Chegg — once a poster child for pandemic-era edtech growth — is now in free fall. In 2025 the company announced it would slash 45 % of its workforce, citing plunging web traffic, collapsing revenue, and the onslaught of AI tools that let students bypass paid homework help altogether.
It’s a dramatic reversal for a company that sold itself as a learning aid. But behind that collapse lies an even more troubling paradox: many teacher pension funds and public retirement systems — in whose names educators put decades of trust — hold millions in Chegg stock. Why would those funds invest in a company whose business model many of their own beneficiaries see as unethical, even corrosive?
We’ve seen this pattern before. In the early 2000s, retirement funds like these were major institutional investors in for-profit higher education companies such as EDMC, ITT Tech, and the University of Phoenix. Those institutions promised strong returns but ultimately collapsed under fraud allegations, predatory practices, and declining enrollments. Many public-sector workers indirectly suffered as the funds lost money. Chegg’s story looks eerily similar: high growth promises, an ethically contested business model, and exposure of public retirement funds to extreme financial risk. The repetition suggests a structural pattern: when education is financialized and commodified, the people meant to serve it — educators and students — are exposed to both moral and economic hazards.
The Downward Spiral: Why Chegg Is Crashing
Chegg’s decline didn’t begin yesterday. It was seeded by technological disruption and a fragile business model dependent on volume, content access, and student compliance. Generative AI tools such as ChatGPT and Bard have undercut Chegg’s core service: paid homework help and explanations. Students can often get free answers faster and more flexibly. Google’s “AI overviews,” which display answer snippets directly in search results, divert traffic away from Chegg’s site, reducing ad and subscription conversions. Chegg has even sued Google, alleging unfair competition.
Earlier in 2025, Chegg laid off 22 % of its staff and closed its U.S. and Canada offices to cut costs. That was supposed to be a stabilization move, but it foreshadowed deeper troubles. The more recent 45 % layoff is sweeping: 388 jobs are being cut, $15–19 million in severance charges are expected, and $100–110 million in cost savings are projected for 2026. Chegg’s stock has lost approximately 99 % of its value since its 2021 peak. Yet the company is still pursuing a pivot toward B2B “skilling” markets, though skeptics doubt whether this can make up for the erosion of its original model. In short, Chegg is facing structural obsolescence. The ecosystem that once made its growth plausible is collapsing around it.
Pension Funds and the Strange Attraction to Chegg
Several public pension and teachers’ retirement systems hold millions in Chegg: Kentucky Teachers’ Retirement System owns $4.5 million, California State Teachers’ Retirement System owns $4 million, New York State Common Retirement Fund owns $13 million, Colorado Public Employees’ Retirement Fund owns $9.3 million, California Public Employees’ Retirement Fund owns $5.3 million, a Florida retirement fund owns $3.3 million, Ohio Public Employees Retirement owns $1.5 million, and the Teacher Retirement System of Texas owns $630,000.
These investments raise hard questions. Do pension fund managers assume Chegg will survive its technological disruption? Are they prioritizing short-term returns over long-term reputational or ethical risk? Do they believe the stock is undervalued and thus a “contrarian bet”? Are they following passive index allocations rather than making deliberate choices? Some fund managers defend such investments as fulfilling fiduciary duty: to maximize returns for their beneficiaries within acceptable risk parameters. Ethical considerations, they argue, should not trump financial sustainability — especially in a system underfunded and under stress. But when the bet fails, the consequences fall hardest on retirees, educators, and the public who trusted those funds to safeguard their futures.
Do We Owe Them Sympathy?
It’s tempting to feel a bit sorry: pension funds losing money is a headline nobody wants. But sympathy is complicated. These funds store and grow the life savings of public-sector workers — teachers, librarians, and staff. A poorly timed speculative investment can damage retiree security and erode public trust. On the other hand, this is no innocent failure; it is a foreseeable risk in backing a business facing existential challenges. It reflects a broader pattern of financialization in education: turning learning into a profit-seeking venture, exposing it to wild swings, and treating educators and students as market participants. Losses are regrettable, especially at the human level, but they also demand accountability. Institutions must explain why they placed trust in Chegg when its vulnerabilities were visible.
What This Reveals: Institutional Contradiction
This episode exposes several deeper contradictions at the intersection of education, finance, and values. Many educators see Chegg as a threat to academic integrity, yet the institutions managing their retirement funds believed in its upside. Some investors are attracted to the “turnaround bet,” seeing potential in a company trading at a fraction of its former value, though the risk is very high. Some funds may hold Chegg because their portfolios track broad indices, ceding moral discretion to the market. Education has become infrastructure built on venture logic, and the Chegg collapse is a warning: when learning becomes a commodity, its institutions become as unstable as any tech startup. Finally, if pension funds backed a cheating-enabled platform, what else might their capital support, and how does that affect trust in those institutions?
A Moral and Institutional Reckoning
Chegg’s collapse is not just a market drama; it’s a moral and institutional reckoning. A company built on a questionable model is now evaporating under AI pressure. Meanwhile, public pension funds — meant to safeguard the futures of educators — placed bets on that very evaporation.
We might feel a pang of sympathy for the financial losses. But our greater duty is to probe the judgment of those entrusted with public capital, and to demand coherence between values and investment. If the administrators of teacher retirement funds cannot align ethics with asset allocation, then their claims to serving the public good are weakened — and so is the trust on which the idea of public education depends.
Sources
Barron’s: “Chegg Is Suing Google. The Stock Is Sinking.”
Reuters: “Chegg to lay off 22% of workforce as AI tools shake up edtech industry.”
SF Chronicle: “Bay Area educational tech company slashes 248 jobs as students turn to AI tools for learning.”
The Cheatsheet Substack: “Meet Chegg’s Biggest Backers.”
The Chronicle of Higher Education: “Work in Public Education and Hate Chegg? You Might Be an Investor.”
Wikipedia: “Chegg”
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