The Orioles frustratingly waited until the end of the 2014 off-season before adding Ubaldo Jimenez and Nelson Cruz, the latter of whom helped lead the Orioles to their first Division crown since 1997.

The Baltimore Orioles entered the 2013-14 MLB off-season with a sour taste in their mouth. Yes, they finished the 2013 season with an 85-77 record, good for a second consecutive winning season.

But winning seasons were no longer good enough for a team that, in 2012, had tasted postseason magic for the first time since 1997, and entered 2013 expecting to reach the postseason again.

The core of Adam Jones, Chris Davis, Manny Machado, Matt Wieters, Nick Markakis and JJ Hardy returned, but the Orioles somehow finished in fourth place in the AL East.

Their shopping list entering the off-season included adding a top of the rotation starter, a power bat, and an upgrade at closer.

So it was frustrating for Orioles fans when the front office entered the off-season seemingly sleepwalking.

Big offensive threats Robinson Cano and Josh Hamilton signed with the Mariners and Angels, respectively, while ace Zack Greinke signed with the Diamondbacks.

(Sound familiar?) Even when it seemed like the Orioles had agreed to add closer Grant Balfour on a multi-year deal from Oakland, Balfour wound up failing his physical and his deal to Baltimore was scrapped.

In fact, their lone deal in the first half of the off-season was trading incumbent closer Jim Johnson to the Athletics for light-hitting utility player Jemile Weeks, who wound up playing sparingly in Baltimore.

While the Orioles seemingly sat on their hands, their biggest rival, the Yankees, loaded up, signing Japanese ace Masahiro Tanaka, star center fielder Jacoby Ellsbury, power hitter Carlos Beltran, and even former Oriole Brian Roberts.

It took a while for the Orioles’ 2013-2014 off-season to come together, but it paid off big in the end

On December 18, 2013, the Orioles made a minor trade aimed at upgrading their outfield defense, acquiring David Lough from the Royals in exchange for veteran DH Danny Valencia. Lough came in as the presumptive left fielder and replacement for Nate McLouth, who had signed with the Nationals.

But Lough’s light bat did little to excite Birdland, as he posted a .694 OPS in 2014 and was designated for assignment in 2015 after posting an OPS in the .500s.

Orioles fans waited for the team to make a splash. Days turned to weeks, and weeks turned to months as spring training neared.

At the same time, an interesting phenomenon regarding free agency was occurring: teams were reluctant to sign certain solid but unspectacular free agents, because doing so would involve giving up a pick in the June 2014 draft.

By February 2014, two big-name free agents remained on the market: starting pitcher Ubaldo Jimenez and power hitter Nelson Cruz.

And out of nowhere, the Orioles struck.

The Orioles signed Jimenez, who was coming off a fantastic season with Cleveland, to a four year, $50 million contract, marking the highest contract the Orioles had ever given to a pitcher.

Having already sacrificed their draft pick to sign Jimenez, the Orioles doubled down and signed Cruz to a one year, $8 million deal. An extended stretch of nothing suddenly turned into a very productive off-season for the Orioles.

The Orioles had a surprisingly successful off-season in 2013-2014, adding power hitter Nelson Cruz and star pitcher Ubaldo Jimenez

While Jimenez struggled over four seasons in Baltimore (including giving up the infamous walk-off home run to Edwin Encarnacion in the 2016 AL Wild Card Game), Nelson Cruz wound up being one of the Orioles’ best free agent signings in history.

Cruz posted an .859 OPS, mashed 40 home runs and drove in 108 runs, good for terrific 4.7 WAR. Cruz also provided the Orioles’ entire offense – a two run home run – in their 2-1 series-clinching win in Detroit, marking their last playoff win to date.

Behind Cruz, Jones, Markakis, and emerging stud closer Zack Britton, the Orioles easily won the American League East in 2014 and swept the Tigers in the ALDS, reaching their first LCS since 1997.

While the Orioles’ 2014 season ended abruptly at the hands of the Kansas City Royals, there was no denying that the 2014 season was special.

And after waiting, and waiting, and waiting some more, the Orioles made a free-agent splash to cap a surprisingly successful offseason.