During the totality of the Ben Cherington regime in Pittsburgh, the Pirates still haven't signed a free agent to a multi-year deal. It's not entirely fair to blame that on him either, has he has reportedly offered players those contracts, with Shota Imanaga being the most notable potential recipient. Of course, the budget's always capped, and the team has to be appealing enough for a veteran to want to slgn on long-term before it can happen. Notably, Chris Rose of Jomboy Media just predicting that this year's Pirates will snap that dry spell in a unique way, by signing a veteran catcher across the state.
MLB personality has wild idea for Pirates to break multi-year deal dry spell this winter
