Bankruptcy Shield as a Sword: The Startup Gets Acquired Without Being Acquired

The proposed sale of Spirit Airlines’ enormous internal dataset to Google exposes a potentially dangerous new loophole in the AI economy. Google won a bankruptcy auction with a $10 million bid for Spirit’s enterprise data and says the material could help improve its products and AI models. The corpus reportedly includes approximately 100 million emails, 500 million Microsoft Teams messages, software code, operational information and decades of business records. (Reuters)

But there is a threshold question that shouldn’t get lost in the excitement over turning bankrupt companies into AI training datasets: Did Spirit actually own everything it proposed to sell?

Possession Is Not Ownership

Springshot, a technology startup whose proprietary airline-operations platform was embedded in Spirit’s technology stack for its final three years, says potentially not. Springshot has objected that the sale agreement defines the dataset so broadly that it may encompass Springshot’s own intellectual property and proprietary information. It wants the bankruptcy court to require a forensic process separating Spirit’s property from property belonging to third parties before anything goes to Google. (Ars Technica)

Springshot founder Doug Kreuzkamp states the basic principle perfectly: “The possession of IP is not ownership.” After all, a debtor’s server is a container, not a chain of title. It may hold the debtor’s property alongside licensed technology, vendor trade secrets, confidential communications, employee information and intellectual property belonging to somebody else. Bankruptcy shouldn’t improve the debtor’s title.

Bankruptcy as a Sword

That becomes particularly important with AI because bankruptcy can potentially be transformed from a shield for a distressed debtor into a sword for the purchaser. The sequence is straightforward: Startup develops technology → licenses it to customer → technology and know-how become embedded in customer’s systems → customer fails → bankruptcy estate sells its “dataset” → AI company trains on the corpus.

The bankruptcy proceeding has now done something much more consequential than liquidating the debtor’s assets. It may have created an efficient mechanism for aggregating information and transferring it to an AI company for a new use. That’s the loophole.

The Startup Gets Acquired Without Being Acquired

And that’s where this becomes an antitrust problem. Springshot has spent roughly 15 years developing technology used to improve airline operations. Ars reports that Google recently announced a five-year partnership with Ryanair involving airline operational data and Gemini Enterprise—putting Google’s AI efforts in an area where Springshot itself operates. Springshot consequently fears that its proprietary information could end up helping a vastly larger company compete with it.

Think about the alternatives. Google could develop competing technology. It could license Springshot’s technology. It could partner with Springshot. It could potentially acquire Springshot.

Or, potentially: Buy the data estate of Springshot’s bankrupt customer in a bankruptcy auction. That last possibility is profoundly different. Google doesn’t acquire the startup. It potentially acquires what the startup knows. There is no acquisition price paid to the startup. No negotiated license. And no conventional acquisition of the competitor to scrutinize.

As Springshot warns, the precedent could allow large amounts of startup IP to migrate to enormously powerful companies through bankruptcy proceedings. In other words, the startup gets acquired without being acquired. And there may be nothing they can do about it.

A Competition Loophole

That makes the bankruptcy loophole a competition loophole. Startups necessarily expose substantial information to enterprise customers. Integration requires documentation, workflows, support communications, operational data and technical knowledge.

Normally contracts, confidentiality obligations, trade-secret law and property rights establish boundaries around that information. But if those boundaries become uncertain when the customer goes bankrupt, the economics of dealing with large enterprise customers change.

A startup could survive while its customer fails—only to discover that the customer’s bankruptcy estate proposes to sell information embodying the startup’s technology to a company with virtually unlimited resources. The customer went bankrupt, so why should the startup’s competitive advantage be liquidated with it?

Procedure Becomes the Product

There is a broader procedural inversion here. Large corporate defendants have long understood that legal procedures nominally directed against them can sometimes produce valuable affirmative rights. A class action, for example, is ostensibly a device for aggregating claims against a defendant. But settlement can also aggregate something enormously valuable for the defendant: releases and finality.

The procedure itself creates economic value. AI may give bankruptcy proceedings a similar secondary function. Bankruptcy ostensibly protects the debtor and organizes an orderly disposition of its property. Or that’s the party line. But to an AI company seeking enormous quantities of authentic enterprise data, bankruptcy can provide something else: Aggregation.

Instead of negotiating separately with every employee, contractor, vendor and technology supplier whose information resides in a company’s systems, the purchaser buys one enormous “dataset” from the estate. What began as the debtor’s shield risks becoming the purchaser’s sword.

De-Identification Doesn’t Fix Title

Google says it will not receive personal information, and Spirit’s dataset is supposed to undergo de-identification. That’s important for privacy, but it doesn’t resolve ownership. Anonymization is not assignment. Removing a person’s name doesn’t transfer a vendor’s trade secrets. And de-identifying employee communications doesn’t necessarily establish that they can be repurposed for AI training. Privacy, ownership, confidentiality and authorization are separate questions.

A Caution for Startups: Treat Customer Data Like Inventory in a Warehouse

There is a useful analogy here to secured lending. A bank lending against inventory does not assume that everything physically sitting in the borrower’s warehouse belongs to the borrower. It identifies the collateral, determines what rights the borrower actually has in it, perfects its security interest, and worries about priority, proceeds, commingling and property belonging to third parties. So the Spirit case highlight the need to think about creditworthiness as a material deal point.

