17. Arizona Diamondbacks
D-Backs owner Ken Kendrick has never been one to let desert money flow freely. The largest team payroll in history is just $131.6 million. That’s modest by contemporary standards and that was back in 2018. Kendrick only spent $90 million on talent last year and isn’t projected to break $100 million in 2023 either.
The one time, really the only time, Kendrick let the D-Backs run financially wild was over the winter of 2015-16 when he decided that the way to make up ground on the division rival Dodgers was to heist one of their ace pitchers.
A $206.5 million promise to Zack Greinke, the National League’s reigning ERA champion, payable over six seasons, accomplished that.
It was then and remains today the richest single payout in franchise history, both for raw dollar expense and (at $34.4 million) at AAV.
In due course, Kendrick regretted that moment of madness. So when Greinke won 55 of 84 decisions for an Arizona team that was swept out of its only postseason appearance, Kendrick swapped the costly star to Houston at the 2019 trade deadline.
The Greinke deal was completely out of character for Arizona, whose next richest free agent award, to Madison Bumgarner, registered only $85 million over five seasons. That’s less than half what they paid for Greinke.
More in character was the December 2018 trade that dispatched team star but free agent-to-be Paul Goldschmidt to St. Louis. There he signed a $144.5 million, six year contract — far less than the cost of Greinke — that runs through 2024.