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8) Tony Sipp-3 years, $18 million
Tony Sipp was a revelation in the 2015 season, posting a microscopic 1.99 ERA. The Astros rewarded him with a three-year, $18 million deal.
The results of said deal were…not great. Sipp posted a 4.95 ERA with a 1.6 WHIP in the 2016 season. The 2017 season was even worse for Sipp, with his ERA ballooning to 5.79. Though he regained form in 2018, that is not enough to offset his abysmal first two years.
Sipp played one more year in 2019 with the Washington Nationals.