Voight has Sumner stay to handle the bomb while he and company jump into action, now on a race to detain Powell before the bomb detonates. Jay and Lindsay chase him through the building until he heads to the elevator. Meanwhile, the crew spots Powell on a roof nearby awaiting his big moment. Intelligence speeds downtown, locating the van - disguised with blue paint - and calls in the bomb squad to disarm it. There, they also find evidence of a third bomb, likely hidden in a white van near police headquarters and set to go off in half an hour. Halstead and Ruzek enter through the roof. After catching one, they look for his partners and one was dead while the other was loose. In 8:30 PM, Jay and Intelligence are on the hunt for the hospital bombers. It is also determined that Lindsay prefers to keep their relationship purely business because her boss Hank Voight (fatherly figure to Lindsay) doesn't tolerate relationships in the Intelligence Unit. When Lindsay realizes she's out of place, the two instead go to dinner. In Conventions, Halstead accompanies Lindsay to her high school reunion. His interrogation tactics are blunt and tough. As a skilled marksman and a former Ranger he provides the tactical know-how and is often the designated sniper covering for the team when needed. Jay Halstead had been in the Intelligence Unit for a month when the show premieres. He later admits to Upton that he found therapy helpful, though it is not until the season 6 episode Trigger that Halstead speaks at length about how his time overseas affected him, telling Upton that he had learned to deal with his PTSD and not let the past trauma define him. While Will was able to reconcile with him, Jay never did and only discovered after Pat's death that the latter was actually proud of him as well. Therefore he has never spoken to Pat in almost 2 years but still loved him.
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Jay also mentions that Pat didn’t even attend his graduation from the Academy. Neither brother has had a good relationship with their father Pat, as he disapproved of their career choices. It was noted she was dying while Jay was deployed, but he came back to care for her. It was revealed that their mother has passed away from cancer. They are from a blue-collar Irish Catholic background and both brothers attended Catholic school.
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Jay's brother Will, who is a doctor on Chicago Med, mentions that they are third-generation residents of the historically Irish-populated South Side neighborhood of Canaryville. The Halsteads are from Chicago, little is known about their family as neither brother talks much about it.