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DiRegenati was born on October 21, 1850, in what was then Bavarian Venezia. His family was primarily Italian, with some scattered Bavarian heritage. His last name roughly translates to "from Regens". The Regens is an important river in Bavaria, and the namesake for the equally important city of Regensburg.
DiRegenati suffered many family tragedies during his early childhood. The death of his brother, Emanuel, proved a great stress for his father and mother, and the family's slip in poverty provided even more misery. However, dark clouds cleared by his teenage years as his parents relocated to Augsburg in search of better employment. DiRegenati's father became a Liberal parliamentarian in 1867, inspiring him to become politically active.
DiRegenati was not militarily active during the Bavarian Revolution, but did campaign for Liberal politicians and activists very frequently. After the worst of the revolution subsided in the 1880s, DiRegenati made his first mark in politics. He was elected to the Deutsch Diet in 1880, representing Venezia.
From 1880 to 1890, DiRegenati's fame and celebrity grew wildly, becoming known as a fiery Liberal who never backed down from a tense debate or issue. Years passed as he became a staple in Bavarian politics. Markus Helenkamp was so impressed with his performance and ability that he put DiRegenati on his 1890 Chancellery ticket for Vice-Chancellor.
Helenkamp was elected in 1890, brining DiRegenati with him.
As Vice-Chancellor of Bavaria, DiRegenati supported many liberal organizations, and co-sponsored many bills of his own.
The tragic assassination of Helenkamp in 1894 then thrust DiRegenati to the most powerful seat in Bavaria, that of the Chancellor.
As Chancellor, he hammered out the finer details of German unification, as well as pondering a campaign for a second term as Chancellor. When Germany unified, the seat of Bavarian chancellor was demoted to Governor-General, which DiRegenati effectively inherited. A failed Chancellery campaign in 1896 represented a dark time for DiRegenati, but he was luckily able to keep hold on his seat as Governor-General.
DiRegenati launched a second Chancellor campaign in 1900, this time defeating incumbent Friedrich von Gustrow, who he would later make Vice-Chancellor in 1902.
Since his inauguration 1901, DiRegenati has seen his share of success, and scandal. Most notably, the Hanoverian-Oldenburger Crisis caused many headaches for the German government after Hamburgian bills, aimed at rooting out Communists, ended up damaging Oldenburger relations with Beothuk natives.