The off-season of self-examination looms over the Yankees organization. Who will fill in for the Yankees’ porous starting pitcher rotation? The issue is only getting worse following the retirement of long time Yankee starter, C.C. Sabathia. Can the Yankees somehow lure pending free agent Gerrit Cole (of the Astros) into joining the Dark Empire of New York? Does Aroldis Chapman use his opt-out clause with about $34 million and two years left on the contract?

Confronting these questions is more uncomfortable for Yankees fans and the organization itself, considering New York had a true chance to produce a different ending to their season. Let’s start by reviewing Game 7 of this year’s World Series. The Astros refused to pitch Cole, who was prepared to participate in Game 7 (if needed). Both the Nationals and Astros used every pitcher in their bullpen for all games up to Game 6.

If you’re unable to take advantage of the luxury of bringing Gerrit Cole to your rotation, one decent backup plan could be another former number one draft pick, who dominated the Postseason leading to a World Series MVP. Stephen Strasburg opted out of his four year, $100 million contract with Washington. Strasburg will certainly move past this in this year’s free agency. The former Cy Young finalist is 31 years old, so he likely won’t ask for as long of a contract as Gerrit Cole, but pitching aces are rare to come across.

Strasburg had a killer season, leading in numerous statistical categories, including leading the National League in innings pitched (IP), setting a career record in strikeouts with 251 strikeouts (K), and he went undefeated in the 2019 Postseason while leading playoff pitchers in earned run average (ERA) with a 1.98. Another small feat: oh, um, World Series MVP! Stephen Strasburg picked the perfect time to understand his MLB value, and now it’s his turn for a payday!

With Cole and Strasburg about to get paid after their postseason brilliance, this year is the year for Madison Bumgarner (also formally known as MadBum) to cash in on his October success,… just five years later. 2019’s playoff superstars helped us comprehend how crazy Bumgarner’s 1.03 ERA in an MLB postseason-record 52 and two-thirds innings in 2014 was. Bumgarner’s greatness lead the San Francisco Giants to their third title in five seasons.

It’s difficult to comprehend that Bumgarner is just 30 years old. With all these workhorse innings in San Francisco, and all those additional frames he stacked up in not one, but two intense October runs, this weapon is possibly the perceived age rather than the actual one as Bumgarner is now a great starter, but no longer the lights-out ace he once was. However, Bumgarner can perhaps be the top-tier MORP (marginal value above replacement player) choice to match up with Mike Minor and Lance Lynn in Texas.

So when somebody asks me, should these three pitchers get paid, I evaluate every factor in the situation. Yes, they’re all either a year over 30 or closing in on 30. Yes, most pitchers abilities to produce outs and wins decline after they turn 30 years old. Nonetheless, this trio of free agents still has more than enough juice in the tank to make several more playoff pushes. I’m going to be honest with you, I don’t see the Giants making the playoffs anytime soon. So for Bumgarner to make it to the Postseason again before the end of his career, a change of scenery wouldn’t hurt.

Strasburg has the option to sign with the Nationals again, but I don’t see that happening because his contract will be much smaller, considering Juan Soto and Victor Robles are in the Majors to stay, Patrick Corbin just received a $140 million contract for six years and Trea Turner has been guaranteed $7.5 million (entering arbitration in a couple years).

I think the big winner of the 2020 MLB free agency will be Gerrit Cole. He performed at peak performance all year and the Yankees have a little money saved up. Will Cole settle for a low salary contract, so the Yankees can build more around him or will he cash in big? My prediction: Gerrit Cole will look out for Gerrit Cole, meaning he will go for the big contract.

This won’t necessarily be a problem for the Yankees. If Didi Gregorius doesn’t sign back with them, Gleyber Torres will become the everyday shortstop, D.J. LeMahieu will become the second basemen, Gio Urshela will become the everyday third basemen based on the fact that Miguel Andujar is on the trading block and let’s not forget about Luke Voit. Even though he had a mediocre sophomore season, Voit will be looking to bounce back from his sophomore slump and get the Yankees back to the Promised Land.