Now, this may be the most likely signing of the ones I have suggested. Drew Pomeranz would be by far the cheapest of the bunch. Ever since his All-Star season in 2016, he has struggled to say the least. A 6.08 ERA in 2018 with the Red Sox, a 5.68 ERA with the Giants earlier this season, and now a 5.14 ERA in the short time he has been with the Brewers after a deadline deal sent him their.
Neal Huntington is on record saying that they will be looking at all options in free agency following the 2019 season, but will focus more on bringing in an Edinson Volquez and J.A. Happ type of pitcher. Pomeranz fits that description for me. A starter that has had success in the past, but has struggled recently. That seems to be the type of starters Huntington goes after. Not to mention that Pomeranz would likely only command a couple million dollars this winter.
The tough reality of being a Pirates fan is that big money free agents simply will never sign here. They constantly have to shop in the bargain bin and hope that the stars align in the coming season. Guys like Cole or Strasburg will never even be entertained in the front office, so it will more than likely be guys like Pomeranz, Roark, Pineda, etc.