The actor known for his comedy roles was once Olivia Benson’s ex-boyfriend and a member of SVU’s elite squad.

When reminiscing about the early seasons of Law & Order: Special Victims Unit, it’s hard to forget the lovable Detective Brian Cassidy, played by Dean Winters.

Cassidy’s charm was undeniable during Winters’ initial season with SVU, though he was the first detective to ever leave the Manhattan SVU. However, he stole the heart of Captain Olivia Benson (Mariska Hargitay) after his return to SVU more than a decade after his initial departure.

Cassidy may have left the chaos of the squad, but Law & Order fans will always remember the passion he brought to each case.

Detective Brian Cassidy (Dean Winters) appears in Law & Order: Special Victims Unit Season 19 Episode 14. Photo: Michael Parmelee/NBC

When did Brian Cassidy first appear on Law & Order: SVU?

Cassidy was a member of Law & Order: SVU‘s debut cast, appearing in the pilot episode (“Payback”) and throughout Season 1.

It was during this era that Cassidy and Benson had a one-night stand and, while they would later explore a serious relationship, she kept her focus on work. He openly wanted more from her, but Benson turned him down because they worked together.

Despite being the squad’s class clown, Cassidy soon established himself as a dedicated and earnest detective. His lack of experience on the force inspired his pair-up with the seasoned veteran of the squad, Detective John Munch (Richard Belzer).

Detective Brian Cassidy (Dean Winters), Captain Donald Cragen (Dann Florek), Detective Olivia Benson (Mariska Hargitay), Detective Elliot Stabler (Christopher Meloni), Detective Monique Jefferies (Michelle Hurd), and Detective John Munch (Richard Belzer) appear in Law & Order: Special Victims Unit Season 1. Photo: Chris Haston/NBCU Photo Bank

Why did Dean Winters leave SVU after playing Brian Cassidy for one season?

Cassidy was valuable in several cases but often struggled to cope with the grueling nature of sex crimes, especially those involving minors.

Despite Cassidy having a hand in several arrests in SVU‘s first season, former Captain Donald Cragen (Dann Florek) quickly clocked his incompatibility for the role. He then assigned Cassidy a simple task: Go check on one of the assault survivors.

After realizing he lacked the stomach to handle the day-to-day testimonies of the victims whose cases he was investigating, Cassidy transferred to NYPD’s Narcotics Division in Season 1, Episode 13 (“Disrobed”).

Detective Brian Cassidy (Dean Winters), Detective John Munch (Richard Belzer), Detective Olivia Benson (Mariska Hargitay), and Marta Stevens (Mili Avital) appear in Law & Order: Special Victims Unit Season 1 Episode 1. Photo: Jessica Burstein/NBC

When did Dean Winters return to SVU as Brian Cassidy?

Winters first reprised his role as Cassidy in the Season 13 finale (“Rhodium Nights”).

During his time away from the SVU, Cassidy had soared through the ranks of the NYPD, eventually becoming an undercover detective. While investigating a pimp, Benson and her then-partner Nick Amaro (Danny Pino) crossed paths with Cassidy, who had been working undercover for three years disguised as the pimp’s bodyguard. His case became entangled with the SVU’s investigation.

Benson learned in the course of their shared investigation that Cassidy had matured tremendously in his time away from the squad, and had become more confident as an investigator.

Cassidy remained part of the show through Season 14 and Season 15, as he and Benson got a second chance at romance.

Detective Olivia Benson (Mariska Hargitay) and Detective Brian Cassidy (Dean Winters) appear in Law & Order: Special Victims Unit Season 20 Episode 16. Photo: Peter Kramer/NBC

What happened between Brian Cassidy and Olivia Benson on SVU?

The two detectives became involved in a serious relationship in Season 14, following their Season 1 one-night stand.

In Season 14 Episode 2 (“Above Suspicion”), Cassidy’s cover as the pimp’s bodyguard was blown and he got shot.

He was seriously wounded and rushed to the hospital while Amaro and Benson cleaned up the mess. When Cassidy awoke in the hospital, Benson was there to greet him, telling him she wasn’t the same person she was the first time they worked together.

She then kissed him.

Their romance were confirmed in Season 14, Episode 3 (“Undercover Blue”), albeit in less-than-ideal circumstances after Munch and Amaro arrived at Cassidy’s apartment to inform him that he had been accused of a sexual assault.

The accuser was a sex worker with whom Cassidy used to have a consensual relationship during his time undercover. While her colleagues were delivering the news, Benson walked out of Cassidy’s bedroom in a nightshirt.