AI startups may want to start thinking about their data in much the same way. A customer’s servers are increasingly the digital equivalent of the warehouse. They may contain customer-owned information alongside licensed technology, vendor trade secrets, proprietary workflows, confidential communications, derived data and other material the customer merely possesses. If the customer enters bankruptcy, the danger is that all of this gets swept into a broadly defined “enterprise dataset” and auctioned as though possession established ownership. It doesn’t.

That means startups should protect themselves before a customer’s financial distress ever arises. Contracts should clearly establish ownership, permitted uses, AI-training restrictions, return and deletion obligations, and what happens upon insolvency. Proprietary information should be identifiable and segregated where practicable, with sufficient provenance to establish what belongs to whom.

There may even be circumstances where traditional secured-credit techniques deserve consideration as additional protection. But the distinction is important: Ownership is the first line of defense: “That isn’t property of the bankruptcy estate.” A security interest is the second: “If it is property of the estate, our rights have priority.”

A startup generally wants to win the first argument. Carelessly taking a security interest in property the startup claims to own could muddy that position rather than strengthen it, so Article 9 protection requires careful drafting.

The larger caution is simple: Bankruptcy courts have spent generations distinguishing what is in a debtor’s warehouse from what the debtor actually owns. AI should not erase that distinction merely by replacing the warehouse with a server. For startups whose technology becomes embedded in customers’ systems, data-title planning may now need to become as routine as IP assignments, confidentiality provisions and cybersecurity. The time to establish ownership and provenance is before the customer’s servers—and everything sitting inside them—show up in a bankruptcy auction.

The Rule Should Be Simple

AI has transformed old corporate records from storage liabilities into valuable assets. Spirit’s data sale shows just how valuable: companies are bidding millions for records of how real humans communicate, solve problems and operate businesses. That makes it essential to get the rule right now. Before a bankruptcy court asks what is this dataset worth?, it should ask: What exactly did the debtor own?

Bankruptcy can transfer the debtor’s assets. It should not manufacture AI rights the debtor never possessed. And it certainly shouldn’t become a mechanism through which a dominant AI company can acquire the accumulated knowledge of a startup without ever acquiring the startup itself.

Ars Technica’s report on the Spirit/Springshot dispute

Google’s “AI Overviews” Draws a Formal Complaint in Germany under the EU Digital Services Act

A coalition of NGOs, media associations, and publishers in Germany has filed a formal Digital Services Act (DSA) complaint against Google’s AI Overviews, arguing the feature diverts traffic and revenue from independent media, increases misinformation risks via opaque systems, and threatens media plurality. Under the DSA, violations can carry fines up to 6% of global revenue—a potentially multibillion-dollar exposure.

The complaint claims that AI Overviews answer users’ queries inside Google, short-circuiting click-throughs to the original sources and starving publishers of ad and subscription revenues. Because users can’t see how answers are generated or verified, the coalition warns of heightened misinformation risk and erosion of democratic discourse.

Why the Digital Services Act Matters

As I understand the DSA, the news publishers can either (1) lodge a complaint with their national Digital Services Coordinator alleging a platform’s DSA breach (triggers regulatory scrutiny);  (2) Use the platform dispute tools: first the internal complaint-handling system, then certified out-of-court dispute settlement for moderation/search-display disputes—often faster practical relief; (3) Sue for damages in national courts for losses caused by a provider’s DSA infringement (Art. 54); or (4) Act collectively by mandating a qualified entity or through the EU Representative Actions Directive to seek injunctions/redress (kind of like class actions in the US but more limited in scope). 

Under the DSA, Very Large Online Platforms (VLOPs) and Very Large Online Search Engines (VLOSEs) are services with more than 45 million EU users (approximately 10% of the population). Once formally designated by the European Commission, they face stricter obligations than smaller platforms: conducting annual systemic risk assessments, implementing mitigation measures, submitting to independent audits, providing data access to researchers, and ensuring transparency in recommender systems and advertising. Enforcement is centralized at the Commission, with penalties up to 6% of global revenue. This matters because VLOPs like Google, Meta, and TikTok must alter core design choices that directly affect media visibility and revenue.In parallel, the European Commission/DSCs retain powerful public-enforcement tools against Very Large Online Platforms. 

As a designated Very Large Online Platform, Google faces strict duties to mitigate systemic risks, provide algorithmic transparency, and avoid conduct that undermines media pluralism. The complaint contends AI Overviews violate these requirements by replacing outbound links with Google’s own synthesized answers.

The U.S. Angle: Penske lawsuit

A Major Publisher Has Sued Google in Federal Court Over AI Overview

On Sept. 14, 2025, Penske Media (Rolling Stone, Billboard, Variety) sued Google in D.C. federal court, alleging AI Overviews repurpose its journalism, depress clicks, and damage revenue—marking the first lawsuit by a major U.S. publisher aimed squarely at AI Overviews. The claims include an allegation on training-use claiming that Google enriched itself by using PMC’s works to train and ground models powering Gemini/AI Overviews, seeking restitution and disgorgement. Penske also argues that Google abuses its search monopoly to coerce publishers: indexing is effectively tied to letting Google (a) republish/summarize their material in AI Overviews, Featured Snippets, and AI Mode, and (b) use their works to train Google’s LLMs—reducing click-through and revenues while letting Google expand its monopoly into online publishing. 

