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Could (and should) the Phillies make a play for Clayton Kershaw this winter?

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On Episode 187 of “Hittin’ Season,” host John Stolnis takes a look at the chances of the Phillies adding the best pitcher in baseball this off-season.

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MLB: Arizona Diamondbacks at Los Angeles Dodgers Jayne Kamin-Oncea-USA TODAY Sports

He’s the best pitcher of this generation and he might become available to the highest bidder in a matter of months.

Let the wild speculation begin.

Jon Heyman’s latest piece runs down the potential free agent market for Dodgers’ ace Clayton Kershaw, who can opt out of the final two years of his contract with Los Angeles that is due to pay him $32 million in 2019 and $33 million in 2020. He will be just 31 and 32 years old in those two seasons, and Heyman says the “scuttlbutt — to no one’s surprise — is that he will use the opt-out at season’s end to better his financial standing, either with a higher AAV or longer term.”

Of course, even if he does opt out, the Dodgers would still be the overwhelming favorites to retain his services (Heyman’s cloudy odds-scoring system puts it at 3:5 he stays, whatever that means). He is the face of the franchise, one of the five or 10 best pitchers of all time and a sure-fire future Hall of Famer. He’s a Dodger icon. Letting him go is almost unthinkable.

That being said, if it happens, could the Phillies pounce? Should they?

Heyman gave the Phils the 5th-best odds to land the left-handed hurler, putting the number at 25-1.

Imagine a starting rotation of Kershaw/Aaron Nola/Jake Arrieta, with an improved Nick Pivetta and/or Vince Velasquez at the end of it.

The Phils, of course, are expected to be major players in this off-seasons free agency bonanza, with Manny Machado and/or Bryce Harper presumably their top targets. As Heyman noted, the push for Machado appears to be real, with the Phils’ Baltimore connections in the front office well documented by this point. And with just $68.9 million committed to the 2019 payroll as of now, the Phillies could add a premier position player and still have room for Kershaw, should he become available.

Also, not for nothin’, but Heyman’s last line “They also are very rich, a lot richer than you think,” (emphasis added by me) is certainly interesting and cryptic. What does he mean by, “a lot richer than you think?” Could that mean Middleton doesn’t give a hoot about the luxury tax and would be willing to fly right on past it to sign all the players he wants? Hmmmmm.

While the Phillies certainly could make a run at Kershaw in the unlikely event he becomes available, should they?

When Kershaw is healthy, he’s a monster. He’s 145-66 with a career ERA of 2.35. He has averaged 9.87 strikeouts per nine innings, and has a career WHIP of 1.00. Opponents have hit .203 against him for the entire time he’s been a big league pitcher.

However, there are some injury concerns. For the last two seasons, Kershaw has missed chunks of time with back injuries. He made just 21 starts in 2016 because of a herniated disk in his lower back, and last year missed five or six starts because of a lower back strain.

Now in his early 30s, will his back hold up as he ages? If not, how much will it hinder him? And if Kershaw is looking to opt-out of $33 million and $34 million seasons each of the next two years, how much of a raise is he going to want? How long of a contract will he demand? Would the Phillies give a 31-year-old pitcher with a history of back problems a five or six-year deal worth $30-35 million a season, even if it is Clayton Kershaw?

Signing Kershaw would be a high-risk, high-reward maneuver, one I’m not sure this front office is anxious to make. And hey, it’s highly unlikely he’s going to leave Los Angeles anyway, so this is probably a moot discussion. But it’s also a fascinating possibility.

On Episode 187 of Hittin’ Season, host John Stolnis explores the possibility of Kershaw to the Phils, talks to ESPN’s Jerry Crasnick about Gabe Kapler and the NL East, and Phils beat writer Meghan Montemurro of The Athletic Philadelphia talks about the Phillies recently-completed road trip and the team’s burgeoning mental skills department.