Tony Accardo was an American criminal, who is considered to be one of the sharpest Chicago mob bosses of all time, with a career spanning over six decades. Starting out as a bodyguard for Al Capone, he slowly rose through the ranks, becoming the boss and finally the ultimate authority of the Outfit by the time he was 70. When he was in his 20s, he gained infamy for wielding the baseball bat as a weapon. However, in the later years, he much preferred to resolve conflicts without bloodshed. His intelligence, level-headedness and the habit of staying away from the spotlight not only helped him become more wealthy and powerful, but also allowed him to start new criminal avenues and acquire new territories to grow the Outfit’s businesses. Although Accardo was arrested multiple times during his tenure, he never had to spend time behind bars. He increased his personal wealth by investing in newspaper agencies, hotels, travel companies, trucking and car dealerships, commercial buildings, paper and lumber factories; and retail centers. He chose to stay away from media attention and was usually seen wearing a low-titled hat, covering his face. He enjoyed staying home with his family and entertaining his guests there.