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 two-fold: 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 deduce Iwasawa's main conjecture for totally real fields (for totally odd characters). Although this portion of our results have already been established by Wiles unconditionally (and refined by Kurihara using an Euler system argument, when Wiles' 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. Assumption 1.1. θ χ K annihilates A χ K . We remark here that Wiles [Wil90a] proved that Brumer's conjecture as stated above follows from his proof [Wil90b] of the main conjecture of Iwasawa theory for totally real fields. In this paper, we prove the other way around, namely that, assuming Brumer's conjecture, one might also prove the main conjecture (see Theorem B below; see also Kurihara's work [Kur03] where he refines Wiles' result using a different type of Euler system argument).The first application of the treatment here is the following (Theorem 5.3 below):Theorem A. Suppose the hypothesis (A1) and Assumption 1.1 hold. Then,With a bit more work, we can prove the Iwasawa theoretic version of Theorem A, which we state below. Set Γ = Gal(k ∞ /k) and Λ = Z p [[Γ]], as usual. Let L ωχ −1 ∈ Λ denote the Deligne-Ribet p-adic L-function (see [DR80]). We recall in (5.2) the basic interpolation property which characterizes L ωχ −1 . Let Tw ρcyc be a certain twisting operator on Λ (see §5.2 below for its definition). For any abelian group A, let A ∨ := Hom(A, Q p /Z p ) denote its Pontryagin dual, and finally, let char(M) denote the characteristic ideal of a finitely generated Λ-module M (with the convention that char(M) = 0 unless M is Λ-torsion). Then we are able to prove (see Theorem 5.8 and Corollary 5.10 for a slightly improved version so as to include the case µ µ µ p ⊂ L):Theorem B. Suppose the hypotheses (A1)-(A2) as well as Assumption 1.1 hold. Assume also that L does not contain pth roots of unity. Then, Proposition 2.25. We have X (T, F can ) = r (= [k : Q]).Proof. This follows from [MR04, Theorem 5.2.15], applied with the base field k (instead of Q; we therefore have r real places instead of one) and using our assumption that χ is totally odd.Proposition 2.26. The core Selmer rank X (T, F L ) of the Selmer structure F L on T is one.