In 2014, the Houston Astros made history by signing Jonathan Singleton to a contract extension: he was the first player with no Big League service time to sign such an agreement. The deal was a five year contract worth $10 million that included three option years that could net Singleton up to $20 million dollars on top of his guaranteed money.
The deal garnered its share of criticism. Pitcher Bud Norris called the deal "terrible", noting he wished Singleton "listened to the (Players') union and not his agent". Norris isn't exactly known for his economic prowess or for having good opinions, but he's not completely wrong.