Robert “Bob” Allen

Company: AT&T (1986 - 1997)

Biggest asshole moment: Saying he felt "no pain" accepting more money and firing thousands of employees.

Allen coerced a merger between AT&T and computer company, NCR Corp., which became one of the worst business deals of all-time: costing the company $12 billion and resulting in 50,000+ layoffs in the long run. As AT&T struggled financially during the '90s, reports surfaced that the former CEO received stock options that increased his pay from $6.7 million to $16 million soon after he enforced terminations. Allen showed no remorse and shared his greedy views with company execs during an annual AT&T meeting in 1996: "I feel no pain in accepting the compensation that may eventuate if—and only if—the shareholders, the customers and the employees of AT&T also benefit.”