Last month, a judge threw out one of six original assault charges - of a forced act of oral sex in 2004 lodged by Lucia Evans against the disgraced movie mogul - due to witness inconsistencies and police misconduct.
On Monday, defense lawyer Ben Brafman asked for the five remaining charges to be dismissed or for the court to hold a hearing to "determine the full extent" of what he called "misconduct."
He suggested a police detective had committed "additional misconduct" involving one Weinstein's accusers, failing to disclose that the two continued to communicate after the alleged assault.
Brafman had already asked in August for the entire case to be thrown out, disclosing emails that allegedly showed his client and the alleged rape victim were in a "long-term, consensual, intimate relationship."
On Monday, he followed up with another extensive court filing and released what he said was a text message, sent by one of the Weinstein accusers, months after the alleged assault in which she seemingly tried to meet up with him.
"Hi! Just wondering if u have any news on whether Harvey will have time to see me before he leaves? x Miriam," she allegedly texted in February 2007.
Brafman complained that police misconduct and perjury committed by Evans "irreparably prejudiced the grand jury" and that messages from another accuser Mimi Haleyi to Weinstein show that any sexual contact was "purely consensual."
He also sought to toss two sexual predator charges, the most serious against Weinstein, on the basis of "constitutionally flawed legal theories and not supported by credible evidence."
The judge dropped the 2004 charge after a detective failed to turn over details from a witness interview, and a draft email from Evans to her husband that exposed further inconsistencies in her account.
As things stand, Weinstein, accused by more than 80 women of sexual misconduct, could still spend the rest of his life in prison if convicted of rape in March 2013 and a forced act of oral sex in 2006.
The 66-year-old was arrested in May. He is at large on a $1 million bail and denies any non-consensual sex.
His arrest and arraignments have led #MeToo campaigners to hope that the twice-married father of five will be put on trial, convicted and sent to prison.
The next hearing is scheduled for December 20.
Brafman, one of the most celebrated criminal defense attorneys in America, helped former IMF boss Dominique Strauss-Kahn escape criminal prosecution for alleged sexual assault in 2011.
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