Chicago Cubs have come full circle letting Jon Lester walk to Washington

The Chicago Cubs decide to let Jon Lester sign with the Washington Nationals on a team-friendly one-year deal.

Dec. 10, 2014. It was a Wednesday, not that the day of the week matters. More importantly, it turned out to be the day new Chicago Cubs manager Joe Maddon proclaimed, “The Cubs won the baseball lottery.”

Jon Lester said yes to his friend, Cubs president Theo Epstein by choosing the still-rebuilding Cubs and Wrigley Field over his familiarity with Fenway Park and the Boston Red Sox. Less than two years later, Maddon’s pronouncement proved correct. No one player was more instrumental in the Cubs winning a World Series and ending a 108-year drought than October-November-clutch Lester.

By signing a contract with the Cubs, albeit a pact that was well over a total of $150 million, Lester sensed the Cubs were headed in the right direction when there was still some skepticism. Others, like World Series MVP-to-be Ben Zobrist, soon followed. The foundation set in place by Epstein was first validated from a two-time World Series champion. It mattered.

Lester saw a farm system rich in high-end talent, a manager he was comfortable with in Maddon and believed there were additional dollars to spend. In addition, he trusted Epstein to make the right decisions to put the final pieces in place.

While Lester had confidence in what the Cubs were doing, he did his part by rising to the proverbial occasion when it mattered most.

In Game 1 of the 2016 NLDS, Lester beat the San Francisco Giants 1-0. Then in the NLCS, he was the co-MVP as the Cubs beat the Dodgers in six games, reaching their first World Series since 1945.

Then on Oct. 30, 2016, the Cubs trailed Cleveland 3-1 in the World Series with a do-or-die Game 5 at Wrigley. Lester pushed through six intense innings of one-run ball before handing it over to Carl Edwards and Aroldis Chapman to keep the Cubs alive as they beat the Indians 3-2.

Historically, the Cubs lose that Game 5 every time. They had lost two in a row at home. Losing streaks in the playoffs never were turned around as the pressure built. The weight of 1908 seemed to suffocate team after team.

Incredibly, the Cubs had lost three in a row to the underdog Padres in 1984, followed by three to the Giants in 1989, the Braves in 1998, the underdog Marlins in 2003, and then swept by Arizona in 2007 and the Dodgers in 2008. Then there was a four-game sweep by the Mets in 2015. Cubs history indicated that once the tide turned negative, there was no getting it back.

Lester changed that in that Game 5 and then was back at it in the late innings of Game 7 on only two days rest as Maddon had a bad night. Kyle Hendricks was cruising, having allowed only one run on four hits with two outs in the 5th inning. Hendricks had retired seven batters in a row when Maddon inexplicably called for Lester after a two-out walk to Carlos Santana.

The Cubs defense then immediately let Lester down. David Ross threw Jason Kipnis’ swinging bunt into right field, setting up runners at second and third, then couldn’t block a wild pitch in the dirt, allowing two runs to score. 5-3. Cleveland had the momentum.

Lester steadied when most would have wobbled. He shut Cleveland down, retiring nine of the next 11 batters into the 8th inning, easing the pressure. Then Maddon popped out of the dugout on a two-out Jose Ramirez infield single. Lester looked like he could have secured the final four outs. Even so, three innings of crucial Game 7 work plus Game 5 is remarkable. Ben Zobrist won the MVP of the series, but it could have easily been Lester.

Now the painful part: 2021. The Cubs are closer to rebuilding than contending. Epstein has left, along with Kyle Schwarber. More seem to be on their way out. Lester just turned 37 years old. The finish line is in sight for his Hall-of-Fame career, as is 200 career wins. Lester is seven shy of the milestone and wanted to reach it as a Cub. He wanted to return despite their current transitional state. The Cubs said no.

If the Cubs were actually trying to be anything other than mildly competitive in the weak National League Central, it would make baseball sense to move on from an aging pitcher. This feels more like the Cubs are choosing the bottom line over a player who earned so much more.

Lester gave thanks to Cubs fans on Halloween weekend, buying beers, while the Cubs are saying thanks but no thanks.

Lester leaves Chicago as the greatest free-agent signing in Cubs history. His resume is impeccable — playoffs in five of six years, three trips to the NLCS and a World Series championship. His choice to come to Chicago will forever be appreciated.

His exit reminds fans of the Cubs they used to know. That the glory years of Theo, KB, Javy, Riz, Schwarbs, Maddon, #NVRQT are over.

“It’s gonna happen” miraculously happened with Lester leading the way.

Nothing lasts forever. Change is inevitable and money matters, as is the case here with Lester being pushed out the door.