10 years after the Jon Lester signing, the Cubs need this trip down memory lane

Ten years ago today, the Chicago Cubs agreed to terms with free agent pitcher Jon Lester, the former All-Star and World Series champion with the Boston Red Sox and briefly Oakland A's. Cubs president Theo Epstein, who oversaw the first six years of Lester's career in Boston, brought Lester in to be an established centerpiece of the near-complete rebuild he was orchestrating on the North Side.

Safe to say that six-year, $155 million deal was worth every penny.

Lester's on-field statistics and accomplishments have been talked about numerously, and rightfully so, but looking back one can really appreciate what that deal meant to the franchise. The signing of Lester sent a strong message: they did not want to take another baby step or be just "good enough" - they wanted to be the BEST. The Cubs set the bar high. To be the best, they had to get the best, sparing no expense. No talk of "overperforming your numbers" or "good enough to get in like the ". It was "intelligent spending" by going out and getting a top target in his prime.

No doubt that deal would look particularly good for a pitcher of Lester's caliber if signed today, but the market has evolved a bit since then. Even if he was not as dominant of a pitcher as Max Scherzer, who signed the biggest deal that offseason, people knew the Cubs were getting something special with Lester. It was a sensical and reasonable deal even with the premium price and knowing the backend years had heftier financial commitments as he advanced in age. People weren't worried about the backend though, because it was going to make the Cubs notably better right then and there. Cubs fans were happy to deal with those last two "meh" seasons in 2019-2020 from an aging Lester in exchange for what he did from 2015 to 2018.

The Cubs need to find their 2024 version of the Jon Lester signing.

Lester was exactly what the Cubs needed, an experienced pitcher with a winning demeanor and one whose star shined brightest when the stakes were at the highest in October. His presence and leadership was notable for those young upcoming stars who, like Lester, were fearless in the big moment when they hit their primes. They do not win the 2016 World Series without him, he was one of the biggest factors in that run.

Cannot fail to mention the impression he made on the Cubs fans. Lester became the symbol of hope and later a symbol of triumph. He embraced the city as the fans embraced him. How many other players picked up the bar tab for fans on a given day? One day, he will likely have his likeness in the Cubs Hall of Fame at Wrigley Field underneath the bleachers. He will is a true "Cubs legend".

Fans who followed the team at the time will never forget where they were when the news dropped. Either up celebrating late at night when the news broke, or waking up to the great news the next morning. It was one of the biggest days in Cubs history and one of the best free agent signings in Chicago sports history along with the likes of Marian Hossa.