The explosion of social media and the resulting ease of sharing photographs online have created a host of novel legal questions. For Richard Liebowitz, a photographer turned New York attorney, it's been a business opportunity.

In the three years his boutique firm has been open, he has sued just about every major media company — CBS, Vice, Yahoo, iHeartMedia and The Hollywood Reporter parent Prometheus Global Media, to name a few — for copyright infringement on behalf of more than 350 photographers.

"It's very tough to make a living as a photographer," he says. "My goal is ultimately to get them paid for their work so they can focus on taking pictures."

Liebowitz, 29, won't say how many lawsuits he's brought against media firms, but searches of federal court records show hundreds of filings. "It's a major problem in the digital age," he says. "It's so easy to take without permission."

But intellectual property experts have criticized this kind of niche practice — especially the breakneck rate at which he files complaints. "In one sense, it feels like a nuisance," says L.A.-based IP lawyer Jesse Saivar. “But, in the other sense, the attorneys that bring these cases would argue they’re doing a greater good and are enforcing the laws that are there for a reason.”

In one of more than three dozen cases filed on behalf of photographer Steve Sands, Liebowitz sued Meredith Corp. over its alleged unauthorized use of a photograph of Benedict Cumberbatch as his Marvel character Dr. Strange in a Hello Giggles web story. He's seeking $150,000 in damages, the maximum allowed under the law for willful infringement of a copyrighted work.

While photos often can be licensed for as little as tens or hundreds of dollars, the statute provides up to $30,000 in damages for even non-willful unauthorized use. Although Liebowitz won't dish on specifics, he says most of his cases settle, and while the number of zeroes on settlement checks can vary, the payout is typically higher than the standard license fee.

"No media company is safe," says entertainment litigator James Sammataro. "The defendants are a who's who of established media companies, demonstrating that even with the most prudent clearance standards, certain works may inevitably escape detection."

Liebowitz isn't fazed by criticism from some that he's the intellectual property equivalent of an ambulance chaser. "Theft is theft," he says. But at least one Manhattan federal judge has noticed the volume of his cases.

"Plaintiff's counsel, Richard Liebowitz, is a known copyright 'troll,' filing over 500 cases in this district alone in the past twenty-four months," wrote U.S. District Judge Denise Cote in a Feb. 22 ruling on a motion for fees. The next week, in a different case, Cote sanctioned him $10,000 for failing to serve proper notice of a pretrial conference. She later reduced the fine to $2,000 and ordered him to complete ethics and professionalism training.

Liebowitz isn't the only IP attorney who's caught the attention of others in the field for filing cases en masse. Stephen Doniger of Venice, California-based Doniger/Burroughs proudly notes that he and his colleagues handle more copyright cases than any other firm the country.

"It's a good fight to be fighting, and there's a big concern that overzealous attorneys who don't necessarily know what they're doing could hurt the effort," he says. "The difference between us and everyone else is we take cases to trial, and we have a great track record. We've never lost one and we consistently get big, six-figure verdicts." (Doniger, who also reps fashion clients in copyright cases, won an almost $850,000 jury verdict against H&M in December.)

Saivar contends that the incentives created by current copyright statutes are to blame for mass litigation tactics. "There should never be motivation to file a lawsuit over something whose actual damages is so low," he says. "There's no reason not to file the suit because you could potentially get statutory damages and attorneys' fees."

With a recent trend of suing celebrities for posting paparazzi images of themselves on Instagram — and a decision that could cause embedding tweets to constitute infringement — the number of potential plaintiffs could soon skyrocket.

Technology is also making it easier to send warning letters, according to Saivar, who routinely responds to demand letters on behalf of e-commerce clients and says some attorneys seem to have automated the process.

“They get an email that says ‘You infringed our client’s copyrighted image, you didn’t have a license to do it, click on this button to pay the $1,200 license,'” he says. “That’s when it really blew my mind, when I started seeing click-to-pay buttons. Obviously, if you’re doing that, you’re sending out a million of these.”

Liebowitz isn’t employing that tactic currently, but he also doesn’t see anything wrong with it. “Ultimately, if the letter outlines what happened in that particular case and they want to pay quickly, that’s a solution,” he says. “That’s an interesting tool to try to get people to pay.” 

Industry experts have suggested that these kinds of cases show a need for a small claims court within the U.S. Copyright Office.

“Ironically, the genesis for a copyright small claims court was to protect plaintiffs who may be dissuaded from filing an expensive lawsuit in which they could only anticipate a modest recovery,” says Sammataro. “Scouring the dockets suggest that it is defendants who may be best served.”

Doniger disagrees, and says it's actually the volume of cases that aren't being filed that demonstrates a need for such a court. "I’m not going to be filing cases over one or two photos that have not been registered with the U.S. Copyright Office," he says. "There are so many legitimate claims like that, and there is no recourse for the photographer. No attorney is going to handle a case where there’s no timely registration."

As for Liebowitz, he sees the embedding decision as a major win for photographers and the digital landscape as one full of opportunity.

"I think social media law in general related to copyright is going to be a growing field in coming years," Liebowitz says. "Right now, we are a niche practice, but we hope to grow just like any business."

A version of this story first appeared in the April 4 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.