A Skadden Veteran's Uneasy Take on Smarter Machines

David Goldschmidt retired last month after a 37-year career at Skadden, Arps, Slate, Meagher & Flom, ending a tenure that made him a rare constant in an industry increasingly defined by churn. While he stayed put, the ground beneath him did not. From his perch at the fourth-highest-grossing law firm in the country, Goldschmidt worked through a technological revolution that shifted the legal industry from analog to algorithmic.

He's not convinced smarter machines make for better lawyers. The veteran capital markets partner, who guided companies through some of history's largest IPOs, now questions whether artificial intelligence can replicate the intellectual struggle that forged generations of legal professionals.

Three years out of law school in 1990, David Goldschmidt landed the kind of assignment most young corporate lawyers only dream of: taking a company public. When a senior partner at the venerated New York law firm told him to "run with" biotech company Regeneron's IPO, his career changed. Goldschmidt sweated his way through writing the prospectus, translating the company's scientific ambitions into plain language for investors.

Regeneron raised twice the expected amount in the initial offering, but the victory was volatile. The stock swung sharply after the IPO, prompting shareholder lawsuits. A federal judge dismissed the cases against Regeneron, finding the company's disclosures to be accurate and legally sufficient. For Goldschmidt, the trial by fire taught him something fundamental.

"I could do this," he remembers thinking.

That moment of self-discovery launched a trajectory that would see Goldschmidt rise through the ranks to become a partner and, eventually, the global head of Skadden's capital markets practice. His name appeared routinely on the opening pages of S-1 filings, including those of Casper, Match Group, and Rivian Automotive, whose $12 billion raise was one of the largest US IPOs in history.

Goldschmidt's journey began with a deliberate avoidance of Big Law. He started at the smaller, white-shoe firm Breed, Abbott & Morgan, driven by a curiosity about "how the markets work" rather than a desire for corporate prestige. His first day in the New York office coincided with October 19, 1987—Black Monday—when the Dow Jones Industrial Average plunged more than 500 points.

As an HR representative led him through partner introductions, the mood darkened with each knock. One partner cut in: "How do you think I'm doing? The market's down 22%." The crash wiped out roughly half a trillion dollars in market value, but the violence was brief. Leveraged buyouts and mergers soon exploded, translating into enormous amounts of work for law firms.

Goldschmidt realized the "genteel" lifestyle he had sought was an illusion. "Regardless of what size law firm you work at, you're going to work hard," he said. Within his first year, he left to join Skadden's capital markets practice, securing a front-row seat to the global economy that he would occupy for the next 37 years.

He fell in love with the fervor of the environment and the people hustling beside him. In 2025 alone, the hundred-person Skadden group handled more than $300 billion worth of transactions, cementing the firm's position as a powerhouse in capital markets.

The intensity of the work hasn't changed, but the work itself has. When Goldschmidt started, his desk held a LexisNexis terminal—an angular box with a built-in keyboard used for case law research; he used it as a surface for Post-it notes. He wrote documents longhand on a legal pad, handing them off to a typing pool staffed by, as Goldschmidt recalls, "aspiring actors."

Editing a document meant two associates sitting side by side with the new and old versions, reading the first word of every line aloud to mark where the draft had changed. He dashed to meet the mail courier at 9 p.m. to make sure clients had the documents in the morning. Goldschmidt saw this as valuable repetition, learning through what he calls "sweat equity."

He didn't study judgment; he accumulated it. Even as Microsoft Word replaced typing pools and due diligence moved online, much of the mental work of synthesizing information remained. Those reps became part of Goldschmidt's value to clients, said Jeffrey Horowitz, a longtime Bank of America executive who worked with him across multiple transactions.

"You're getting long-term advice—grounded in history and a real relationship," he said.

Regeneron remains a Skadden client, now a roughly $77 billion biotech. Its cofounder and CEO, Dr. Leonard Schleifer, remembers Goldschmidt as a "workhorse," citing his attention to detail and command of the law.

Now, with the legal industry on the cusp of another shift, artificial intelligence is beginning to absorb some of the routine work that once consumed junior lawyers' time. Goldman Sachs has said the technology could someday automate 44% of legal work. Goldschmidt's own introduction to the technology came from his son, then a Big Law associate, who gave him a demo of a legal software called Harvey.

The software could draft and find answers in documents that might take an associate hours of slogging. "It just blew me away," Goldschmidt said. That efficiency raised a fundamental question: How do you train young lawyers when machines do the work for them?

For Goldschmidt, the value of sweat equity isn't just hard work—it's the intellectual struggle of problem-solving. Learning, he said, happens when you "hit a brick wall and veer off" to find another path. If new tools surface answers instantly, he worries, junior lawyers may lose not only the habit of wrestling a question to its conclusion, but the legal fundamentals needed to recognize when a chatbot is hallucinating or getting it wrong.

Still, Goldschmidt is careful not to romanticize the past. "It may be easier," he said. But law, he argues, has never been a profession where fulfillment comes from sitting at a desk and simply executing tasks.

Inside Skadden, Goldschmidt said, there's a saying: Walk through walls for the client. That ethos only intensified as new tools arrived. Legal work, after all, is a service business. Email and cellphones reset expectations for speed and responsiveness. Now, clients are pushing law firms to adopt artificial intelligence in the name of more efficient service.

Skadden pays for its lawyers to have access to Harvey and other tools used for research, drafting, and document review. For Goldschmidt, even the early technology was a "double-edged sword." A BlackBerry meant he could finally go to a movie on a Saturday night without worrying he might miss a call. But it also meant there was no longer any real off-switch.

The culture didn't always allow lawyers to check out. Goldschmidt remembers around that time reading an article about email that described how Bill Gates would sit down at his computer at night and respond to his messages in one sitting. "How lucky is that guy," Goldschmidt remembers thinking, "that he can wait till the end of the day?"

As Goldschmidt prepared to retire on New Year's Eve, he remained optimistic about the next generation of lawyers, provided they remember that the job requires more than just prompting chatbots. Looking back on the shift from legal pads to large language models, he offers a final assessment of his four decades in the arena—not as a protagonist, but as an essential witness.

"I may not have invented anything. I may not have started a company that changed anything. But I had a front-row seat to all those people, those companies, who did."

David Goldschmidt's career spanned the transformation of legal practice from analog to digital, and now to algorithmic. His retirement marks the end of an era defined by sweat equity and intellectual struggle, even as the industry embraces tools that promise efficiency at the cost of depth.

The fundamental question he raises—how to train young lawyers when machines do the work for them—remains unanswered. Yet his optimism about the next generation suggests that the human elements of legal practice: relationship-building, judgment, and the willingness to "walk through walls for the client"—will endure.

For Goldschmidt, a fulfilling career has never been about sitting at a desk and simply executing tasks. It's about "stretching, meeting people, learning—seeing what's around the bend." As artificial intelligence reshapes the legal landscape, that wisdom may prove more valuable than any algorithm.