The Moving Target

When you hear about an attorney who’s flown F-14s, faced down the Crips and Bloods, and prosecuted biker gang members with names like “Danger” and “Monster,” you assume the guy is going to be a steely-eyed Clint Eastwood type. Then Thomas P. O’Brien gets on a Zoom call and he’s self-deprecating and kinetic—cracking jokes about his lack of prowess with technology (“I’m like the lawyer who attended the Zoom court hearing with the cat filter on his face,” he says), and stepping from foot to foot during the 60-minute interview.

“That’s because you can’t hit a moving target,” O’Brien says when the latter is mentioned. 

He’s definitely a moving target. He downplays any special physicality he has, saying he’s possessed of “the typical Irish coordination”; but then there are those F-14s. He dismisses the courtroom stare-downs from various Crips and Bloods he was prosecuting, saying, “Most of the time it’s just mad-dogging. They’re not really angry at prosecutors; they’re angry at people in the neighborhood who come in to testify against them.”

Indeed, when O’Brien joined LA’s hard-core gang division, he quickly learned the lengths to which witnesses would go to avoid testifying. “I remember calling a guy one time. He was in lockup. He was my only witness, knew the killer from the neighborhood. The guy takes the stand. He swears in. I said, ‘Let me ask you the following question—’ and he stands up and points to the defendant and says, ‘That guy over there? He didn’t do it!’”

O’Brien still lives in LA and now practices white-collar criminal defense at Ellis George Cipollone Ross O’Brien Annaguey.

“My good friend Eric George, one of the founders of the firm, we used to have more than our fair share of cocktails and talk about practicing together,” he remembers. “I’d say, ‘Maybe someday.’ Then three years ago I thought, let’s try this. I came over and built a team.” He calls the experience “absolutely rejuvenating.” 

The son of a naval officer who once commanded the USS Constitution, O’Brien swore into the Navy at age 16. He’s since surmounted one challenge after another. On the first day of flight school, the Marine captain instructing the class of some 40-odd newbies made it clear that for most of them, it wasn’t going to happen.

“He said, ‘How many guys here want to fly fighters?’” recalls O’Brien. “‘Put your hands down. Two of you will get it, maybe three.’” 

O’Brien was determined to be one of them. “I really worked hard at it,” he says, of mastering the F-14, and accumulating more than 2,000 hours as a radar intercept officer. “There’s a whole bunch of switches and knobs and buttons, and you’re trying to do intercepts at a closure rate of a thousand miles an hour with two other airplanes. They fly by, you’re upside down; it was really, really, really fun. The camaraderie was great. I loved it. Every day was a challenge.” 

After graduation in 1981, O’Brien deployed twice to the North Arabian Sea with his squadron. He was stationed at Miramar in San Diego. “They filmed Top Gun when we were down there, and they were looking for extras. I filmed one day,” he says. “I tell my kids, ‘If I knew the movie was going to become what it became, I would have done all nine days.’”

In 1987, he transitioned to the Naval Reserve (now Navy Reserve), continuing to fly F-14s at NAS Miramar while starting a two-year stint as a stockbroker (“I was terrible,” he says); then he applied to the University of San Diego School of Law so he could stay in the Naval Reserve and be near his flying buddies. He continued flying all through law school.

During his second year, he got a summer job with the DA’s office in Los Angeles. “It was 1992, the Rodney King riots took place, and the whole city was in turmoil,” he says. It was a terrible time but he fell in love with being a prosecutor. After graduation, he was hired by the San Diego County District Attorney’s office, then he became a deputy DA in LA.

“My first jury trial was a gang murder,” he says. “I don’t remember a lot—I did over 30 murder trials—but I remember getting a conviction. So they moved me into the hard-core gang division pretty quickly.”

Next challenge: assistant U.S. attorney for the Central District of California, the largest district in the country. “We did human trafficking, color-of-law cases, and hate crimes,” O’Brien says. After becoming chief of the criminal division and overseeing the first treason case in the U.S. since World War II, against Adam Gadahn—“He grew up in Orange County,” O’Brien says—he set his sights on becoming U.S. attorney.

“I’m naively thinking, ‘I’ve been a prosecutor my whole life; that should be good enough,’” he recalls. “But it’s really a political position.”

The whole process, he says, takes about a year. “There’s a committee, and you make it known to the committee that you’re interested. There’s a fairly lengthy application to fill out, with references and cases you’ve done, and judges you’ve appeared before, and why you want to do the job. And then there’s an interview process—not just Los Angeles but Washington. … It’s not a very transparent process. You just go through it, and it’s one of those ‘We’ll let you know’ things.”

Then one day he got a phone call that didn’t display the usual 10-digit number; it was all zeros. “That’s weird,” he thought. It was the White House. After background checks and FBI investigations, the next call—again from an all-zero number—was from Kenneth Lee, special assistant to President George W. Bush, telling him, “The president is going to nominate you today to be the next U.S. attorney.” In October 2007, O’Brien was unanimously confirmed by the U.S. Senate. He held the job, which included successfully pressing racketeering charges against the Southern California-based Mongols Motorcycle Club, for just under two years. 

And yes, he met each of the presidents he served under. “Both President Bush and President Obama were very warm,” he says. “And each meeting went on—I am going to estimate—between two and four seconds. Like every other guy who gets the chance, you take the photo anyway. It was a little-boy moment.”

O’Brien now works in white-collar litigation, dealing with matters that have little in common with those of the gang members he charged back in the day. Now, for instance, it’s someone in corporate calling to say they think their CFO is cooking the books and can O’Brien come in and check? 

“We walk in, we do our own mini-investigation—I tend to use [retired] federal agents or my former prosecutors because we know how to build a case, not just by defending them now, but because we prosecuted them back in the day,” he says. “We interview the person, get confessions sometimes, and then it’s up to the board to decide what to do with them. Do you fire the guy? Do you try to get the stolen money returned? Do you go over to law enforcement? It’s like working as a federal prosecutor without the luxury of the badge.”

As for flying? During the COVID-19 pandemic he took his flight physical “for the first time in forever and, surprisingly, passed,” he says. “I’m probably going to be locked up in trials for five months, but I promised myself when I come out, to get back into flying again. Because I love it. I really do.”