Perrotto: Pirates Should Already Be Thinking How to Keep Paul Skenes

Bob Nutting has shown over the past two years that he is occasionally willing to take a leap of financial faith.

The Pittsburgh Pirates owner has signed off on two long-term deals to keep players under contract through the decade’s end. Third baseman Ke’Bryan Hayes received an eight-year $70-million contract in 2022 and left fielder Bryan Reynolds signed for eight years and $106.75 million last year.

Nutting was convinced by general manager Ben Cherington and the baseball operations department that Hayes and Reynolds were sound investments. If nothing else, it at least helped Nutting improve a bit on his image of being cheap and not caring about winning.

However, now is the time for the Pirates to make an even bolder move. They need to sign pitching prospect Paul Skenes to a long-term contract. Now.

I understand the arguments against such an idea.

Skenes has yet to pitch in the major leagues and has logged just 6.2 minor-league innings in his budding professional career. There is also the fact that pitchers carry inherent health risks with tendons and ligaments that get stressed to the point that they can tear at any time.

All are valid points. However, I also think the Pirates must leave their comfort zone and enter a long-term relationship.

Skenes had one of the greatest seasons of any pitcher in college baseball history last year. He helped lead LSU to the College World Series championship a year after transferring from the Air Force Academy and was named College Player of the Year by Baseball America.

Skenes wasn’t putting up overpowering statistics against inferior competition, either. He was playing in the Southeastern Conference, which is as good as it gets at the college level.

Those are all reasons the Pirates chose Skenes first overall in last year’s amateur draft and signed him for $9.2 million during cordial negotiations.

While there is never such a thing as a can’t-miss prospect, I have yet to talk to one executive or scout throughout baseball who has anything negative to say about Skenes. Everyone loves his size, pitch arsenal, competitiveness, intelligence and maturity.

The feeling is unanimous that Skenes will blossom into a No. 1 starter and perennial Cy Young Award candidate.

Those are the type of pitchers who break the bank. Think about another first overall draft pick by the Pirates, Gerrit Cole, who signed a nine-year, $324-million contract with the New York Yankees when he reached free agency in 2019.

The Pirates almost certainly wouldn’t be able to keep Skenes in Pittsburgh throughout his entire career. But they could offer him something like an eight-year contract that would cover all his arbitration-eligible seasons and the first two years after he would become eligible for free agency.

By then, Skenes would be 29 years old and could still enter the open market in the prime of his career to chase a big contract.

The Pirates would be taking on some risk if Skenes were to be injured or not live up to the high expectations.

Skenes, too, would be gambling by passing up the chance to make more money by going through the arbitration process every year. However, he would also have financial security should his career get derailed.

The concept of signing players without major-league experience is beginning to become at least somewhat common. The Milwaukee Brewers and outfielder Jackson Chourio agreed to an eight-year, $82-million deal at the Winter Meetings in December and the Detroit Tigers signed infielder Colt Keith to a six-year, $28.6-million contract last month.

Keith summed up the situation well during the press conference following his signing.

“There are positives and negatives and risks on both sides,” Keith said. “Worst case for both of us — the organization and myself — is that I don’t pan out and I end up with security financially for me and my family for the rest of our lives. The best case for both of us is that all of the option years are exercised, we win a couple of World Series and bring them back to Detroit and I make myself a boatload of money.”

It really could be a win-win situation in Skenes’ case, too, and something the Pirates need to explore.