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Large corporations are unique, in that they (1) enter into adhesive contracts with millions of people, (2) get sued a lot, and (3) often use outside counsel.

What happens if a corporation—probably through outside counsel—argues an interpretation of the contract that helps them win one case but is otherwise a bad position for them? Is the corporation estopped from arguing the good position in the future?

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The doctrine of judicial estoppel could potentially be applied in the manner that you suggest.

The doctrine is applied in a manner that involves considerable discretion (unlike the similar doctrine of collateral estoppel, which makes judicial determinations against a party on the merits in a litigated case binding against the party against whom it was decided in future cases, in which there is much less judicial discretion). So, it isn't a lock solid winning argument that can be convincingly relied upon. But, it is a legitimate argument that a party can make in a lawsuit that would sometimes win.

Footnote

Large corporations are unique, in that they (1) enter into adhesive contracts with millions of people, (2) get sued a lot, and (3) often use outside counsel.

For what it is worth, most businesses and government agencies, large and small, enter into adhesive contracts, often with at least hundred or thousands of people, if not with millions of people, and many get into frequently lawsuits and sometimes use outside counsel. So, the uniqueness of large corporations is somewhat overstated in the question.

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