Winner was born in Texas to Billie and Ronald Winner. Her unusual name was chosen by her father. She grew up in Kingsville, Texas, and attended H. M. King High School, where she learned Latin at school, studied Arabic in her free time, and played on the soccer and tennis teams.
Her father's influence early in her life had extensively shaped Winner's world view on many topics, including politics, history, philosophy, and religion. After the September 11 attacks, Winner had intense discussions with her father on geopolitics and Islam and she decided to learn the Arabic language.
When FBI agents arrived at her home on June 3, 2017, Winner did not insist on consulting a lawyer, and the FBI agents failed to inform her of her Miranda rights when Winner was arrested. When her house was searched and she was initially questioned, Winner stated that she wasn't "trying to be a Snowden or anything".
Winner was charged with "removing classified material from a government facility and mailing it to a news outlet." On June 8, 2017, she pleaded not guilty to a charge of "willful retention and transmission of national defense information" and was denied bail. Prosecutors alleged she may have been involved in other leaks of classified information, and might try to flee the country if released. Justice Department lawyers also argued that her defense team should not be allowed to discuss any classified information, even if it was in news reports published by the media.
On August 29, 2017, Winner's attorneys filed a motion in district court to suppress her statements to law enforcement, arguing that Winner was not read her Miranda rights before being interrogated by the FBI on June 3. On October 5, 2017, Epps denied a second request from her defense attorneys that bail be set. In December 2017, The Intercept reported that Winner's defense team was allowed to discuss the case with her, including its classified aspects, in a Sensitive Compartmented Information Facility (SCIF). First Look, the parent company of The Intercept, helped fund her defense, and as of September 2020[update] was still paying her legal bills.
On June 21, 2018, Winner asked the court to allow her to change her plea to guilty. On June 26, she pleaded guilty to one count of felony transmission of national defense information. Winner's plea agreement with prosecutors called for her to serve five years and three months in prison followed by three years of supervised release. No one has ever received a longer sentence for leaking classified information to a media outlet.
On August 23, 2018, Winner was sentenced to the agreed-upon five years and three months in prison for violating the Espionage Act of 1917. Prosecutors said her sentence, 63 months in prison, was the longest ever imposed in federal court for an unauthorized release of government information to the media. At her sentencing, Winner told the judge, "My actions were a cruel betrayal of my nation's trust in me." The New York Times reported, "Under the plea agreement, Ms. Winner will be transferred to the Federal Bureau of Prisons Federal Medical Center, Carswell in Fort Worth, Texas, where she can receive treatment for bulimia and be relatively close to her family."
On April 24, 2020, a federal judge rejected Winner's request to commute the remaining 19 months of her 63-month sentence and be released to home confinement due to the COVID-19 pandemic. Winner's lawyer argued that her history of respiratory illness and immune system compromised by bulimia makes her highly vulnerable to the virus. Two inmates had tested positive before Winner was transferred to the federal medical center where, under the terms of her June 2018 guilty plea agreement, Winner was housed to meet her special needs. She was immediately quarantined and never entered the general population there. The government insisted that the Bureau of Prisons (BOP) "has taken aggressive action to mitigate the danger and is taking careful steps to protect inmates' and BOP staff members' health." The judge found that Winner did not exhaust her administrative remedies through the BOP, which he held has sole authority to grant her compassionate release. Winner tested positive for COVID-19 in July 2020. By September 13, 2020, Winner was recovering from the coronavirus, although still experiencing occasional shortness of breath.
On June 2, 2021, Winner was transferred from prison to a transitional facility, the San Antonio, Texas, Residential Reentry Management center. According to Alison Grinter Allen, Winner's lawyer, she left prison early as a result of "good behavior" while inside, and not because of compassionate release.
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