It's been nearly a decade since the Pittsburgh Pirates last handed out a multi-year contract to a free agent.
That player, pitcher Ivan Nova, actually had a decent run with the Pirates, pitching two seasons on his three-year, $26 million deal before getting traded to the Chicago White Sox in what amounted to a salary dump.
Like Nova, the team's largest free-agent expenditure, pitcher Francisco Liriano (three-year, $39 million deal), won't make an appearance on this list. Sure, their contracts stand as the largest out-of-house signings in team history — though, technically, both Nova and Liriano were re-signed after being allowed to test free agency — but they weren't total net-negatives for the team.