Part 1/9:

The Worst Free Agent Contracts Since 2000

Every offseason in Major League Baseball brings a wave of new contracts, but not all are created equally. Some deals leave fans and analysts alike scratching their heads and asking, "What were they thinking?" In this article, we take a look at the worst free agent contracts handed out each year from 2000 to 2024.

2024 Offseason: Jordan Montgomery

The 2024 offseason has barely begun, but one contract stands out: Jordan Montgomery’s one-year, $25 million deal with an option for a second year. Montgomery, who was among the worst pitchers in baseball last season with a 6.23 ERA and negative WAR, represents a significant risk for the Diamondbacks as they deal with his now two-year, $47.5 million contract.