MIAMI — The three Alexander brothers charged with sex trafficking usually exuded only arrogant contempt for the women they assaulted and raped over the course of 20 years, according to court files documenting new sordid details about their “playbook” for luring and drugging victims.

But one 2021 exchange between Oren and and Tal Alexander — luxury real estate brokers in Miami and New York — reveals slight concern over keeping their superstar public image intact.

“Start to think about reputation you want out there,” Oren says to his older brother Tal in one of the conversations transcribed by federal investigators in a letter filed Wednesday by Damian Williams, U.S. Attorney in the Southern District of New York, recommending that a judge not grant bail to the brothers.

“We are on top of the game and only thing can bring us down is some Hoe complaining,” Oren says.

“Understood, did someone complain?” Tal says.

Women did complain, even after being threatened by the brothers to keep quiet, and four filed civil lawsuits against the brothers earlier this year, leading to federal and state sex trafficking and rape charges in Miami and New York City that could land them in prison for the rest of their lives.

Tal, 38, and twins Oren and Alon, 37, were arrested at their Miami Beach homes Wednesday by police, FBI agents and Miami-Dade State Attorney’s Office investigators.

Attorney Evan Torgan, who is representing two victims, told the Miami Herald an additional 40 women, including a dozen from Miami, have come forward with sexual assault and rape allegations, some dating back to the brothers’ teenage years at Dr. Michael M. Krop High School near Aventura. One refrain in the women’s complaints is that the brothers often took turns assaulting them while the others watched or pinned them down.

The brothers’ Miami attorney Joel Denaro said any intimate relations they engaged in were consensual. The brothers are expected to be transferred to the same New York City court that indicted rap mogul Sean “Diddy” Combs and deceased financier Jeffrey Epstein on sex trafficking charges.

Started in high school, feds say

Evidence shows that the Alexander brothers “began engaging in acts of sexual violence, including gang rapes, while still in high school,” the letter states.

“Several of these victims were given alcohol by one of the defendants or other individuals,” prosecutors say, and the victims reported “hearing that individuals involved—including Tal Alexander—talked about the assaults at school, boasting about ‘running train’ on their victims and saying that they wanted to ‘do it again.’”

Oren bragged in the Krop yearbook that “riding my first ‘choo choo’ train” was his most memorable moment from high school.

Parties in the Hamptons, Miami Beach, Mexico

As adults splitting their time between Miami and New York City, and hobnobbing in hotspots for the rich and famous, the brothers’ “serial sexual violence only escalated,” the letter says, as they recruited women to parties and trips to the Hamptons, Miami Beach, Mexico, and other places, or met them at nightclubs or on dating apps and invited them back to their apartments, where the victims often imbibed drugged drinks that impaired “their ability to move, and/or memories. Many victims told the brothers ‘no’ or even screamed while the rapes were happening but the defendants ignored any verbal resistance,” the letter says.

“The Government has spoken to dozens of women who reported being similarly raped by one or more of the Alexander Brothers between 2005 and 2021.”

The Alexander brothers, with other men, planned “imports” of women to a vacation rental in the resort town of Tulum, Mexico, in October, 2016, and discussed splitting costs and which drugs — including the drug G, identified as the date rape drug GHB — to give the women in a “Lions in Tulum” WhatsApp chat discovered by investigators. It’s one of several documented in the letter:

Male-1 (4:17 PM): Going to start collecting for the pot to fly bitches down.

ALON (4:20 PM): There should be a fee per bang and after bang

Male-1 (8:23 PM): Starting to collect venmo for girls flights

OREN (8:23 PM): O yea. What’s the lineup. Need to pick winners.

Male-1 (8:24 PM): Lol. It’s gonna be hard to get girls up to your standard

OREN (8:27 PM): Just warn him ur boys are hungry

TAL (10:23 PM): Girls look fresh

ALON (6:00 PM): I think we should all bring chicks and not rely only on promoter since we never met the girls. We need fun girls with good attitude, I’m sure we all met many recently this summer.

