MLB Milestone Tracker: Five things to watch for in 2020

ANAHEIM, CA - JULY 28: Los Angeles Angels First base Albert Pujols (5) is all smiles after his team beat the Baltimore Orioles on July 28, 2019, at Angel Stadium of Anaheim in Anaheim, CA. (Photo by Carrie Giordano (Jesenovec)/Icon Sportswire via Getty Images)
ANAHEIM, CA - JULY 28: Los Angeles Angels First base Albert Pujols (5) is all smiles after his team beat the Baltimore Orioles on July 28, 2019, at Angel Stadium of Anaheim in Anaheim, CA. (Photo by Carrie Giordano (Jesenovec)/Icon Sportswire via Getty Images) /
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(Photo by Dylan Buell/Getty Images)
(Photo by Dylan Buell/Getty Images) /

Five MLB Milestones to watch for in 2020

Jon Lester- 200 Wins

This is an interesting milestone to keep an eye on. Zack Greinke surpassed the 200-win threshold this season and Jon Lester is going to be the next pitcher to do so.

Lester went 13-10 for the Chicago Cubs this season, making his all-time win total 190. Lester should definitely surpass that mark in 2020 since he has won at least 10 games every season since 2013.

Now that CC Sabathia has retired, Lester has the third most wins amongst active pitchers, only Greinke and Verlander have more.

As he heads into his 15th season, Lester’s Hall of Fame chances are a bit slimmer than other active pitchers ahead of him on the wins list. His career ERA is 3.56, which is a little high for Cooperstown. He has finished top five on three Cy Young ballots but has never won the award.

However, the lefty has won three World Series, has been an above-average starter for a long time, and will certainly have a better case with 200 wins.

The five-time All-Star is going to be 36 at the beginning of next season. He is coming off a poor season but is looking to rebound in 2020. If he wins at least 10 games, he will climb up to 116th on the all-time wins list.