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(September 24, 2014 - Source: Jonathan Daniel/Getty Images North America)
(September 24, 2014 – Source: Jonathan Daniel/Getty Images North America)

For years, James Shields and Jon Lester dueled each other on the mound during their AL East days. On Tuesday, however, both will toe the rubber for different teams, trying to verify their current teams trading for them. Shields and Lester are tabbed as the starters for the Kansas City Royals and Oakland Athletics respectively when the two teams meet for the AL Wild Card game at Kauffman Stadium.

Shields, who compiled a 14-8 record for Kansas City this season, is in the final year of his contract with the Royals. He, along with Wade Davis and Patrick Leonard, was acquired in a trade with the Tampa Bay Rays, who received elite outfield prospect Wil Myers, infielder Elliot Johnson, and pitchers Jake Odorizzi and Mike Montgomery in return prior to the 2013 season.

It was no surprise that Lester was dealt at this year’s trade deadline, but what sent shock waves throughout baseball was who he was traded for. Oakland dealt outfielder Yoenis Cespedes for the southpaw, which left a void in Oakland’s lineup that was never filled. As a result, Oakland’s offense stumbled and they needed a loss by division rival Seattle to ensure the second wild card spot.

Both trades were very risky, as Kansas City, who didn’t seem close to contention, mortgaged a huge part of their future (Myers) for Shields. Cespedes provided a right-handed power bat for Oakland, who was left-handed heavy and also showed off his cannon arm on multiple occasions. The Athletics made an abundance of trades at the trade deadline and limped into the playoffs while Kansas City made the playoffs for the first time since 1985 when they won the World Series.

Lester and Shields have pitched several high-leverage games in their career. Both have started and won a World Series game. Shields won Tampa Bay’s lone game in their 2008 series loss to the Phillies. Lester, on the other hand, is 3-0 with a 0.43 ERA in three World Series starts, winning rings with Boston in 2007 and 2013. Both pitchers were born on the west coast and both pitchers started their careers in 2006.

Kansas City has faced its share of struggles over the past decade, but their crop of young talent and outstanding bullpen made Shields optimistic. He said, “I’ve only been here for two years, but when I got traded over here, I knew the magnitude of what this organization was headed for.” That organization, still led by the much scrutinized Ned Yost and Dayton Moore, is one of the final ten playing for baseball immortality.

Oakland general manager Billy Beane wasn’t shy about being aggressive at the trade deadline. Lester, who finished this season with a 2.46 ERA and 16 wins, was only part of the puzzle to end the A’s playoff struggles. Since Y2K, Oakland is only 1-7 in playoff series, losing to the Detroit Tigers in each of the past two seasons in the ALDS.

In terms of pitching against each other, Lester has the edge. His team sports a 5-1 record when he faces Shields head-to-head. Furthermore, Lester won three games against the Royals this season in less than a month. In an elimination game, statistics go out the window.

Since both are free agents at the end of this season and unlikely to re-sign with their respective teams, this match-up will determine which team’s gamble paid off. For Kansas City, their playoff drought is over and there are many bright years ahead. Oakland is trying to avoid another early postseason exit and more disappointment after making so many trades. Both teams have defied the odds with a smaller payroll and on Tuesday night, two former AL East rivals will face off one more time for a chance to face the Angels.

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