Worst: Astros sign Tony Sipp to a three-year, $18 million deal (Dec. 11, 2015)
In truth, this is the only candidate I could come up with for this distinction, as all of the other deals that didn’t work out were low-risk one-year pacts. That was not the case for Sipp, however, and the Astros ended up stuck with him.
Sipp put up an excellent 2015 season in Houston, pitching to a 1.99 ERA in 60 appearances. He’d put up a 3.38 ERA in 56 appearances the year prior, so he gave the club reason to feel confident in him. They were confident enough to give him $6 million a year for three years.
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The first two years of that deal were pure disasters. Sipp compiled a 4.95 ERA in 2016, seeing a huge spike in his hit and home run rates to the tune of a 1.603 WHIP. Most of his numbers were a little better in 2017, with one exception — his ERA rose to 5.79. He did not pitch at all in the postseason during the team’s championship run.
He was markedly better in 2018, pitching to a 1.86 ERA in 54 appearances. However, he’d already lost manager AJ Hinch‘s trust and was not used in many important or high-leverage situations. He made three appearances in the ALCS against Boston, allowing three of seven hitters to reach base.
So that deal was a bust, but it says a lot about a front office when the worst free agent contract you’ve given out is for a total of $18 million. You have teams like the Angels and Yankees who pay enormous sums to way-past-their-prime veterans, but the Astros have successfully avoided those albatrosses.