Dhameystir weedha soo socota: Ka dib markii uu shahaadada Bachelor of Arts ka qaatay, Donovan wuxuu labo sano ku qaatay Columbia Law School, halkaas oo uu ku ahaa arday ay isku fasal ahaayeen Franklin D. Roosevelt, wuxuuna wax ka bartay Harlan Fiske Stone. Markii uu ku soo laabtay Buffalo, wuxuu ku biiray shirkadda sharciga ee la ixtiraamo ee Love &amp; Keating sanadkii 1909 iyo, laba sano ka dib, wuxuu furay shirkaddiisa Buffalo isaga oo kaashanaya arday uu dhigan jiray Columbia, Bradley Goodyear. Sanadkii 1914, shirkadoodii waxay la midoobeen mid kale, waxayna noqdeen Goodyear & O'Brien. Sanadkii 1912, Donovan wuxuu gacan ka geystay sameynta, wuxuuna noqday hogaamiyaha, ciidanka fardooleyda ee New York National Guard. Ciidankaan waxaa lasoo xirey 1916 waxana ay ka howlgaleen xadka maraykanka iyo meksiiko intii lagu guda jiray howlgalkii dowlada maraykanka ee ka dhanka ahaa
Pancho Villa. waa wax aad u xiiso badan. Wuxuu bartay istaraatiijiyada militariga iyo xeeladaha dagaalka. Wuxuu sidoo kale koorsooyin u qaatay New York City oo uu ka qaatay xiddig masraxa ah, Eleanor Robson. Sanadkii 1914, wuxuu guursaday Ruth Rumsey, oo ah dhaxal sugaha Buffalo oo dhigatay Rosemary Hall.