Left-handed starting pitcher Jordan Montgomery
There shouldn't be any argument that starting pitching needs to be at the very top of the Pirate shopping list heading into free agency, and the recently traded Jordan Montgomery is a proven lefty that would provide stability in any team's rotation.
He's having an extremely solid season this year, to the tune of a 3.38 ERA and 2.7 fWAR in 133 innings. His 7-10 record is misleading given the fact that he pitched over half of the season on the lowly Cardinals, and he'll undoubtedly be apart of the Texas Rangers playoff rotation when they make a push for a World Series this October.
He's currently signed to a 1-year, $10 million contract in his final year of arbitration. He's not quite in the Blake Snell or Eduardo Rodriguez tier of free-agent lefties, but he's a very solid mid-rotation option, and you could probably expect his new deal to be somewhere in the $15 million AAV range. He'd slot in perfectly behind Mitch Keller in the Pirate 2024 rotation.