In this paper, we construct (many) Kolyvagin systems out of Stickelberger elements utilizing ideas borrowed from our previous work on Kolyvagin systems of Rubin-Stark elements. The applications of our approach are twofold. First, assuming Brumer’s conjecture, we prove results on the odd parts of the ideal class groups of CM fields which are abelian over a totally real field, and we deduce Iwasawa’s main conjecture for totally real fields (for totally odd characters). Although this portion of our results has already been established by Wiles unconditionally (and refined by Kurihara using an Euler system argument, when Wiles’s work is assumed), the approach here fits well in the general framework the author has developed elsewhere to understand Euler/Kolyvagin system machinery when the core Selmer rank is r > 1 (in the sense of Mazur and Rubin). As our second application, we establish a rather curious link between the Stickelberger elements and Rubin-Stark elements by using the main constructions of this article hand in hand with the “rigidity” of the collection of Kolyvagin systems proved by Mazur, Rubin, and the author.