It was one of three trips to Chicago that McDermott made between March 11 and March 26 as he conversed through text messages with someone with Mexican telephone numbers, court documents say.

Agents said McDermott delivered drugs to a man in Edgewood, who then drove into Baltimore. The Edgewood man, Philip Wheeler, picked up cash from the proceeds — as much as $300,000 — and was told to take $50,000 for himself, according to documents.

On a different date, after observing what they believed to be a transaction in Charles Town, W.Va., authorities pulled over an alleged Brooks associate named James "Country" Bryant in Baltimore County. They found two bricks of heroin inside his truck, according to the complaint filed in court.

McDermott's attorney, Joseph Murtha, said he did not have enough information to comment on the allegations, as did the attorneys for Wilson and Wheeler. Bryant did not have an attorney listed. Each faces a charge of conspiracy to distribute a kilogram or more of heroin, which carries a minimum of 10 years in federal prison and a maximum of life.

A task force officer, Brian Shutt, also arrested two Illinois men after observing them outside a Pikesville apartment where a payoff was supposed to take place. The agents found tens of thousands of dollars in cash stuffed into pipes inside a truck, according to court records.

Meanwhile in New Orleans, investigators were tracking Brooks as well. They say for the past two years, he had been conspiring with couriers to bring in three to five kilograms per delivery, about once per month, making drops in Jefferson Parish, west of New Orleans.

He would send in couriers or sometimes travel himself to pick up cash, which he referred to as "documents," according to a complaint filed in the Eastern District of Texas.

Brooks had known or at least suspected that he was under surveillance, telling Wilson, his Pikesville associate, that he believed someone had turned on him.

"I ... figured out where the um, my issue, is coming from," he told Wilson.

In a recorded conversation detailed in court records, he told an associate a day before his arrest that his lawyer said he was facing "a dime" — 10 years in prison.

"Maybe I can get it down to a nickel," he said optimistically, according to the records.

Maryland authorities are looking to seize more than $600,000 in cash taken from properties in Pikesville and Randallstown, as well as several vehicles, including a Freightliner tractor-trailer belonging to Bryant.