Tsakos Energy Navigation (TNP) is a marine shipping company (mainly crude oil) that offers an array of high-yield equities including 5 series of preferred shares with dividend yields from 7.9% to 9.5% and common shares offering a 5.8% dividend yield. But before you start trying to decide which of Tsakos’ many high-yield securities you want to invest in, you might first want to consider whether you believe the business will actually produce the cash flows necessary to support those payments to investors. This article details the two biggest risks threatening Tsakos’ future ability to pay, and then reviews the differences between the company’s array of high yield securities. We conclude with our thoughts on how income-focused investors might want to “play” Tsakos.