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Elena and Jimmy dated in college. She became pregnant after Jimmy completed just one year at Loyola College. He dropped out, they married, and he became a Baltimore City police officer. Over the course of their marriage, they had two children together: Sean and Michael.
Elena and Jimmy's marriage ended due to his infidelity. Elena suspected he was being unfaithful and had him followed by a private investigator. The investigator took photos of Jimmy courting Rhonda and gave them to Elena; Rhonda is not aware that this happened. Elena manipulates Jimmy to agree to give her more child support and alimony than he can afford. She is also protective of her sons and worries that Jimmy is an alcoholic and his parenting skills are lacking. Jimmy brought Bubbles to Sean's soccer game and introduced him to Elena, she was obviously caught off guard. He took the boys to a city market where Stringer Bell also happened to be shopping. Jimmy asked them to play cops and follow Stringer he lost them. When Elena heard this story she was incensed and filed for an emergency order to prevent him from seeing the boys. At the court hearing the judge convinced them to work out arrangements between themselves.
In season two Elena was seen working as a realtor. Nick Sobotka and his girlfriend attend an open house that she has organized. Jimmy tried to initiate a reconciliation with Elena and considerably cleaned up his drinking habits and behavior. The two go on a date and Elena admires this "new Jimmy". They go home together and have sex, which leads Jimmy to believe that they are getting back together. Instead, Elena asks Jimmy to leave first thing in the morning so their sons don't get confused or get their hopes up.
In season three, Elena is established as seriously dating a man named Dennis. They attend an Orioles Baseball game with the McNulty boys and are seated in the front row. Dennis is wearing a suit and spends most of the game talking on a cell phone. Jimmy and Bunk are also at the game, but their seats are in the nosebleed section. Bunk suspects that Dennis is a downtown lawyer due to his appearance and mannerisms.
In season four, Elena saw that Jimmy was becoming more stable as a patrolmen and stated to him that "If I knew you were going to be a grown up, things may have worked differently."
Elena's final appearance in season 5 sees her offer some serious advice to Jimmy following his relapse into alcoholism and being "consumed by the job". She implores him to make his life operate around his family rather than his career, showing some genuine concern for Beadie, who she believes is likely to go through a similar break-up with Jimmy to the one she experienced.