Baltimore Orioles: The worst contracts since 2010

The Baltimore Orioles had a good run before the organization started a complete rebuild in 2018. Not signing these players could’ve put them over the top.

The Baltimore Orioles had a good run before the wheels fell off the wagon and the organization started a complete rebuild in 2018. They reached the postseason in 2012, 2014, and 2016 but could never get over the hump and bring home a World Series.

While former Orioles general manager Dan Duquette deserves some credit for bringing in bargain players like Nelson Cruz and Delmon Young, he also had more than his fair share of free agent duds.

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So what could Duquette have done better to help Baltimore bring home its fourth World Series title during its championship window?

Not signing these terrible contracts over his eight years with the team would’ve helped quite a bit.

3. Alex Cobb: 4-year, $57M

The truth is the worst and second-worst contracts that Duquette signed players to over his eight years with the club are pretty straight forward. The rest is debatable as to which one is the worst.

Yovani Gallardo and Mark Trumbo get honorable mentions on our duds for deals list, but Alex Cobb’s deal just turned out a notch worse (so far).

Prior to the 2016 season, in which Cobb underwent Tommy John surgery, his numbers were phenomenal. In 2013 and 2014 Cobb had an ERA under 3 and was a solid rotation arm.

Of course, Tommy John surgery is known to derail pitcher’s careers and it certainly has been that way for Cobb.

He came back for the Tampa Bay Rays in 2017 and had a solid year posting a 3.66 ERA in the tough AL East. That’s when the O’s swooped in a signed him to a 4 year 57 million dollar deal.

Since signing with the Orioles, injures have really derailed Cobb’s career. He pitched in 2018, but not well, posting a 4.9 ERA. Then 2019 was mostly a wash, only pitching in 3 games and posting an ERA just south of 11.

2020 was poised to be a potential rebound year for Cobb, but with the season on hold and a good chance that it might get canceled, the first three years of the contract seem to be a waste. And for $57M that’s an awful deal.

Baltimore Orioles: The worst contracts since 2010

2. Ubaldo Jimenez: 4-years, $50M

Signed in 2014, the Baltimore Orioles were looking to bolster their starting rotation and were finally willing to spend the money to do it. They doled out a massive four year $50M contract to bring in Ubaldo Jimenez, and since he was tagged with a compensatory pick the Orioles also gave up their first-round pick, which was the 17th overall pick in the draft.

It was the longest contract that the Orioles had ever signed a free agent pitcher.

When Jimenez signed the hype was there, but so were the warning flags. He pitched phenomenally the second half of the prior year – posting a 1.82 ERA in his final 13 games. But in the 19 before that, he pitched to a 4.56 ERA, and in the three years prior he never had an ERA lower than 4.68.

It was the classic situation for a one year prove it type of deal. But instead, Duquette opened up the pocketbook and got burned.

Over his four years with the Orioles, Jimenez posted a whopping 5.22 ERA and is the reason many O’s fans have PTSD flashbacks when watching wildcard games.

Of course, Jimenez never should’ve been in that game against the Toronto Blue Jays in 2016, but giving up a three-run shot in the bottom of the 11th inning to end your team’s season is a nightmare for even the best players to move on from.

Jimenez wasn’t anywhere near the best and was plagued with inconsistency throughout his career. Trying to bounce back in 2017 Jimenez had the worst year of his career posting a 6.81 ERA in 142.2 innings. By the time his contract expired at the end of the season, Orioles fans were glad to see him go.