Dana Joe Winn FBI

Dana Joe Winn, right, holding flag, and his girlfriend Rachel Pert, wearing a Trump flag as a cape, face federal charges stemming from the Jan. 6 insurrection at the U.S. Capitol. Winn lived in Englewood for several years.

WASHINGTON, D.C. — A former Englewood man and his girlfriend have pleaded guilty to one trespassing charge in connection to the Jan. 6 attack on the U.S. Capitol.

Dana Joe Winn, 45, and Rachael Lynn Pert, 40, both entered a guilty plea for one count of entering and remaining in a restricted building or grounds in federal court on Oct. 4.

They had both also been previously charged with “knowingly parading, demonstrating, or picketing in any of the Capitol Buildings.”

Winn, a 1994 graduate of Lemon Bay High School, now lives in Middleburg, Florida, as does Pert and her two children. The two had lived together prior to a court order compelling them to live separately while facing charges

As part of their plea, Winn and Pert affirmed a statement of offense in Oct. 4 describing their actions on Jan. 6.

“The defendant … unlawfully entered the U.S. Capitol on Jan. 6, 2021,” read the statement.

The document went on to describe that Winn and Pert were photographed inside the Capitol building. Winn was photographed holding an American flag on a pole — placed upside-down to signal distress — while walking with Pert, who wore a “Trump 2020” flag around her shoulders.

The statement also contained quotes from video/audio recordings of the pair after they exited the Capitol:

The two took part in the Jan. 6 “Stop the Steal” rally in support of then-President Donald Trump, who alleged that election fraud was behind his loss to current President Joe Biden in the 2020 election.

The rally was scheduled for the same day that Congress was due to certify the Electoral College results from that election.

Members of the crowd breached the perimeter at the Capitol established by police — in some instances breaking through windows and assaulting Capitol police — and occupied the building for several hours until expelled by law enforcement. The certification process was temporarily delayed by the riot.

Winn and Pert were arrested by the FBI after they returned from Washington D.C., after someone recognized Pert at her job and called the sighting to federal authorities.

The pair had previously told FBI agents that they were at the Capitol, but that “no one instructed them that they could not enter,” according to the FBI’s statement of facts, included in the case filing.

Court documents noted that both Winn and Pert work full-time, but still qualified for court-appointed counsel under the Sixth Amendment.

The sentencing for Winn and Pert is set for Dec. 20. The court granted a motion by the defense to have the sentencing proceedings be done over video conferencing to avoid financial hardship for Winn and Pert, the latter of whom is the primary caretaker for her 10- and 7-year-old children.

“Consequently, it will be a significant financial burden on both defendants if they are required to travel to/from Middleburg, Florida to Washington, D.C.,” read the order granting the motion for video conferencing.


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