Trade Groups Urged FTC/DOJ Action

The News/Media Alliance had previously asked the FTC and DOJ to investigate AI Overviews for diverting traffic and ‘misappropriating’ publishers’ investments, calling for enforcement under FTC Act §5 and Sherman Act §2.

Data Showing Traffic Harm

Industry analyses indicate material referral declines tied to AI Overviews. Digital Content Next reports Google Search referrals down 1%–25% for most member publishers over recent weeks; Digiday pegs impacts as much as 25%. The trend feeds a broader ‘Google Zero’ concern—zero-click results displacing publisher visits.

Why Europe vs. U.S. Paths Differ

The EU/DSA offers a procedural path to assess systemic risk and platform design choices like AI Overviews and levy platform-wide remedies and fines. In the U.S., the fight currently runs through private litigation (Penske) and competition/consumer-protection advocacy at FTC/DOJ, where enforcement tools differ and take longer to mobilize.

RAG vs. Training Data Issues

AI Overviews are best understood as a Retrieval-Augmented Generation (RAG) issue. Readers will recall that RAG is probably the most direct example of verbatim copying in AI outputs. The harms arise because Google as middleman retrieves live publisher content and synthesizes it into an answer inside the Search Engine Results Page (SERP), reducing traffic to the sources. This is distinct from the training-data lawsuits (Kadrey, Bartz) that allege unlawful ingestion of works during model pretraining.

Kadrey: Indirect Market Harm

A RAG case like Penske’s could also be characterized as indirect market harm. Judge Chhabria’s ruling in Kadrey under U.S. law highlights that market harm isn’t limited to direct substitution for fair use purposes. Factor 4 in fair use analysis includes foreclosure of licensing and derivative markets. For AI/search, that means reduced referrals depress ad and subscription revenue, while widespread zero-click synthesis may foreclose an emerging licensing market for summaries and excerpts. Evidence of harm includes before/after referral data, revenue deltas, and qualitative harms like brand erasure and loss of attribution. Remedies could include more prominent linking, revenue-sharing, compliance with robots/opt-outs, and provenance disclosures.

I like them RAG cases.

The Essential Issue is Similar in EU and US

Whether in Brussels or Washington, the core dispute is very similar: Who captures the value of journalism in an AI-mediated search world? Germany’s DSA complaint and Penske’s U.S. lawsuit frame twin fronts of a larger conflict—one about control of distribution, payment for content, and the future of a pluralistic press. Not to mention the usual free-riding and competition issues swirling around Google as it extracts rents by inserting itself into places it’s not wanted.

How an AI Moratorium Would Preclude Penske’s Lawsuit

Many “AI moratorium” proposals function as broad safe harbors with preemption. A moratorium to benefit AI and pick national champions was the subject of an IP Subcommittee hearing on September 18. If Congress enacted a moratorium that (1) expressly immunizes core AI practices (training, grounding, and SERP-level summaries), (2) preempts overlapping state claims, and (3) channels disputes into agency processes with exclusive public enforcement, it would effectively close the courthouse door to private suits like Penske and make the US more like Europe without the enforcement apparatus. Here’s how:

Express immunity for covered conduct. If the statute declares that using publicly available content for training and for retrieval-augmented summaries in search is lawful during the moratorium, Penske’s core theory (RAG substitution plus training use) loses its predicate.
No private right of action / exclusive public enforcement. Limiting enforcement to the FTC/DOJ (or a designated tech regulator) would bar private plaintiffs from seeking damages or injunctions over covered AI conduct.
Antitrust carve-out or agency preclearance. Congress could provide that covered AI practices (AI Overviews, featured snippets powered by generative models, training/grounding on public web content) cannot form the basis for Sherman/Clayton liability during the moratorium, or must first be reviewed by the agency—undercutting Penske’s §1/§2 counts.
Primary-jurisdiction plus statutory stay. Requiring first resort to the agency with a mandatory stay of court actions would pause (or dismiss) Penske until the regulator acts.
Preemption of state-law theories. A preemption clause would sweep in state unjust-enrichment and consumer-protection claims that parallel the covered AI practices.
Limits on injunctive relief. Barring courts from enjoining covered AI features (e.g., SERP-level summaries) and reserving design changes to the agency would eliminate the centerpiece remedy Penske seeks.
Potential retroactive shield. If drafted to apply to past conduct, a moratorium could moot pending suits by deeming prior training/RAG uses compliant for the moratorium period.

A moratorium with safe harbors, preemption, and agency-first review would either stay, gut, or bar Penske’s antitrust and unjust-enrichment claims—reframing the dispute as a regulatory matter rather than a private lawsuit. Want to bet that White House AI Viceroy David Sacks will be sitting in judgement?