The “Asshole Awards”: Inside the Alexanders’ defense strategy

An attorney for Tal Alexander stood before a jury in late January and painted an image of his and his brothers’ lifestyle that would make jurors cringe.

In their early 20s, they were party boys. Womanizers.

“They slept with many, many women,” said Deanna Paul during her opening arguments, describing the way they talked about women as “arrogant” and “crude.”

If the jury was there for the “asshole awards,” this would be an easy case, she said.

Teny Geragos, an attorney representing Oren months after successfully defending Sean “Diddy” Combs against sex trafficking charges, told the jury that they’ll find Oren was a playboy, “out to have as much sex as possible with as many women as he could.” But that behavior, maybe immoral to some, “is not criminal,” said Geragos.

The opening statements grounded what attorneys for the brothers have had to face head-on, early: seeking out sex was part of their lifestyles at the time. They took full advantage of New York City nightlife, with drugs and alcohol in tow, and they had cash to spend pursuing that lifestyle in other hotspots. They surrounded themselves with women who were attracted to their resources. But the government has gone too far in trying to cast them as criminals for that lifestyle, the defense has said.

Prosecutors say they, along with other men, drugged and raped women between 2008 and 2021 in New York, Aspen, Tulum and other luxury destinations. The brothers have denied the allegations and pleaded not guilty. They’re facing a dozen charges tied to sex trafficking, many of which are broad allegations that encompass alleged incidents of rape, including with underage victims.

Each brother faces up to life in prison, with a mandatory minimum sentence of 15 years if convicted of conspiracy.

In the first three weeks of trial for Oren, Alon and Tal Alexander, their attorneys have tried to sow doubt and create distance from the most severe charges, and even from each other, said Mitchell Epner, a former federal prosecutor.

“If these defendants are convicted, they are looking at the real possibility of life,” Epner said. “So [you] could imagine that part of the mitigation strategy is to say, ‘even if I am guilty of some things, I’m not guilty of the worst and not as many of them as other people.’”

The cross-examinations have shed light on how the Alexanders’ attorneys will likely present their case in the coming weeks of the trial. While the team is largely relying on its questioning of alleged victims to make their case, documents filed with the court indicate the defense is planning to call expert witnesses aimed at refuting some of the testimony proffered by the government.

Attorneys for the brothers have sought to cast their encounters with witnesses who accuse them of rape as part and parcel with the dating scene for 20-somethings. Those encounters, they say, were consensual and ended with disappointed women who have resurfaced years later for attention or money from wealthy scions of luxury real estate, the same trappings that attracted them in the first place.

The attorneys have spent hours questioning victims, prodding them on inconsistencies in their accounts and their actions leading up to and following the alleged attacks. They’ve pressed them on if they knew of Oren and Tal’s rising careers in luxury real estate, and if, along with Alon, that they were sons of a wealthy South Florida spec developer. They’ve grilled women about hiring civil attorneys and why they filed lawsuits against the brothers (Only two of the alleged victims who have testified so far filed lawsuits.)

Jason Goldman, an attorney who has represented the brothers in civil suits and previously in the criminal case, declined to comment on their strategy, calling it premature and inappropriate midway through the trial.

“What has been clear throughout the proceedings is the defense’s position: our clients did not drug anyone, did not rape or assault anyone, and there is no reliable evidence that will demonstrate otherwise,” he said in a statement. “We will continue to address the case through the evidence presented in court.”

Challenging a “mountain” of evidence

Each brother has his own team of high-powered lawyers, but their approach in the courtroom has been similar.

So far, nine women testified about being sexually assaulted by one or more of the Alexanders. Many of them have described feeling like they were losing control of their bodies after consuming a drink in the company of one or more of the brothers.

The testimony has been emotional, with compelling evidence. One woman who said she witnessed a rape during a weekend trip to the Hamptons said she used her eyeliner to write “Rapists!” on a door before leaving the house the day after, which was shown in an image presented by prosecutors to the court. Prosecutors showed her the photograph, which was found on Tal’s iCloud account. Prosecutors also showed the jury a video allegedly showing Oren and another man raping a woman who was 17 years old at the time, which they found on a hard drive in Tal’s Manhattan apartment.

Group chats and text messages in evidence show how the brothers and their friends secured drugs such as ketamine, MDMA and GHB for trips, including at least one where a woman has alleged she was drugged and assaulted.

Prosecutors have well over a dozen more alleged victims who can testify, but Judge Valerie Caproni has said she would likely cap how many women take the stand.

With the lion’s share of prosecutors’ evidence focused on victim testimony, Geragos — the daughter of famed criminal defense attorney Mark Geragos — urged jurors in her opening arguments to take note of the lack of contemporaneous police reports or toxicology reports backing victims’ claims of drugging.

The prosecution argued through expert testimony from Dr. Stacey Hail that health care providers often don’t perform toxicology testing. Hail also said that GHB is an “excellent choice” for such assaults because of testing challenges.

