Chicago Cubs: Jon Lester reaches an incredible milestone

Jon Lester is one of the most important players in the history of the Chicago Cubs. He is one of the first people to realize that they were building something special so he signed with them when he became a free agent. He then was one of two aces on a staff that led them to a World Series championship in 2016. There was a lot of success during his time with the Cubs.

Unfortunately, things didn’t end the way you’d like to see them end between an organization and a superstar like Lester. He wanted to take a discount to come back to the Cubs but they didn’t want him. The Cubs believed they were a winning team going into 2021 but they didn’t think Lester could help with that. They were wrong.

Lester signed a deal with the Washington Nationals. Things didn’t go well there in terms of wins and losses so they flipped him to the St. Louis Cardinals at the trade deadline. The Cubs deciding they didn’t want to be loyal to their guy led to him pitching for their most bitter rival.

Lester, on Monday, recorded his 200th career win in St. Louis’s ninth straight game. It is a milestone that not many reach anymore because of starter/bullpen management but Lester has stood the test of time. He isn’t s superstar anymore in terms of his production but he is a quality arm and a quality dude. 77 of Lester’s wins came with the Cubs over six years.

Jon Lester is one of the greatest players in the history of the Chicago Cubs.

It was a curious move when St. Louis made it because it didn’t look like they were going to compete for a playoff spot. Now, after nine straight wins, it looks like they have a real chance of being a Wild Card team in the National League. Lester has been a big part of that (4-1 with St. Louis) as he found something while pitching there that he didn’t have in Washington.

If St. Louis does in fact make it, they will likely play either the San Francisco Giants or Los Angeles Dodgers in the one-game Wild Card. They would be underdogs in that game but you just never know. The fact that Lester could be participating in the playoffs once again speaks volumes.

St. Louis turning it around right when he got there makes perfect sense. The Cubs absolutely should have kept him because he just changes the way things are done when he is on a semi-talented roster. Despite Chicago’s hatred of the Cardinals, it is cool to see Lester having this success because of what he meant to the Cubs and the city.