Red Sox: The five biggest moments of Jon Lester’s career in Boston

BOSTON, MA - JULY 20: Jon Lester #31 of the Boston Red Sox reacts after walking a man in the sixth inning against the Kansas City Royals at Fenway Park on July 20, 2014 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)
BOSTON, MA - JULY 20: Jon Lester #31 of the Boston Red Sox reacts after walking a man in the sixth inning against the Kansas City Royals at Fenway Park on July 20, 2014 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images) /
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Red Sox Jon Lester
BOSTON, MA – MAY 3: Jon Lester #31 of the Boston Red Sox makes the assist on a ball hit back to the mound by Coco Crisp #4 of the Oakland Athletics in the sixth inning at Fenway Park on May 3, 2014 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images) /

Jon Lester sets a career-high in his final season with the Red Sox

It’s May in 2014, just a few years after his no-hitter in that very month and just months removed from winning his second World Series ring. Jon Lester is on the mound against Oakland and it’s a beautiful day at Fenway Park.

None of us knew that he would soon be playing for these very Athletics in a few short months but on this day, he made them regret coming to Boston.

Jon took the ball this afternoon and seemingly never gave it back. He would give the Red Sox eight strong innings of work and at the end of the day, he’d be walking away with a career-high 15 strikeouts. While his career took him to several other teams where he also achieved great things, this mark still stands for the lefty.

It was no secret that Lester wanted to remain with the Red Sox and finish out his career in Boston, but the owners took his kindness too far. John Henry and the fellas lowballed the lefty with a disgusting four-year.$70M contract offer that was never going to fly.

Then they came up with the great idea to trade him to Oakland as Boston’s season was declining with the hopes of bringing him back in free agency that winter. Yeah, because that always goes well, idiots.

He never should’ve been traded and the Red Sox let one of their few homegrown pitching talents get away without even putting up a fight. I do find it a bit romantic that he would set a career mark against a team that he would be fighting for in just two months’ time. Lester’s efforts were almost ruined as Chris Capuano served up three runs to the A’s in the top of the ninth before Koji Uehara came in and slammed the door shut.

Jon Lester was one hell of a pitcher and one hell of a person from everything you’ll see, hear and read. Whether it be from his coaches, teammates, or those he’s helped in his communities, he’s earned and deserved all the goodwill he receives. Not only was he a giant on the field but off of it as well.

After 16 years of stellar baseball, I think he can walk away with his head high. I can’t wait for his name to show up on the ballot in a few years and we can praise him all over again.

The pitch that will keep Tanner Houck in the rotation. dark. Next