Count's Youngest Son is a Warlock - Chapter 25

Some say reincarnation is a blessing, but for me, it's a dreadful curse. Cursed with endless reincarnation, I've been reborn as a villain 137 times. And all 137 times, I've been toyed with and killed by heroes who are far more cruel than the said villains... If I can't win no matter what I do, then I'll crush those so-called heroes at their very roots. - Quality Fan Translations, Made by Fans for the Fans - Villain Takes Over The Academy

The era of the great pirates.

The sea is surging, the strong are destroying the sky and the earth, and they are fighting each other. It really makes people——

Can’t get up!

I, Rusilu Cullo, twenty-four years old, my biggest dream:

Live this life safely!

- Description from novelbuddy

In 2008 America, the advantages of being reborn were about to vanish, and Link could only rely on his powerful physique, attractive appearance, superior publicity tactics, and numerous scandals to gradually rise from obscurity to become a top influencer of the Times and a tycoon in the entertainment industry.

The most successful businessman of his time, who started from being a homeless orphan, died indignantly because of being plotted against by his most trusted aid, his own brother.