Atlanta Braves president of baseball operations Alex Anthopoulos, who just signed a much-deserved contract extension, has hit on a lot more of his gambles than he’s missed.

On November 4th, 2020, Anthopoulos took a chance on a pitcher who would be entering his age-37 season after he suffered a shoulder injury the year before, signing Charlie Morton to a one year, $15M contract.

Morton had appeared in two straight All-Star games and finished in third place in the AL Cy Young voting for 2019, but struggled in 2020 and subsequently became a free agent.

Safe to say that gamble paid off – Morton’s returned 8.5 WAR over the last three seasons and is back for the 2024 campaign.

Former Los Angeles Dodgers starter and future Hall-of-Famer Clayton Kershaw’s situation is not a one-to-one comparison to Charlie Morton, but it is similar. Kershaw has been named an All-Star for the past two seasons and he is coming off of a year where he finished with a 13-5 record and a 2.46 ERA. His season did not end on a high note, though, as he started for LA against the Diamondbacks in the NLDS and allowed six runs on six hits as he only recorded one out before being pulled from the game.

After the season ended, Kershaw announced that he would be having surgery to repair the glenohumeral ligaments and capsule of his left shoulder. He plans on being back by the summer of 2024, but the timeline is not set in stone. It all depends on how he progresses during rehab.

In the end, Kershaw agreed to a $20 million, one-year contract with the Dodgers for 2023. Following his great 2021 season, Charlie Morton re-upped for that exact deal with the Braves in 2022. AA appears to be the leader in giving veterans, primarily pitchers, contracts worth $20 million for a year.

Do you recall the Cole Hamels deal? In 2020, AA signed Cole Hamels and Ozuna to one-year, $18 million contracts. Although Ozuna is hardly an older pitcher, you get the idea. For athletes who are uncertain about their season, AA loves to provide contracts like this one. Call it a “prove-it” season. Kenley Jansen and Drew Smyly are other welcome additions to that roster. Josh Donaldson’s contract was a touch higher, coming in at $23M, but provided further evidence of that.

Signing Clayton Kershaw is an idea that a lot of people have not pondered yet but it is a possibility. With LA spending $1.1 billion with a “B” this offseason, I don’t think he will be heading back to the Dodgers.