As home schedule concludes, the Cubs’ Wrigley Field career of Jon Lester may do the same

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CHICAGO, ILLINOIS – SEPTEMBER 16: Jon Lester #34 of the Chicago Cubs throws a pitch during the second inning of a game against the Cleveland Indians at Wrigley Field on September 16, 2020 in Chicago, Illinois. (Photo by Nuccio DiNuzzo/Getty Images)

CHICAGO – A great debate to have when it comes to sports here in the Windy City is to ask who is the greatest free agent signing of all time.

Fans of different sports and teams have their own picks, and one of those includes a current member of the Chicago Cubs.

Jon Lester was signed to a six-year, $155 million contract by the Cubs in December of 2014 and represented the team’s first step towards competition in the Theo Epstein era. In the previous three years, the club was only trading for future value, and the signing of the left-handed veteran showed they were here to win now.

It’s hard to believe that was six years, four playoff appearances, and a World Series championship ago, but here was Lester this past week taking the mound for what could be his last game at Wrigley Field.

That initial contract expires at the end of this season with a $25 million vesting option for the 2021 season. The Cubs may not end up picking that up with a salary bind coming up next spring, and Lester could choose to leave on his own as well.

So taking the mound for the game against the Indians on Wednesday, barring at Wild Card round start, will be the last time on the mound for the five-time All-Star. Don’t think Lester didn’t know that as he pitched under the lights against a Cleveland team he started a World Series game against the same venue four years earlier.

“You don’t know what the future holds so a lot emotions going into tonight,” said Lester. “Trying to make tonight go well.”

He went five innings allowing two earned runs with a strikeout and a walk, taking a no-decision in what would end up being a Cubs’ 3-2 ten inning victory. If this is the end, there isn’t disappointment in the journey for Lester, who helped the team transition into a contender while also making a pair of All-Star Games and finishing top three for the Cy Young Award in 2016.

But the finish might be a bit lacking, since the start came in an empty stadium in a 60-game season – one scenario he couldn’t have seen coming back in 2014 when he signed that six-year deal. It’s similar to what happened in Boston, when Lester’s nine year tenure with the Red Sox ended with his mid-season trade to Oakland.

There wasn’t the proper goodbye for the pitcher back then, and despite being home for this potential final game, it wasn’t quite the same.

“Going back to ’14, I didn’t really get to walk off the field like I wanted to at Fenway. Obviously tonight didn’t quite go the way I wanted to have an empty stadium,” said Lester. “Not how I really envisioned possibly my last start here.

“I’m not gonna say ‘Woe is me,’ but I didn’t think six years would go this fast.”

But what a six years it was, if indeed it came to an end at Wrigley Field on Wednesday night.

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