Iron Man: Director of S.H.I.E.L.D. Annual #1 (2008)

Regime Change
Tony Stark recognizes Madame Hydra's rule of Madripoor as a global threat, but S.H.I.E.L.D. cannot intervene directly to depose her due to politics. As an alternative plan, he heads a team to bring about rebellion from within under the command of master criminal Tyger Tiger. It takes a lot of manipulation and planning, but he eventually succeeds in his goals.
Release Date: 2008