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Orioles’ choice of Ubaldo over Santana proves to be a glaring mistake

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What could have been had the Orioles signed Ervin Santana in 2014 instead of Ubaldo Jimenez?

MLB: Minnesota Twins at Baltimore Orioles Evan Habeeb-USA TODAY Sports

It was a rainy evening game at Camden Yards on Tuesday, but Oriole fans felt like they had the sun in their eyes from the glaring mistake watching Ervin “Magic” Santana’s sizzling 2-0 victory over the Birds.

The Twins’ right-hander masterfully pitched a complete game, two-hit shutout the very next day after Ubaldo Jimenez blew a 5-0 lead in the first game of the three-game sweep by Minnesota.

Anyone who remembers the 2014 Orioles’ offseason was reminded of how the team erred on February 19 of that year when the Orioles chose to sign Jimenez instead of Santana when both were seeking contracts as free agents.

The Orioles were looking to add one or two starting pitchers that year, and Dan Duquette’s style of waiting out the free agent market seemed to be working in his favor. Both Santana and Jimenez surprisingly remained unsigned and available even after spring training had begun.

Early offseason projections indicated that both pitchers would be in-demand targets in free agency. Bleacher Report placed Jimenez in the seventh slot of its top 15 free agent list and projected he would receive a five-year, $75 million deal. Santana was number three with a five-year, $95 million forecast.

Although Jimenez had struggled since his sensational 2010 season with the Rockies when he finished third in the Cy Young voting, he seemed to have rebounded in 2013 with Cleveland.

He finished that season with a 13-9 record and a 3.30 ERA. Much was made of how well he pitched in the second half after posting a 4.56 ERA in the first, boosting the impression that he indeed found his way again. And he had a super strong finish, going 4-0 with a 1.09 ERA in six September starts.

Santana and Jimenez shared comparable career numbers at the time. Ubaldo was 82-75, with a 3.92 ERA and 1.345 WHIP. Santana was 105-90, 4.19 ERA and a 1.281 WHIP. Santana, also, was coming off of a strong year with Kansas City pitching to a 3.24 ERA and 1.142 WHIP.

The Orioles had hoped to sign Monkton native A.J. Burnett, 37 at the time, to a short-term deal that would be a much more typical pitcher signing for the Orioles. But Burnett made it known that he wanted to return to the Pirates, and Jimenez – along with Santana – became prime targets if the price was right.

With the free agent market developing slowly and January quickly became February, Santana’s and Jimenez’s agents started to drop their asking price. The Orioles brass seemed to be in the driver’s seat, approaching a fork in the road. Hindsight shows they chose the one that should have been much less traveled.

Believing that the Red Sox and the Blue Jays were getting closer to a deal with Jimenez, the Orioles thought they needed to guarantee a fourth year to lock him in. They signed Jimenez to a four-year, $50 million deal – the longest contract the Orioles had ever given to a pitcher from outside the organization. (The team extended Scott Erickson five years in 1999.)

A lot of money for the Orioles but a bargain compared to what was initially expected.

What coulda, shoulda, woulda been had the Birds made a different choice? Santana’s shutout Tuesday lowered his ERA to 1.80 and improved his record to 7-2. Ubaldo’s Monday numbers were as horrendous as Santana’s were brilliant. He surrendered nine hits and six runs in just four innings, raising his ERA to 7.17 and his OPS allowed to .906.

In that offseason prior to the 2014 campaign, Santana remained unsigned for nearly a month after Jimenez’s deal. His demands continued to plummet. There was even speculation that the Orioles were in still in the hunt. Could they end up signing both Santana and Jimenez? After all they signed Nelson Cruz to a one-year deal five days after inking Ubaldo.

Maybe they could have, but they didn’t. Santana signed a one-year, $14.1 million deal with the Braves, followed by a four-year, $55 million contract with Minnesota the next year. Initially, the Twins’ deal didn’t look too good when Santana was suspended for 80 games for a positive PED test the first week of the deal in 2015.

But Santana came back to perform exceptionally well, especially this year when the Orioles would love to have him in the rotation instead of Jimenez.

The numbers below for both pitchers since that fateful 2014 year show how Santana’s performance has totally eclipsed Jimenez’s. They are a shining example of what a big mistake the Ubaldo signing was. You might want to put on some shades first:

Santana: 35-28, 3.50 ERA, 1.215 WHIP

Jimenez: 27-33, 4.93 ERA. 1.487 WHIP