The paper grows out of two observed trends in corporation bankruptcy practice: first, reorganizations are increasingly structured by deals agreed to by insiders (including controlling creditors) before cases are filed, and bankruptcy courts have shown a willingness to adopt these deals within the chapter 11 process, despite concerns that the deals might not strictly comply with the Bankruptcy Code. But at the same time, there is a growing backlash – seen not only in academic writing, but also in appellate court decisions – against the flexible, deal culture that the bankruptcy courts have embraced. My paper shows that these opposing forces are not new. By looking at the long history of corporate bankruptcy – going back to the initial railroad insolvencies before the Civil War – I show how the story of American corporate reorganization law exhibits a distinctive pattern: a long, slow wave, drifting between flexibility and fairness. I argue that movements toward the extreme “fairness” pole are inherently unstable. In particular, because moves to extreme fairness tend to render reorganization systems unusable, the need for a functional reorganization system will inherently force a move back from fairness and toward flexibility. I conclude by arguing that changes to help the legitimate interests of small players getting crushed in the current system are worthwhile, but “reforms” that ultimately help distressed debt investors or other asset managers extract greater returns from bankrupt corporations are misguided at best. Moreover, as shown by an analysis of the prior reign of tremendous fairness – from about 1938 to 1978 – such a system is inherently unstable because the corporate reorganization system becomes unworkable. Rigidity increases the pressure for change. The best solution then is to scale back the extremes of the present ultra-flexible chapter system, without going so far as to thwart its very utility.