Male-2. I know you know some winners.

Male-1 (6:07 PM): I don’t want anyone being upset if they don’t run a 10 man train

Male-1 (6:12 PM): I just need to handle drugs

TAL (6:12 PM): Yes

Male-1 (6:12 PM): I don’t want X around too much

Male-1 (6:13 PM): Coke, shrooms and G

Male-1 (6:13 PM): X makes the girls wanna chase the fucking party

TAL (1:38 PM): Photographers? Drugs?

Male-1 (1:50 PM): All getting worked on

OREN (3:50 PM): Just trying to make sure I get max returns. Was going to come for that Sunday night tax and make sure all girls make quota

Male-1 (3:50 PM): Lol. The whole $500 dollars on a flight?

OREN (3:50 PM): No free rides under my watch

OREN (3:51 PM): That’s more than most of us ever spent on girls. Just want to make sure we get a good ROI [return on investment].

Over Labor Day weekend 2016, Alon and Oren arranged for two women from Illinois they met on a dating app to fly to their vacation house in the Hamptons for a party. In messages from Oren’s iCloud account they discuss booking flights, and Alon says, “We split and try to orgy then out?” Tal replies, “For sure,” the letter states.

Tal arranged for “hot” women to come to the house with promoters from a chat called “Hampton Hot Chicks,” in an exchange in which the promoter says “I want photos of the girls naked,” and Tal replies, “Lol guys were [sic] going to have a lot of fun.”

During the party, the victim from Illinois told investigators that Oren gave her a cocktail and Alon took her to a bedroom. She said she could not move or speak as Oren raped her, and she woke up later with her bathing suit pulled down around her legs.

A woman from Manhattan told investigators about a disturbing encounter with Tal in the summer of 2011 at the brothers’ Hamptons house.

After she drank half a glass of wine, she felt sick. She remembers being held down by Tal while another man entered the room, and being in another room with Tal and the man and a camcorder. She said she woke up in the grass outside the house with a “physical sensation” of “vaginal penetration.”

The brothers relied on “their power and wealth to identify victims, carry out their sadistic sex trafficking scheme, conceal their sexual violence and prevent victims and witnesses from coming forward” by threatening victims with retaliation, the letter says.

Tal and Oren filed a police report alleging harassment against a woman who said she was assaulted by them, and Tal said he would sue her for defamation.

Another victim said Tal threatened her after she told people he drugged her. After civil lawsuits against the brothers were filed in March, Alon began compiling files on the victims “in an apparent attempt to discredit their accusers,” the letter says.

The brothers flaunted their reputation as playboy jet-setters on social media. They were regulars on the New York Post’s celebrity gossip Page Six and named among New York’s most eligible bachelors by Gotham Magazine in 2014. Oren is married now, and asked a Miami judge at a detention hearing Thursday to allow him to accompany his wife, who is nine months’ pregnant, to the hospital when she goes into labor.

Alon also sold high-end real estate and now works for Kent Security, a private security and crisis management company founded by the brothers’ father, Schlomy Alexander. In 2012, Schlomy helped Tal and Oren sell an Indian Creek Village home for $47 million, a record in Miami-Dade County at the time.

In 2019 the brothers made their most notable deal, the record residential sale of a $240 million midtown Manhattan condominium to billionaire Citadel CEO Ken Griffin, who is now headquartered in Miami.

The U.S. attorney’s letter argues that the brothers should remain detained prior to trial because they are a danger to the community, because the weight of corroborating evidence against them — including sexually explicit photos and videos — is strong, and because their wealth, travel habits — often last minute by private jet or yacht — and frequent trips to visit family in Israel make them a flight risk. As recently as May, Tal and Oren brokered a $14.3 million sale in Bay Harbor Islands.

The Real Deal, a real estate industry publication, first reported that women had sued the Alexanders for sexual assault.

Miami Herald staff writer Jay Weaver contributed to this report.

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