Jason (Steven Pasquale), furious over Ian's (also Steven Pasquale) out of control spending, cuts off his cash flow... only to wake up at the wheel of a "borrowed" sports car with a trunk full of money and an angry drug dealer in his rearview mirror.
Ian (Steven Pasquale) falls for a woman in D.I.D. therapy, but when Jason (also Steven Pasquale) suspects she has a life-threatening condition, he races to cure her - a cure that may mean she no longer loves Ian.
Ruben (Lin-Manuel Miranda) arranges for a gang to "mug" Ian (Steven Pasquale) so that he can get a sample of his spinal fluid - a necessary element for his pending kill drug, but the plan backfires when Jason (also Steven Pasquale) is blackmailed by the gang into potentially killing a patient who is a member of an opposing gang.
When a surgery's complications force it to continue after 8:25pm, Jason (Steven Pasquale) chances taking Ruben's (Lin-Manuel Miranda) still-unfinished kill drug to hold Ian (also Steven Pasquale) off long enough to finish the surgery. The surgery is a success, but the drug doesn't last as long as planned and both Lena (Alana De La Garza) and Olivia (Ruta Gedmintas) suffer as a result.
Jason (Steven Pasquale), now aware that he has a son, desperately wants a relationship with him, but Olivia (Ruta Gedmintas) feels it's too dangerous and painful. We learn the backstory of how Jason once saved Olivia from Ian (also Steven Pasquale) and from herself. Meanwhile, both Ruben (Lin-Manuel Miranda) and Lena (Alana De La Garza) start to question Jason's practices.
In a desperate attempt to keep "his" son from Jason (Steven Pasquale), he kidnaps him and hides him from both Jason and Olivia (Ruta Gedmintas). Meanwhile, Ruben (Lin-Manuel Miranda) closes in on the kill drug but isn't sure if he should use it - and, if so, who of Jason or Ian (also Steven Pasquale) he should use it on.
After Jason (Steven Pasquale) collapses in front of Dr. Young (Phylicia Rashad), an MRI reveals Jason has a brain tumor - Jason and Ruben's (Lin-Manuel Miranda) plan has worked, the "tumor" surgery will act as a cover for Ruben's implant to destroy Ian (also Steven Pasquale) once and for all but Lena (Alana De La Garza) may soon discover the truth and put a stop to their plans. Meanwhile, Ian has no intention of going down without a fight and will stop at nothing to save himself.
Jason's (Steven Pasquale) brain surgery is about to begin, a neurotransmitter implant that will "cut out" Ian (also Steven Pasquale) for good, however due to the blackout drug he has taken for years, Jason is immune to the normal anesthetic. A much stronger drug is given to Jason and in the midst of his twilight sleep he flashes back to his childhood and the origin of Ian Price is finally revealed. Meanwhile, Jordan (Michael Esper) and Lena (Alana De La Garza) are on separate tracks to uncover Jason's secrets all of which could prevent the surgery's completion.