friendly deal. He's expressed his love for St. Louis on numerous occasions, and his current contract extension was also a bargain for the Cardinals. If the price is right, extending Goldschmidt is a no-brainer. Championship teams always have steady veteran leadership, and his intangibles and leadership in the clubhouse as an experienced star are also extremely valuable.