Trial attorneys Sam Gregory and Ken Montgomery share their tips at KCCBA meeting

November 25, 2022 Rob Abruzzese

President Darran Winslow (center) and the Kings County Criminal Bar Association hosted Samuel Gregory (left) and Kenneth Montgomery (right) for a CLE on trial strategy. Eagle photo by Robert Abruzzese

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BROOKLYN HEIGHTS — Trial attorneys Samuel Gregory and Kenneth Montgomery stressed the importance of being prepared, watching others, and developing a narrative during their Continuing Legal Education seminar in front of the Kings County Criminal Bar Association on Nov. 17.

The one and a half hour lecture was well attended and held at the Brooklyn Bar Association in Brooklyn Heights. KCCBA President Darran Winslow expressed disbelief that two of the best trial attorneys in Brooklyn are also two of the borough’s best people.

“I could talk about our presenters tonight forever as trial attorneys, but the turnout in the room tonight reflects how respected they are,” Winslow said. “Instead, I’ll say that if being a good person is a necessary component of what we do — these are two of the finest people you will meet. Forget their trial skills, they are better people, and that is reflected in the work they do outside of the practice of law. You are an inspiration to us.”

From left: Christopher “Thief in the Night” Wright, Paul Hirsch, and Andrew Rendeiro. Eagle photo by Robert Abruzzese

After brief opening remarks, the two attorneys began going back and forth throughout the CLE as you might expect a well-seasoned attorney to. Gregory recalled a case he tried nearly 30 years ago, talked about some of the challenges, how he overcame them, and all the while Montgomery picked his brain about how he came to those decisions.

“Our challenge has gotten harder because we live in a pretty pro-prosecution society and trials are getting increasingly harder with technology,” Montgomery said. “You have to approach them differently than when I started. In this profession, you have to get better every chance you get. You don’t just go out there and say to yourself, well this is how I did it last time. You have to bring something unique to it.”

Gregory said that over the years he has tried more and more cases in federal court, where, he says, many of the prosecutors have a better educational background than him and more resources. However, he counterbalances that by being prepared and knowing the case inside out.

Pictured from left: Gary “the Boxer” Farrell, Jonathan Laskin, Samuel Gregory and Luis Hernandez. Eagle photo by Robert Abruzzese

“We’re stepping in to assist people who are in some of the most serious situations that they’ve been in for quite some time,” Montgomery said. “The development of narrative is what we’re there to do.”

In the case Gregory discussed Thursday night, knowing it inside and out, and developing his narrative started with taking his client to lunch one afternoon.

“I’m trying to get the guy to cop out, we’ve met twice and it was a hostile relationship so I suggested we go to lunch,” Gregory said. “We sit down, we start talking, he starts eating with his left hand. Well, the video of the robbery shows that the perpetrator held the gun with his right hand and I realize that I had something here.”

Gregory also explained that even after 38 years as an attorney, that it is important to hone your trial skills, and add strategies to your tool belt. He explained that even to this day he normally goes and watches other attorneys before his own trials.

From left: Stacey Richman, Hon. Michael Farkas, Heather Stepanek, Jay Schwitzman, and Adam Bolotin. Eagle photo by Robert Abruzzese

For Montgomery, the most important aspect of a trial is the narrative. He explained that without a good narrative that shows that the prosecutors might not understand the entire story can really help a case, but a bad narrative makes an attorney look like just another piece of furniture in the courtroom.

“The feds, because they’re so highly prepared, it’s like a military operation with how they approach these cases, and if you don’t find your narrative of what happened beyond them you’re just a part of the process,” Montgomery said. “It’s almost like you are a clerk. Jurors feel that so I have spent a lot of time trying to figure out what really happened. Because usually what the U.S. Attorney is saying, they’re just repeating what the informant said, and the informant is saying what he thinks he needs to say.”

Both attorneys felt like, despite the resources and backgrounds of many prosecutors, a good defense attorney that gets to know their case inside and out can overcome the disadvantage.

Damien Brown and Allana Alexander. Eagle photo by Robert Abruzzese

“If you look at the acquittals in the EDNY and SDNY a high percentage have come from people in this room — not the Bronx, not Manhattan, not Queens, not federal lawyers, but lawyers that came out of this room,” Gregory said. “Chris Wright is like a thief in the night. They should rename him because he just quietly steals acquittals from the government. Gary Farrell is an example of someone who just keeps getting better because he is like a fighter who picks up skills in each battle.”

The Kings County Criminal Bar Association is co-sponsoring a Meet and Greet with U.S. Attorney Breon Peace, from the Eastern District of New York, on Wednesday, November 30. That event is free for KCCBA and Brooklyn Bar Association members. Go to www.BrooklynBar.org for more information on that event.

KCCBA Vice President Arthur Aidala will be honored at the upcoming Brooklyn Bar Association Foundation Annual Dinner at El Caribe in Mill Basin on Monday, December 5. President Winslow encouraged members to show up to that dinner to support Aidala.