The accusations complicated their romance, but the charges were dropped after it came to light that the woman had made a false accusation in order to sue the NYPD. Still, as a result of the consensual relationship, Cassidy was demoted.

Despite the demotion, he and Benson continued their relationship, dating throughout Season 14 and Season 15.

After Benson was traumatically kidnapped and tortured by the serial killer William Lewis (Pablo Schreiber) in Season 14, it was Cassidy who became her shoulder to cry on.

In Season 15 of SVU, the couple moved in together.

Detective Brian Cassidy (Dean Winters) and Detective Olivia Benson (Mariska Hargitay) appear in Law & Order: Special Victims Unit Season 14 Episode 7. Photo: Michael Parmelee/NBC

Why did Brian Cassidy leave SVU in Season 15?

After Cassidy and Benson because a couple, their compatibility remained in question. She was a meticulous planner, never running into the action without thinking of the situation from all angles. On the other hand, he was impulsive and short-sighted. Their differences caused tension for the couple at several points during their relationship, especially when the topic of their futures came up.

In Season 15, Episode 19 (“Downloaded Child”), Benson ended things between her and Cassidy after concluding that they would always be fundamentally different people. The break-up was amicable, and it was clear she would always hold a special place in his heart.

Dean Winter’s Guest Appearances on Law & Order: SVU 

Detective Brian Cassidy (Dean Winters) appears in Law & Order: Special Victims Unit, Season 20 Episode 16. Photo: Peter Kramer/NBC

Winters reprised his role as Cassidy in Season 19 and Season 20 of SVU.

In the Season 19 premiere (“Gone Fishin'”), Cassidy returned as an investigator for the district attorney’s office, informing Benson that he was investigating  allegations that she was abusing her adopted son, Noah (Ryan Buggle). Though he ultimately cleared her in Episode 2 (“Mood”), she was furious over his role and told him she never wanted to speak to him again.

In Season 19, Episode 14 (“Chasing Demons”), Cassidy was asked to testify against a child molester whom he’d physically assaulted during the arrest. During his testimony, he threatened to kill the defendant, leading to a mistrial.

After the defendant was found dead the following day, Cassidy became the prime suspect. During the subsequent investigation, he was cleared, but eventually confessed that his passion on the stand was because he was molested as a child by his Little League coach.

Later in that episode, he and Benson reconciled after he apologized for complicating her custody of Noah.

What was Dean Winters’ last episode of SVU as Brian Cassidy?

Cassidy finally got justice for himself in Season 20, Episode 16 (“Facing Demons”), after a suicide led the SVU to Cassidy’s abuser.

Upon finding photos of Cassidy as a child in the defendant’s home, the squad asked him to testify. Despite having no wish to rehash his childhood trauma in court, he agreed once he learned that no other survivors were able to step forward.

With Benson and the squad’s support, Cassidy’s agreement to testify led to his abuser’s arrest.

It was his last appearance (so far!) on the show.

Counselor Barry Querns (Reg E Cathey) and Detective Brian Cassidy (Dean Winters) appear in Law & Order: Special Victims Unit Season 14 Episode 7. Photo: Michael Parmelee/NBCIn Season 19, Episode 14 (“Chasing Demons”), Cassidy was asked to testify against a child molester whom he’d physically assaulted during the arrest. During his testimony, he threatened to kill the defendant, leading to a mistrial.

After the defendant was found dead the following day, Cassidy became the prime suspect. During the subsequent investigation, he was cleared, but eventually confessed that his passion on the stand was because he was molested as a child by his Little League coach.

Later in that episode, he and Benson reconciled after he apologized for complicating her custody of Noah.

What was Dean Winters’ last episode of SVU as Brian Cassidy?

Cassidy finally got justice for himself in Season 20, Episode 16 (“Facing Demons”), after a suicide led the SVU to Cassidy’s abuser.

Upon finding photos of Cassidy as a child in the defendant’s home, the squad asked him to testify. Despite having no wish to rehash his childhood trauma in court, he agreed once he learned that no other survivors were able to step forward.

With Benson and the squad’s support, Cassidy’s agreement to testify led to his abuser’s arrest.

It was his last appearance (so far!) on the show.

Counselor Barry Querns (Reg E Cathey) and Detective Brian Cassidy (Dean Winters) appear in Law & Order: Special Victims Unit Season 14 Episode 7. Photo: Michael Parmelee/NBC