By Tim Kelly, Sports Talk Philly editor 
Jake Arrieta's free-agent contract with the Philadelphia Phillies was largely reported as a three-year/$75 million contract, because that's what it's most likely to end up being.
However, after one of the more frustrating free-agent stints in recent memory, Arrieta's agent, Scott Boras, negotiated a fairly complicated deal for one of his highest profile clients.
After year two of the contract, when Spotrac notes that Arrieta will have already collected $55 million from the Phillies, the former Cy Young Award winner can opt-out of his contract and test the free-agent market again. The Phillies could prevent Arrieta's ability to test free-agency by exercising $20 million options for 2021 and 2022.
Jon Heyman of FanRag Sports, in a piece discussing the Chicago Cubs attempt to retain Arrieta, says that Arrieta thinks there is a distinct possibility that the Phillies are ultimately faced with the decision to exercise the two options:
Ultimately, Arrieta got a $75 million, three-year deal with the Phillies that includes an opt-out after two years, by which time he will be paid $55 million (or a rather $27.5 million a year) and an extension option for the Phillies at $40 million over two years. Arrieta is said to feel good about the AAV he got, the chances he could turn it into something even better and also the chances that the Phillies “opt in” for him for the final two years.
