Multinational Enterprises (MNEs) periodically decide on both which products to launch (or phase out) and in which global regions, thereby conducting an integrated products-countries consideration in diversification strategies. Over time, these diversification decisions can have a cumulative impact on the structure. Diversification literature has primarily focused on one of these two metrics rather than providing an integrated view; this work investigates both metrics. Considering deal-making as an execution instrument of strategies, a comparison of historic deals of MNEs with their current structure offers insights into the nature of the diversification strategies that were pursued. For the most active global deal-making pharmaceutical firms, we derive normalized deal diversity profile metrics in terms of their cumulative past product-countries’ preferences and compare them with the product-countries’ operations of their current subsidiaries. We rationalize MNE deal behaviors as means to shed, acquire and consolidate businesses to enable their market leadership aspirations. The analysis reveals two trajectories that have been actively favored in deals: one directed at niche products offered globally, and one directed at niche products in selected countries. The former is characterized by deals in a high number of countries, whereas the latter by two identifiably different product concentration levels. In contrast, trajectories directed at widely diverse products have been disfavored in deals. Understanding such directions and their pace can aid in global- or group-level strategy formulation, monitoring strategy execution, interpreting competitor moves and designing regional policies.