Dickey is due to make $5 M next season at age 38. My proposal would be to trade Gregory Polanco OR Alen Hanson AND lesser prospects (like a Jeff Locke) for Dickey, and instantly offer him the 2 year, $26 million extension that he sought in New York. Alternatively, we could trade Jameson Taillon, which would be an overpay, and get Dickey and another MLB ready piece in return. I won't speculate as to who that extra player or players would be, but imagine getting back someone who would make the deal approximately "fair".
I think Dickey is the ideal candidate for the Pirates to gamble on. Due to Dickey being lowballed by New York, it is clear that the Mets are counting on him to severely regress. He is getting old, but as a knuckleballer, I think Dickey is a unique case, and he could be a valuable asset for the Pirates. In addition to helping the Pirates win more games, Dickey would be a great attendance draw at PNC Park. And if he helps the Pirates get over the hump, it would be well worth it.
I wouldn't want to trade any of our top prospects for one year of Dickey, so we would need assurances before-hand that Dickey was willing to sign an extension here in Pittsburgh. I do believe that the Pirates (barely) have the resources to make such an extension. The Pirates won't be able to sign any aces in free agency. This might be the best chance they have at acquiring an established ace to really put the Pirates into serious playoff contention.