Cubs Insider

Jon Lester: Maybe Cubs-Red Sox symmetry of career ‘fate’

Cubs Insider
Lester with Cubs and Red Sox

Who says you can’t expect to pay for past performance in a free agent signing?

Well, other than Theo Epstein, Jed Hoyer and dozens of other major league sports executives.

Apparently no one told Jon Lester, because the former Cubs All-Star workhorse and World Series hero managed to pull off a unique career feat that would be the envy of any free agent — never mind the executive responsible for signing him — and that carries maybe a little extra resonance this week as the left-hander announces his retirement.

When the Cubs signed Lester to a six-year, $155 million contract seven years ago last month, he had a .636 winning percentage (110-63) and 3.64 ERA in nine years with his original team, the Red Sox.

His performance in six years with the Cubs: A .636 winning percentage (77-44) and 3.64 ERA.

“It’s crazy that the numbers ended up that way,” Lester said Wednesday during an appearance on the Cubs Talk Podcast (link below). “I don’t know if that’s just fate or what. But it’s pretty cool.”

Talk about consistency. The strangeness of the symmetry aside, Lester’s performance as a Cub in his 30s was emblematic of at least that much: his consistency.

That performance also puts him among the top free agents in Chicago sports history — if not into the No. 1 spot — as he became the last big acquisition before the Cubs launched one of the more stunning, competitive turnarounds in recent year.

They went from last place to 97 wins in his first year and won the World Series the next during a six-year run unlike any in franchise history — including five playoff seasons and three consecutive trips to the NLCS.

 

One of the best free agents in Chicago history?

“I can’t answer that part of the question,” Lester said. “But I know just as far as what Theo believe in me was the work, was the effort, that the effort day in and day out was going to be there and I was going to be prepared from the start.

“The fact of the matter is they understood that come Opening Day, whether I was pitching that day or not, they could pencil me in for 30 starts,” he added. “That’s something I really prided myself on and something Theo knew I would pride myself on. So it was something he could take a chance on the performance side of it, knowing that I would at least be there and would pitch.”

Lester, who made four Opening Day starts as a Cub, averaged 32 starts in his five full seasons in Chicago and a full-season equivalent of 12 during the 60-game pandemic season of 2020.

“I think that’s what I’m most proud of with the whole situation,” he said.

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