Sasha Valentino, a legendary Chicago-based female impersonation performer, passed away on Dec. 26 after a long battle with dementia. She was 40.
Valentino was a nationally known pageant performer, whose titles were many and whose chosen family was extensive.
"Sasha Valentino was an icon and an inspiration to us all in the Trans world," said performer Angelique Munro.
Friends and family remember Valentino as a mentor and example to many, who regularly adopted "children" into her ever-growing family and encouraged them in their goals.
In her own work, Valentino won numerous honors for her performances. She was crowned Miss Black Universe in 1996, Miss Universo Latina, Miss Sweetheart International and Miss Liberty International.
In total, friends estimate that she carried more than 40 titles.
"Sasha was tenacious," said Christian Valentino, who considered Sasha Valentino a mother figure and took on the last name to show it. "In a small pint-sized frame, she packed a punch."
Standing at 5'5", usually in a gown, friends say that Valentino intimidated other performers both with her status as a living legend and a style that was copied time and again.
"She was a trendsetter, an innovator," said Takiya Valentino Wynters, who also saw Valentino as family.
Valentino grew up on the South Side of Chicago and graduated from Christian Fenger High School in 1990. In the early '90s she began performing drag at clubs. In time, she was competing in pageants and doing her own drag shows. Her family was intensely supportive, said Christian Valentino. They came to cheer her on at pageants and took each of her losses and wins to heart.
She performed throughout Chicago over the years, making appearances at Jeffery Pub, Hydrate Chicago, Biology Bar ( now closed ) , Taste Entertainment Center among other venues.
Valentino also competed in contests at Chicago's Baton Show lounge, owned by Jim Flint. She competed 11 times in Flint's national Miss Continental pageant, a title she did not live long enough to secure. She also performed at shows for local promoter Otis Mack and in benefits for LGBT and AIDS charities.
"That was her last pageant that she really wanted to win," said Wynters.
According to friends, Valentino mentored countless young trans women who wanted to break into performing, and she impacted many more by serving as a role model.
Christina Valentino, a performer herself, said that many copied her style, trying to perfect the dance moves and outfits that Valentino pulled off.
But most say, Valentino was one-of-a-kind.
"Whatever she did, she always made sure she was going to be the best at it," said longtime friend Terrell Holman.
She performed at numerous venues in the Chicago area, but also performed at pageants all over the country.
Valentino struggled with dementia at the end of her life. She was released from the hospital recently and passed away in her East Chicago, Ind., home. She was preceded in death by father Raymond Harris. She is survived by her mother Fairstine Harris; her grandmother Lillie Williams; her brother Ramaun ( Vernee ) Harris and sister Keisha ( George ) Williams; along with a large extended birth and chosen family.
Valentino wake held Dec. 31
More than 100 family and friends of Sasha Valentino attended a wake for her Dec. 31 at Barker's Funeral Home on the Far South Side. However, because of her mother's religious beliefs ( she is a Jehovah's Witness ) , all of the print materials and photos were of Sasha in male form, and she was even buried in a suit, not one of her fabulous gowns.
Born Raymond Jermaine Harris on Dec. 21, 1971, Sasha lived her last decades as a female impersonation performer across Chicago and the nation. Those facts were left off the obituary handed out at the funeral home.
Several of Sasha's friends and family spoke to Windy City Times at the wake, about their memories of her.
"I've known Sasha for 15 years," said Finesse, who briefly dated Sasha in the late 1990s. "We kept a bond all these years. I remember her performing at East of the Ryan, the Baton, Miss Continental. She was a loving person. She said 'You control your own destiny.' I remember her as having glamour, and she said you have to have the courage to live your own life, no matter what others think of you."
Stephanie Valentino said Sasha was known as her little sister. "I admired her and looked up to her, even though she was younger," Valentino said. Her mother did accept her, Valentino said, but her religious beliefs influenced how she buried her child.
Tina Thompson has known Sasha for around 30 years, she said, from performing around town together at LaRay, CK's, Baton and Tracks in Atlanta, where Thompson now lives. "She had an international following," Thompson said. "She had glamour, elegance, sophistication, and was professional and always a lady. She was a beautiful girl."
Ruthie Mason, Sasha's great aunt, saw her perform and said she was "beautiful." She said her family accepted Sasha, but because Sasha's mother was in charge of the services, the family just had to accept it. Sasha's cousin Mable Casson said while she did not agree with how the wake was handled, it was the mother's choice.
"Performing is what Sasha wanted to do, [ she ] chose and lived it beautifully. [ She ] moved on up," Mason said.
Sasha's friend Pasion has known her for more than 15 years. She remembers her performances to Toni Braxton songs with fondness. "She was a legendary performer," Pasion said. "One of the greatest."
