Jon Lester Reflects on Possible Final Home Start as a Cub: 'I Didn't Think Six Years Would Go This Fast'

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Wednesday night might have been Jon Lester’s last start as a Cub in Wrigley Field.

It hit home. It also made him remember those final days as a member of the Red Sox in July 2014.

"That's the most frustrating part," Lester said after giving up two runs over five innings against the Indians. "Going back to 2014, I didn't get to walk off the field like I wanted to at Fenway. Having an empty stadium [is] not how I envisioned my last start here."

When Lester made his final Fenway Park start as a Red Sox on July 20, 2014 -- throwing eight scoreless innings -- there was still uncertainty regarding the pitcher's future in Boston. He would make one more start with the Sox, tossing six innings at Tropicana Field, before being dealt to Oakland.

While the lefty will likely pitch in the postseason, the chance to pitch in Wrigley remains in doubt because of the way the schedule is slated to be set up.

"I didn't think six years would go this fast," he said.

After 2020 Lester is likely headed to free agency, with the Cubs carrying a $25 million option on the 36-year-old. In 10 starts this season he owns a 4.91 ERA.

In early May, Lester suggested to WEEI.com he would be open to a reunion with the Red Sox.

"Obviously everything is open. I'm open-minded to anything," he said. "Absolutely it would be cool to go back and finish my career where it all started."

Lester is 76-43 with the Cubs, earning two All-Star nods and finishing in the top ten in Cy Young voting twice. In his career at Wrigley Field, he's compiled 40 wins -- second to his 51-win total at Fenway Park -- to only 24 losses (via Baseball Reference).

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