Astros: Best, worst free agent signings of past decade

HOUSTON, TX - OCTOBER 17: Charlie Morton #50 of the Houston Astros pitches in the first inning against the Boston Red Sox during Game Four of the American League Championship Series at Minute Maid Park on October 17, 2018 in Houston, Texas. (Photo by Bob Levey/Getty Images)
HOUSTON, TX - OCTOBER 17: Charlie Morton #50 of the Houston Astros pitches in the first inning against the Boston Red Sox during Game Four of the American League Championship Series at Minute Maid Park on October 17, 2018 in Houston, Texas. (Photo by Bob Levey/Getty Images) /
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BOSTON, MA – OCTOBER 14: Tony Sipp #29 of the Houston Astros delivers the pitch during the eighth inning against the Boston Red Sox in Game Two of the American League Championship Series at Fenway Park on October 14, 2018 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)
BOSTON, MA – OCTOBER 14: Tony Sipp #29 of the Houston Astros delivers the pitch during the eighth inning against the Boston Red Sox in Game Two of the American League Championship Series at Fenway Park on October 14, 2018 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images) /

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.

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