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5 moves that led to Terry Ryan's dismissal

Dylan Buell / Getty Images Sport / Getty

Regardless of how the Terry Ryan era ended, he'll go down as one of the most important figures in Minnesota Twins history. Ryan oversaw the team's on-field recovery as rumors of contraction surrounded the team during his first stint as general manager, turning the club into a model small-market organization.

His second turn as GM, which ended with his firing on Monday, didn't go nearly as well. Though it could be seen as surprising only because he's been with the Twins since 1972, Ryan sealed his fate by making several puzzling moves and signing some bizarre contracts over the past few years that have helped turn the team into one of baseball's worst.

Here's a look at five of Ryan's worst moves that led to his dismissal.

2012: Traded Denard Span to Nationals for Alex Meyer

Ironically, Span was drafted by Ryan during his first stint as GM in 2002, and he turned into a solid leadoff hitter who was dynamite in two Twins postseason appearances. Ten years later, after posting a .283/.342/.395 line and accumulating 3.4 WAR in 2012, Ryan dealt him away to Washington for pitching prospect Alex Meyer. Despite a bit of injury trouble, Span became an important part of the Nationals for three years before joining the Giants this past winter. What's Meyer up to? Well, he's on the disabled list in Triple-A with shoulder issues and owns a 14.21 ERA in four big-league appearances.

2013: Signs Ricky Nolasco to a 4-year, $49M contract

When he signed this contract, Nolasco had a 4.37 career ERA and was approaching his 31st birthday. Since signing this contract, Nolasco's turned 33, has not posted a single-season ERA below 5.22, and has allowed over 11 hits per nine innings as a Twin. He made just nine appearances and eight starts in 2015 thanks to an ankle injury that sidelined him from June through September, finishing the year with a 6.75 ERA. Fortunately for the Twins, that $13-million club option for 2018 Ryan stuck onto the end of this deal can - and almost assuredly will - be bought out for just $1 million.

2014: Signs Ervin Santana to a 4-year, $54M contract

Ryan signed Santana to the biggest free-agent contract in Twins history, only to see him test positive for the performance-enhancing drug Stanozolol three days before the season opener. The Twins probably wish he stayed suspended, as he owns a 4.06 ERA and 1.299 WHIP over 34 starts for the club while his strikeout rate has decreased significantly. Oh yeah, the Twins had to give the 28th pick in the 2015 draft to the Braves as compensation for signing Santana. Mike Soroka - the right-hander selected with the pick - is now the Braves' No. 11 prospect, according to MLB Pipeline.

2014: Signs Phil Hughes to a 5-year, $58M extension

Ryan gave Hughes a somewhat reasonable $24 million over three years as a free agent in December 2013, and the former Yankees prospect gave them an outstanding 2014 campaign, posting the best strikeout-to-walk ratio (11.625) in baseball history and finishing seventh in Cy Young voting. That prompted Ryan to tear up the last two years of his original deal and hand Hughes a fresh five-year, $58-million contract over the winter. His K-BB ratio in 2015 plummeted to 5.88, and his 29 home runs allowed led the AL. This year's 5.95 ERA and 2.62 K-BB ratio bumped him into the bullpen before he was diagnosed with thoracic outlet syndrome in June, ending his season.

2015: Traded prospects Chih-Wei Hu and Alexis Tapia to Rays for Kevin Jepsen

With the Twins surprisingly hanging around the wild-card race, Ryan snagged Jepsen at last year's deadline to give the bullpen some help. He performed well down the stretch, owning a 1.61 ERA and 10 saves over those two months, but was completely ineffective this year, losing his closer's job and ultimately being released earlier this month. Meanwhile, MLB Pipeline now lists Hu, the Taiwanese pitcher, as the Rays' No. 12 prospect, while Jepsen almost immediately returned to the Rays and is back in their bullpen - meaning Ryan traded a top-30 prospect for literally nothing.

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