The Maronite–Syria relationship is troublesome, and one can say that the two sides are diametrical opposites. The Maronites, in general, represent the aspiration for an independent Lebanon, while Syria considers Lebanon a part of “Greater Syria” and aspires to annex the Lebanese territories. The Maronite community has consistently resisted these aspirations. However, the Maronite community is not a coherent one, which is reflected in its approach toward Syria. In fact, the Maronite leadership has adopted three different approaches toward Syria: an integrative one that aspires to full cooperation with Syria; a separatist one that strongly considers Lebanon and Syria to be separate states; and a pragmatist one that adheres to intimate or unfriendly ties according to local Lebanese interests. This article introduces the three Maronite approaches and claims that one cannot disassociate these approaches, especially the pragmatist one, from the Syrian policy toward Lebanon, which includes changing alliances according to Syria’s political interests. Moreover, the article suggests that these approaches will remain in place regardless of which Maronite leader supports each one and regardless of who will rule in Syria.