Pirates showing interest in intriguing starting pitcher

The Pirates are among the teams with some interest in free agent Jack Flaherty, reports Jeff Jones of the Belleville News-Democrat. The Bucs are interested in a short-term pact with their former division-rival, per Jones.

Interest on a short-term deal, of course, is contingent on how the remainder of the market views Flaherty. At 28 years of age, he’s the youngest starting pitcher with ample big league experience available this winter. However, Flaherty is also coming off a down season that saw him pitch to a 4.99 ERA in 144 1/3 innings between the Cardinals and the Orioles, who acquired him prior to the trade deadline.

Not long ago, Flaherty looked like a burgeoning ace. The former first-round pick and top prospect turned in a 3.34 ERA over 151 innings back in 2018, his first full big league season, and followed it up with even better numbers in 2019. At a time when most pitchers in the league were falling victim to what we now know was a juiced ball in 2019, Flaherty was delivering the best season of his still-young career: 196 1/3 innings, 2.75 ERA, 29.9% strikeout rate, 7.1% walk rate. Unfortunately for both him and the Cardinals, injuries (primarily shoulder troubles) limited him to 154 1/3 innings from 2020-22 combined. Last year marked a return to better health but also lesser results.

Flaherty figures to have multiple scenarios he could pursue. A straight one-year deal or perhaps a two- or three-year pact with an opt-out would allow him the opportunity to reenter free agency not far down the road — ideally on the heels of a better platform season. In the past, a straight one-year deal was often the norm for a player in this situation. Increasingly, however, we’ve seen free agents coax two-year deals out of teams, with the second season being a player option.

There’s also the possibility of pursuing a longer-term deal that would still allow Flaherty to return to market at a reasonably young age. In the past, we’ve seen some free agents around the same age (e.g. Phil Hughes, Tyler Chatwood) take three-year deals that provided some financial security while also affording an opportunity to get back to the market in time for another chance at a contract of note. A three-year deal for Flaherty would cover his age-28, age-29 and age-30 seasons. If the market bears it, that arrangement could effectively set Flaherty for life financially and still create the chance to hit the market in search of a more elusive five- or six-year commitment.

As for the specific fit with the Pirates, it’s a strong one regardless of which type of contractual structure Flaherty prefers. While Pirates ownership might balk at a multi-year commitment of note, Pittsburgh is in dire need of rotation help. Mitch Keller is the only established starter on the roster now that righty Johan Oviedo will miss the 2024 season due to Tommy John surgery. Flaherty would slot comfortably into the starting staff and do so knowing that he’d have a long leash regardless of how he starts the season. Other options on the Pittsburgh staff currently include Bailey Falter, Roansy Contreras, Quinn Priester and Luis Ortiz. This past season’s No. 1 overall pick, right-hander Paul Skenes, will likely debut at some point in 2024 as well.

With regard to the team’s payroll, the Pirates only have three players under contract for the 2024 season (Ke’Bryan Hayes, Bryan Reynolds, Ryan Borucki) and another four arbitration-eligible players (Keller, David Bednar, Connor Joe, JT Brubaker). Roster Resource projects just a $53M payroll for the upcoming season. Even by the Buccos’ standards, that’s at the bottom of the scale. Pittsburgh opened the 2023 season at $73M and operated under a franchise-record $100M back in 2016. There ought to be plenty of room to add multiple starters — even if some money is perhaps earmarked for another reunion with Pirates icon Andrew McCutchen.

Whether Flaherty is a part of the solution or not, the Pirates simply need to bring in multiple arms this winter. Flaherty’s youth and track record (particularly that 2018-19 run) give him more upside than most free agents in the second and third tiers of free agency, but that might also make him a popular target and push the bidding beyond the comfort zone of the perennially low-spending Pirates.