4. $97 Million On Linda's Two Failed Senate Bids - November 6 2012
When Linda McMahon conceded in her bid to become Connecticut US senator in 2012, she faced up to having nothing to show for $97 million of spending across her 2010 and 2012 campaigns. You could actually see a tearful and shell shocked looking Vince in the background of her concession speech. She had ran in both 2010 and 2012, with Vince throwing significant money and resources behind her. To spend nearly a hundred million across two campaigns, it was the most any candidate had ever spent out of their own pocket to try and win office. It failed. The McMahon family had funded it themselves, meaning a near hundred million hit to Vince's pride and bank account.
