Konnor Griffin extension chatter highlights how the Pirates mishandled Paul Skenes

What do you do when you have one of the best young players in baseball in your organization? The Pirates have had the luxury of considering this question twice in recent history, first with Paul Skenes and now with Konnor Griffin.

The boat has already sailed on a Skenes extension; he has already surpassed the value that Bob Nutting is willing to shell out. Griffin, on the other hand, provides the Pirates with an opportunity for a high risk, high reward extension.

The Pirates aren’t exactly strangers to handing out extensions. The team signed Mitch Keller, Bryan Reynolds, and Ke’Bryan Hayes to long-term deals early in their career. Keller and Reynolds signed after their first year of arbitration while Hayes signed a pre-arbitration extension.

Those, though, came during the heyday of the team-friendly contract (just look at the Braves). It’s harder to imagine Griffin getting locked up on a deal like that in today’s MLB.

Pirates could buck a trend by signing Konnor Griffin to a long-term extension

Even though the latest short-term megadeals make the prospect of Griffin sticking around with the Pirates seem unlikely, the Red Sox may provide a path forward for Pittsburgh.

Boston has built a solid core of young players on long-term deals. Cedanne Rafaela, for example, inked an eight-year, $50 million contract just 49 days into his big-league career. Rafaela isn’t as complete as Griffin is reported to be.

Dan Zangrilli of 93.7 The Fan suggests that a Griffin extension could have been in the works this winter as the Pirates negotiated with Kyle Schwarber’s representation. Griffin and Schwarber are represented by the same agency, which could have been a convenient path to a windfall in Pittsburgh.

Between Schwarber’s rumored nine-figure deal and a Griffin extension that could approach the same mark in total salary, the Pirates would have significantly increased their payroll if an agreement had come to fruition.

Signing Griffin now has its risks. Just look at the Red Sox, who wound up paying Kristian Campbell $2 million to play more than half the season at Triple-A last year. Had the Pirates not traded Hayes at the deadline, they’d be paying him $7 million to be one of the least valuable bats (and most valuable gloves) in the Majors.

But as the Pirates window of contention begins, now is the time to take some risks. And Konnor Griffin seems like a risk worth taking.