This article compares two legislative initiatives of President F.D. Roosevelt with the aim of finding an explanation for one of the failures of Roosevelt's presidency: his attempt to change the composition of the Supreme Court in 1937. Comparing Roosevelt's strategy and activities during the Court-packing crisis and drafting and processing the Lend-Lease act it can be concluded that the differences are not structural but gradual. In both cases he pushed the political system to the limits in about the same way, but in the Court-packing case this brinkmanship fails. Roosevelt misinterprets signals and misses good opportunities to come out of it a winner because of specific, and particular circumstances further explored in the article.