Michelle Simpson Tuegel, an attorney who is not involved in the case but who has represented survivors of sexual assault, said the gaps in evidence are common in sexual assault cases, and the combination of testimony and text messages and photos presented by the prosecution means the defense is “up against a mountain.”

“That [prosecutors] found a photo that matched that from the hard drive of the Alexander brothers… You don’t have things like that in every case,” said Simpson Tuegel, who has represented victims in cases that include the Larry Nassar investigation.

“People talk about sexual assault cases and how there’s not corroborating evidence. I know that doesn’t prove it happened to a given person on a given day, but it’s very corroborative of the culture and what was going on and what women were experiencing,” she said.

Questions of memory

About a week into the trial, a woman using the pseudonym Bela Koval told the jury she was raped by Oren in the Hamptons in 2016. In an account that echoed several others included in the case, she described accepting a drink from him at a party and taking a few sips before beginning to lose control of her limbs. Her memory of the rest of the night is fragmented, but she said one event remains clear: Oren raping her while she couldn’t move or fight him off.

Hers was among the striking accounts that attorneys for the brothers braced the jury for in their opening statements.

“This has taken such an emotional toll on me,” Koval said. “I finally would like the brothers to have accountability for what they did to me and what they did for [sic] other women.”

What followed was a grueling, hours-long cross-examination led by Geragos, who grilled Koval on differences between the details she first shared with the government and what she later said in the courtroom.

“You testified yesterday to several things that are absolutely different than the story that you first told the government for approximately a year and a half, isn’t that right?” Geragos asked before picking apart specifics of Koval’s account, including her recollection of the outfit she was wearing when she was assaulted.

“The most important parts, that I was raped, that I was drugged, and the sequence of my events have never changed,” Koval replied. “Insignificant little details may have changed… I can’t really remember what I was wearing or if I made a quick change 10 years ago.”

Geragos’ questioning turned rapid-fire, pushing Koval on her memory of the alleged assault. But the heightened exchanges didn’t always land.

“Because you’re not sure about a lot of things that happened that night, you said, right?” Geragos asked after prodding Koval about the assault.

“Don’t do that,” Caproni said, interjecting from her bench. “Ask a question.”

Attorneys for the Alexanders have also repeatedly questioned alleged victims about their alcohol and drug use and why they didn’t report their attacks to law enforcement or seek medical attention at the time.

Several of the alleged victims have testified that they traded messages with one or more of the Alexander brothers after their assaults. One woman, testifying under the pseudonym Maya Miller, said she texted Tal days after she alleges he raped her in the shower of a Hamptons home, including that she was having a “fucking amazing time” in Manhattan.

“At this time, I was so hurt for what had happened to me, that I was trying hard. I wanted answers, I wanted some relief,” Miller said. “This is how I reacted to my trauma.”

Poking holes in the “conspiracy”

The government’s 12-count indictment charges all three of the brothers with conspiracy to commit sex trafficking, but individual allegations name different combinations of brothers to allege sex trafficking by force, fraud or coercion; and inducement to travel to engage in unlawful sexual activity. Those charges carry minimum mandatory 10-year sentences.

To undercut prosecutors’ conspiracy claims, the Alexanders’ attorneys have also pressed alleged victims on which brother, if any, asked them to travel or attend to an event, handed them a drink or was present during the alleged attack.

The defense team’s efforts to establish each brother’s distinct role in the allegations is particularly relevant for Tal, who Paul argued is being “carried along like a current” with his twin brothers.

“The government is counting on that,” Paul said during her opening statements. “[Prosecutors] just told you a broad dark picture that allows you to view these three brothers as monsters, and it makes it easier for you to judge these men collectively, rather than looking at them as individuals.”

Paul also argued that of the six sex trafficking charges Tal is facing, three of the alleged victims “don’t accuse him of anything.”

“Not of inviting them, not of assaulting them, not of offering them anything in exchange for sex,” Paul said. “The government has simply included him in these sex trafficking counts by women who do not accuse him of anything.”

In at least one case, the defense team’s line of questioning revealed a discrepancy that could come in handy. While on the stand, Alon’s attorney, Howard Srebnick, asked a woman using the pseudonym Isa Brooks to identify several people in a series of photographs from Memorial Day weekend in 2009, when Brooks alleges she was raped in the Hamptons by Tal, Alon and two other men. In one of the photographs, Brooks identified a man as Alon, though it was, according to Srebnick, actually Oren.

“Do you remember telling the government in 2025, last year, that you know his name to be Alon Alexander now, but don’t know if you knew the name at the time,” Srebnick asked. Brooks replied that she wasn’t sure if that’s what she told the government.

Assistant U.S. Attorney Madison Smyser later asked Brooks why she believed it was Alon who raped her, alongside Tal and the two other men.

“I observed the difference in character and demeanor and the way they looked, so I knew it was the twin that was a little bit more shy and quiet,” Brooks said.

“Were you in a better position to identify them back then than you are today?” Smyser asked.

“Yes,” Brooks replied.

Ellen Cranley contributed reporting.