David Goldschmidt, who retired in January 2025 after 37 years at elite law firm Skadden, Arps, witnessed the legal industry’s complete transformation from analog to algorithmic—and he’s skeptical that AI will produce better lawyers. As global head of Skadden’s capital markets practice, Goldschmidt advised on over $300 billion in transactions in 2025 alone, including historic IPOs like Rivian Automotive’s $12 billion raise.
Goldschmidt’s career began in 1990 when he helped take Regeneron public, learning through what he calls “sweat equity”—the intellectual struggle of problem-solving that comes from wrestling with complex legal questions. He watched technology reshape legal work from typing pools and legal pads to Microsoft Word, online due diligence, and now artificial intelligence. His introduction to AI came through his son, a Big Law associate, who demonstrated Harvey, a legal AI software that can draft documents and find answers in minutes—work that once took associates hours.
While Goldschmidt acknowledges AI’s efficiency is impressive, he raises a fundamental concern about legal training: How do you develop judgment when machines do the foundational work? Goldman Sachs predicts AI could automate 44% of legal work, but Goldschmidt worries that instant answers from chatbots will prevent junior lawyers from developing the intellectual muscle memory needed to recognize when AI is hallucinating or producing incorrect results.
The 62-year-old partner is careful not to romanticize the past—he remembers the grueling hours of reading documents line-by-line and racing to meet mail couriers at 9 p.m. But he argues that learning happens when lawyers “hit a brick wall and veer off” to find another path. That struggle builds the fundamentals necessary for sound legal judgment.
Skadden, the fourth-highest-grossing law firm in the country, now provides its lawyers access to Harvey and other AI tools for research, drafting, and document review, responding to client pressure for more efficient service. Goldschmidt describes technology as a “double-edged sword”—BlackBerrys allowed him to attend movies without missing calls, but also eliminated any real off-switch from work demands.
Despite his concerns, Goldschmidt remains optimistic about the next generation, provided they remember that law requires more than prompting chatbots. His career advice emphasizes that fulfillment comes from “stretching, meeting people, learning—seeing what’s around the bend,” not just executing tasks at a desk.
Key Quotes
It just blew me away
Goldschmidt’s reaction when his son, a Big Law associate, demonstrated Harvey, an AI legal software that could draft documents and find answers in minutes—work that traditionally took associates hours of manual labor.
How do you train young lawyers when machines do the work for them?
Goldschmidt poses the fundamental question facing the legal profession as AI automates routine tasks that once provided essential training for junior associates, potentially undermining their development of legal judgment and fundamentals.
Learning happens when you hit a brick wall and veer off to find another path
Goldschmidt explains his concept of ‘sweat equity’—the intellectual struggle of problem-solving that builds legal expertise. He worries that AI-generated instant answers may prevent lawyers from developing the critical thinking needed to recognize when technology produces incorrect results.
A fulfilling career is going out there, stretching, meeting people, learning—seeing what’s around the bend
Goldschmidt’s advice to the next generation emphasizes that law has never been about simply executing tasks at a desk, but requires active engagement and relationship-building that AI cannot replicate.
Our Take
Goldschmidt’s retirement marks a generational handoff at a critical juncture for professional services. His skepticism about AI isn’t Luddite resistance—it’s informed concern from someone who successfully adapted through multiple technological revolutions. The distinction he draws between efficiency and expertise development is crucial: AI may produce documents faster, but can it produce better lawyers?
The legal industry’s AI adoption reveals a principal-agent problem: clients want lower costs through automation, but they ultimately need lawyers with judgment honed through experience. Firms like Skadden face pressure to deploy AI while maintaining the apprenticeship model that produces rainmakers like Goldschmidt. His warning about AI hallucinations underscores that junior lawyers need foundational knowledge to quality-check AI output—creating a paradox where they need expertise to supervise tools that prevent them from gaining that expertise. This “automation paradox” will define professional training across industries as AI capabilities expand.
Why This Matters
This story captures a pivotal moment in the legal profession’s AI transformation through the eyes of a veteran who witnessed four decades of technological change. Goldschmidt’s concerns about AI undermining junior lawyer development highlight a challenge facing every knowledge-based profession: how to maintain expertise and judgment when automation handles foundational tasks.
With Goldman Sachs predicting 44% of legal work could be automated, law firms face pressure to adopt AI for efficiency while preserving the training pipeline that produces experienced partners. This tension between client demands for cost-effective service and the need for deep professional development will shape how elite firms like Skadden structure careers.
The broader implications extend beyond law—any field requiring accumulated judgment faces similar questions about AI’s impact on expertise development. Goldschmidt’s “sweat equity” concept suggests that struggle and repetition aren’t just hazing rituals but essential learning mechanisms. As AI tools like Harvey become standard in professional services, industries must grapple with whether efficiency gains come at the cost of developing the next generation’s critical thinking abilities.
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Source: https://www.businessinsider.com/skadden-david-goldschmidt-retires-career-advice-ai-2026-1