Texas Rangers: Jacob deGrom
Where Mike Trout may be the best position player of this generation only to have injuries cut his resume short, Jacob deGrom is the pitching version of him. deGrom was one of the most dominant pitchers on one of the biggest stages in baseball, playing for the New York Mets. He won back-to-back Cy Young awards, with three straight seasons of 200+ innings pitched. He regularly had an ERA in the low 2.00s and topped the 200-strikeout mark in four of his first six years.
After the COVID-shortened 2020 season, things really started to unravel for the former Stetson Hatter. It looked like deGrom was on pace for one of his best seasons yet in 2021, but he dealt with right side tightness and after a short IL stint. After an attempt to make it back with the Mets, he ended up out for the year with forearm tightness, throwing just 92 innings. This lingered into his 2022 season where he didn't debut until August, showcasing for his upcoming free agency. He threw just 64 1/3 innings but looked like his normal self.
After all of that, the Rangers gave the righty a five-year deal worth a whopping $185 million. In the first two years of that deal, granted the Rangers won a World Series that deGrom was not a part of, deGrom has thrown just 41 innings and has made $$70 million. Hopefully we see deGrom get healthy, but the Rangers might be regretting the fact that they're still on the hook for another $115 million over the next three years.