Pirates reach five-year extension with All-Star RHP

Keller had already agreed to a one-year, $5.4425M deal for the upcoming season, avoiding an arbitration hearing in the process. Assuming this new contract now overwrites that deal, he’ll be guaranteed four years and $71.5575M in new money. That aligns closely with the four-year, $73.5M extension between the Twins and Pablo Lopez a year ago. Lopez, like Keller now, had between four and five years of big-league service at the time of the agreement.

A 2014 second-round pick and longtime top prospect, Keller has taken major steps forward over the past two seasons, pitching to a combined 4.08 ERA in 353 1/3 innings. That solid but unspectacular ERA masks some more promising underlying trends. Keller’s 2022 season took off when he added a sinker to his arsenal in mid-May, helping to take some pressure off what had been a rather hittable four-seam fastball. He was dominant for the first two-thirds of the 2023 season before stumbling with a handful of meltdown starts over the final couple of months as he pitched to a new career-high workload (194 1/3 frames).

That ugly start in 2022 and similarly rocky finish in 2023 bookend a stretch of 41 starts that underscore the upside the Pirates are chasing with this signing. At his best from 2022-23, Keller rattled off a stretch of 240 1/3 innings of 3.25 ERA ball, fanning 23.5 percent of his opponents against a sharp 7.9 percent walk rate and strong 48.4 percent ground-ball rate. And even with the tough finish to his 2023 campaign, Keller ended the year with career-best marks in strikeout rate (25.5 percent), walk rate (6.7 percent), average exit velocity (87.7 mph) and hard-hit rate (35.6 percent). There are plenty of arrows pointing up with regard to the 6-foot-2, 220-pound righty, and the Bucs surely view him as someone capable of that low-3.00s ERA who can team with 2023 No. 1 overall pick Paul Skenes to anchor the rotation moving forward.

Skenes figures to debut this summer, and the Keller extension gives the organization a chance at a dynamic one-two punch atop the staff for the foreseeable future. For the 2024 season, the Bucs’ rotation will also include veterans Martin Perez and Marco Gonzales, though neither lefty is guaranteed anything beyond the current campaign. (Gonzales has a $15M club option with no buyout.)

The Pirates’ ability to either develop or acquire sufficient rotation help beyond the 2024 season will be critical to their chances of reversing a nearly decade-long run of losing baseball at PNC Park. Prospects like Quinn Priester, Kyle Nicolas, Jackson Wolf, Jared Jones, Anthony Solometo and Bubba Chandler give the Pirates a solid stock of promising young arms alongside Skenes. Each of Skenes, Jones and Chandler has garnered some top-100 fanfare this season (as Priester has in the past).

Of course, the Pirates’ history of developing starting pitching has been suspect, at best. Much of the struggles came under the now-former front office regime, but we’ve seen touted talents like Gerrit Cole, Tyler Glasnow, Jameson Taillon and Joe Musgrove all struggle to reach their ceilings with the Bucs before being traded. Cole, Glasnow and Musgrove, in particular, broke out with their new clubs. Even Keller took a long road to reach the form that led to today’s five-year agreement. It’ll be imperative for the Pirates that they improve their development of young pitchers and/or find help outside the organization. Notably, they’ve been in constant contact with the Marlins about Miami’s bevy of young pitchers and have explored other trade possibilities as well.

Keller joins outfielder Bryan Reynolds and third baseman Ke’Bryan Hayes as core pieces the Pirates have signed to long-term deals over the past few years. It’s a breath of fresh air for Bucs fans who’d grown accustomed to seeing their best players traded as their arbitration prices escalated. The long-term deals signed by each player don’t necessarily preclude eventual trades — as evidenced by Andrew McCutchen — but it’s nevertheless an encouraging trend for Pittsburgh fans to see a trio of extensions that each top $70M in guaranteed money, considering their $60M extension with Jason Kendall back in 2000 stood as the richest in franchise history for upwards of two decades.

Each of Keller, Reynolds and Hayes are now signed through at least the 2028 season — the same year that the team’s control windows over shortstop Oneil Cruz and outfielder Jack Suwinski extend. That quintet, paired with Skenes and catchers Henry Davis and Endy Rodriguez, could form the nucleus of the Pirates’ next contending club. Reynolds’ seven-year, $100M extension and Hayes’ eight-year, $70M pact are both generally affordable, even by the Pirates’ modest standards, which should give the Bucs flexibility to supplement that core in other ways.

It’s unlikely the Pirates ever dive into the deep end of the free-agent market. But if owner Bob Nutting ever decides he’s finally comfortable spending in even the second tiers of the open market — Francisco Liriano’s three-year, $39M contract is the largest free agent signing in Pirates history — the Pirates would have the chance to complement their growing foundation with some meaningful talent and break away from their lengthy run in the NL Central cellar.