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5 moves that led to Cherington's exit from Red Sox

Greg M. Cooper / USA TODAY Sports

Flags may fly forever, but one of the architects of the eighth World Series championship in Boston Red Sox history is out the door.

Owner John Henry was only going to tolerate last place for so long, as the flame of general manager Ben Cherington's torch - handed down from Theo Epstein - was extinguished in another seismic August shift at Fenway Park.

The good faith Cherington earned with a surprise 2013 title and a well-stocked farm system had run out, and although new president Dave Dombrowski lobbied for Cherington to remain with the team, the writing on the wall was clear after plenty of recent swings and misses.

Signing the dynamic duo

There was a sense of desperation when Cherington signed Pablo Sandoval and Hanley Ramirez for a combined $188 million in late November. While both were superstars with their respective California clubs, they represented questionable decisions for the Red Sox, in what appeared to be a knee-jerk reaction to 2014's last-place finish. The short-sighted belief that Ramirez would transition into an outfielder has proven disastrously wrong, while Sandoval's already declining at the plate and defensively.

Losing Lester

Arrogance cost the Red Sox the ace they so desperately need when they gambled on Jon Lester last season and didn't sign him to an extension. The left-hander was brought through the system in Boston, won in Boston, and wanted to stay in Boston. Cherington and the front office undervalued him, traded him away, and then tried their best to desperately lure him back. Lester went on to sign with the Chicago Cubs and owns a 3.21 ERA across 23 starts.

Cardinal error

Sending John Lackey to the St. Louis Cardinals at the 2014 non-waiver trade deadline for Joe Kelly and Allen Craig was once considered a complete steal for the Red Sox. Now, it's viewed as one of the most lopsided losses in Cherington's tenure. Both Kelly and Craig have struggled mightily in Boston, both spending time in Triple-A. Craig has hit .130/.235/.192 in 53 games while Kelly owns a 5.09 ERA across 29 starts in Boston. Lackey, on the other hand, owns a career-best 2.87 ERA in 159 2/3 innings this season while making the league minimum.

Unproductive Porcello

Before Rick Porcello even threw a pitch in Boston, Cherington handed the 26-year-old a four-year, $82.5-million extension. The right-hander responded by going 5-11 with a career-worst 5.81 ERA across 20 starts. Porcello would have been eligible for free agency at the end of the season and said that he didn't want to negotiate during the season.

Castillo cashes in

After just missing out on Jose Abreu, the Red Sox opened their wallets and handed Cuban outfielder Rusney Castillo a seven-year, $72.5-million deal last August. Castillo's transition has been slowed by inconsistency and injury, and while he's shown flashes of why he was so highly coveted, he finds himself platooned in right field with Jackie Bradley Jr. as Ramirez starts in left.

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