U.S. District Judge Jed Rakoff’s standoff with the U.S. Securities and Exchange Commission, Citigroup Inc. and the U.S. Court of Appeals for the Second Circuit officially ended on Tuesday, when the judge conceded that he must approve Citi’s $285 million settlement with the SEC over the bank’s role in marketing a doomed-to-fail investment.

Rakoff lost. But his initial refusal to sign off on the Citi deal sparked a nationwide conversation about Wall Street regulation and helped nudge the SEC to reassess its settlement strategies. And Rakoff didn’t give up without sending the message that his judicial superiors made a terrible error in forcing him to approve the settlement.