Mark Madden's Hot Take: Pirates must trade prospects to bolster MLB roster, maximize Paul Skenes' window

The Pittsburgh Pirates’ window to contend extends as long as they have pitcher Paul Skenes. That’s through somewhere around 2028 or so, whenever owner Bob Nutting mandates trading Skenes to avoid paying him $25 million or whatever via arbitration.

There’s no point fantasizing that the Pirates can keep Skenes into his free-agent years and for the long term. There’s zero chance.

Yeah, they kept Ke’Bryan Hayes, Mitch Keller and Bryan Reynolds. Those three are ham-and-eggers who declined the risk of free agency. There’s no comparison to Skenes. He’s a unicorn.

This space recently pushed the need to trade for bats. To get Skenes more support. Now, let’s get more specific.

The Pirates must trade their very best prospects to maximize the Skenes window. Nobody should be exempt, not even top talents like infielder Termarr Johnson or pitcher Bubba Chandler.

Not that I have much faith in GM Ben Cherington to make the right deals.

But by the time Johnson, Chandler and their ilk fulfill their presumed timetables and can contribute on the big-league level, Skenes will either be gone or have one foot out the door. Plus, there’s no guarantee with most prospects. (See Davis, Henry.)

More sports

• 'We feel urgency': Pirates GM Ben Cherington expects improvement but isn't ready to panic
• Bailey Falter sharp, Pirates put up 11 in win over Braves
• Mark Madden: Giving Cam Heyward a contract extension not worth the risk for Steelers

If you keep your prospects, the cycle repeats itself: Develop prospects, then trade them for more prospects. Kick the can down the road. Hope you can keep fooling the marks, and why wouldn’t Nutting think that?

But this is different. Skenes gives the Pirates the best chance they may ever have. Even the densest of you must be able to see that.

It means adding payroll. So, it probably won’t happen. Nutting won’t augment salaries very much, as witnessed in 2015 when he immolated a 99-win team because it was getting expensive. (Not even crazy expensive.)

But this team can’t improve enough from within. That was evident Wednesday and Thursday when Jared Jones and Skenes both made good starts vs. San Francisco, then exited and watched the Pirates blow big leads in both games.

Jones and Skenes are brilliant. But they’re not near enough.

In 2014 and 2015, the Pirates got their bats shoved up an uncomfortable place when they faced lights-out pitchers in a single-game wild-card situation: San Francisco’s Madison Bumgarner in ‘14, the Chicago Cubs’ Jake Arrieta in ‘15. Neither dropped the ball.

The Pirates now have that pitcher in Skenes. But if they sneak into a wild card, that round of the playoffs is now best-of-three. That’s ironic, but it figures. Now that the Pirates have the unhittable guy.