Impetus: the Chicago Cubs release Jason Heyward after seven years of his eight-year contract
Between 2008 and 2009, Jason Heyward was one of the most hyped prospects in baseball. After the 2009 season, he was the de facto #1 prospect in baseball. In the Spring Training of 2010, Heyward emerged onto the radar of the national spotlight when he clubbed a home run so far, it left the ballpark and shattered the windshield of a car in the parking lot.
He was so good, he forced the Atlanta Braves to put him on the Opening Day roster instead of taking part in the traditional practice of stashing him in the minors for two months in order to ensure that they can keep him for an additional year of indentured servitude known as team control, instead of getting to free agency.
That Opening Day, Jason Heyward took the first step to immortality by launching a three-run home run in his very first at-bat.
To this day, I still consider that day and that moment, one of the most magical sports memories I’ve ever had.
He performed so well through the first few years of his career, it became very apparent that he was going to become problematic in the sense that as he grew closer and closer to free agency, he was going to command a tremendous amount of money, and as any Braves fan can explain, the Braves absolutely do not like to spend money.
The inevitable became fulfilled when the Braves shipped him off to St. Louis for his contract year in exchange for a pitcher who still had team control available to him, and Heyward unsurprisingly put up a monster year for the Cardinals. He went into free agency in as optimal position as a player really could be in.
And the Chicago Cubs came knocking, as they signed him to an 8-year, $184 million contract. Jason Heyward had accomplished what just about every professional athlete strives to do; make it to the big leagues and perform well enough to where you can make it to free agency and cash in on a monster megadeal.
But then something interesting happened: Jason Heyward basically forgot how to play baseball. From the moment he suited up for the Cubs, he was mostly an offensive liability, hitting .245 and OPSing .700 between 2016 and 2022. Almost all of his value came from the fact that he was still a reliable glove in the outfield, winning two Gold Glove awards. That, and the fact that as a person, Jason Heyward has always been a pretty outstanding human being, personable, polite, philanthropic, and just a great teammate, as many of his peers have attested.
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