|“|| You understand that "C.I." does
not mean "crazy individual"?
Raymond "Rondo" Washington is a homeless man who sometimes acts as Jane Rizzoli's CI (confidential informant) through his access to information in the criminal world and the shady parts of town. He constantly tries to flirt with Jane, whom he calls "Vanilla". Rondo also refers to Angela as "Mrs. Vanilla" respectively.
Rondo first appears in "She Works Hard for the Money" as a man that flirts with Jane while in her mother's new "pimp car". When he finds out that she and Frost were cops, he walks away, but not before complimenting Jane again and getting scared off by Frost.
In "Born to Run", Rondo again flirts with Jane so her brother, Frankie, who once arrested him, taunts him. Rondo gives Jane a paper with tips of criminal activities and offers to be her CI, but she turns him away. Later, though, he comes through when he steps up as a witness to the shooting of the second victim in the Massachusetts marathon, not realizing that the girl he was checking out may have in fact been the killer. Jane realizes this and gives Rondo money to be her informal CI.
Jane contacts Rondo again in "My Own Worst Enemy" when a victim is killed in what appears to be a mugging in a bad part of the city. She hands him money so that he can keep an eye out for a junkie who could possibly be the killer. Unsatisfied, he has Jane add more cash. He later informs the detectives about Viper and how he could have gotten possession of his heroin.
Rondo reappears in "This Is How a Heart Breaks", claiming to have a C.I. of his own that knows who the killer is. He then directs Jane to Lance Corporal Justin Brown, his source who was once a marine special ops with the victim in Iraq, who answers to "General Rondo". Rondo tells Justin to trust "private Jane" and tells him that she works for him; Jane goes along with him. Jane ends up not believing them as Justin does not seem to be in his right mind, but she pays him to keep looking. Rondo comments about how little Jane pays him, but Rondo offers the money to Justin, instead.
He later shows up at the precinct with another one of his CIs, "Sour Grapes". When his CI sounds crazy to Jane again, he makes some sense out of his information, pointing them to a neighborhood watch volunteer who looks and acts like a pope and drives a popemobile. Later, he tracks down the man himself and stands up to him, engaging him in a fight that does not work well for him.
Also, it is revealed by Angela Rizzoli that Rondo is in fact Raymond Washington, a singer who performed blues with his friend, "Sour Grapes". They used to perform at the Beehive in Boston, where Angela and Frank used to go.
In "Welcome to the Dollhouse", Rondo is at the Division One Cafe, receiving his regular stock of free food from Angela, whom she calls "Mrs. Vanilla". It turns out, the food is for him and his other homeless friends. Later, after seeing Angela's blog post about needing help on Jane's case, he forms their little group called "Angela's Guardians" and sends out his homeless friends to ride buses and look out for the young women that the doll killer might be targeting. He later makes a statement when the group is interviewed on television.
Jane contacts him again in "Melt My Heart to Stone" and once again proves helpful when he is able to name their victim, but only after Jane flashes him some money. He also has one of his prostitute friends, Kitty, give them information.
Rondo has been shown to have a comical character persona.