Maybe this would be interesting:

A note to the librarian, 1925.

My advice (and request):

1) Classify the books not by author, but by the following themes:

    a) Philosophy;
    b) Psychology;
    c) Sociology;
    d) Political Economy;
    e) Finance;
    f) Industry;
    g) Agriculture;
    h) Co-operation;
    i) Russian history;
    j) History of other countries;
    k) Diplomacy;
    l) Foreign and internal trade;
    m) Military affairs;
    n) The national question;
    o) Congresses and conferences;
    p) The situation of the workers;
    q) The situation of the peasants;
    r) The Komsomol;
    s) The history of other revolutions in other countries;
    t) About the year 1905;
    u) About the February Revolution of 1917;
    v) About the October Revolution of 1917;
    w) About Lenin and Leninism;
    x) The history of the CPSU and the International;
    y) On the discussions in the CPSU (articles, brochures);
    y1 Unions;
    y2 Fiction;
    y3 Art criticism;
    y4 Political magazines;
    y5 Natural science magazines;
    y6 Various dictionaries;
    y7 Memoirs.

 

2) From this classification remove (and arrange separately): a) Lenin, b) Marx, c) Engels, d) Kautsky, etc.) Plekhanov, e) Trotsky g) Bukharin, h) Zinoviev and) Kamenev, k) Lafargue, l) Luxembourg, m) Radek.

3) All the others, classify by author, putting aside all sorts of books, small magazines, anti-religious wastepaper, etc. Stalin"

You could make some conclusions from point 2. But those could've changed with the years. Sadly, I didn't find any newer catalogs of Stalin's library.

Scan of the note, in Russian. (Автограф Сталина, РГАСПИ, ф. 558, оп. 1, д. 2510)

One historical figure that I know he admired is Ivan the Terrible (Ivan IV). He expanded Russian access to the Volga River and the trade that came with it, and greatly strengthened central authority. He then attempted to conquer Livonia, which led to a war resulting in much lost territory, wasted money, and weakening his empire.

He abdicated the throne for a short period of time, as a political maneuver. He some of the political class was unloyal, and knew he did not have a successor besides his son who he took with him, so he would be invited back. He came back on the term that he could handle those who he mistrusted as he pleased. This led to the creation of the Oprichniki, which was his personal guard. They were around a thousand strong, and terrorized those who Ivan mistrusted terribly. He did as he pleased with them, sending them wherever he felt there was dissent.

So it's pretty clear to see where Ivan IV inspired Stalin. I'm not sure of other historical figures he may have looked up to, though