Starting pitcher Rich Hill
If Santana isn't the most likely Pirate to be traded then Rich Hill is. The veteran lefty could be one of the few starting pitchers available, which will help drive up his trade value. Combine this with Hill being a pending free agent, and he is likely to be traded.
Hill made his 21st start of the season on Tuesday night. In 4.1 innings pitched Hill allowed 2 runs on seven hits, two walks, three strikeouts, and a home run allowed. On the season, Hill now owns a 4.82 ERA and a 4.42 FIP in 114 innings pitched.
Much like Santana, Hill brings a veteran presence and leadership aspect to a clubhouse that teams will value. Hill is also a workhorse who will take the ball every five days, and more often than not give a team 5 or 6 innings.
Hill also has postseason experience. The 43 year old has pitched in 13 postseason games with 12 being starts. He has pitched 53 innings in these 13 outings, posting a 3.06 ERA, 3.97 FIP, and 28% strikeout rate. So not only does Hill have postseason experience, he has pitched well in the postseason.