In a world with differing opinions regarding capital investments, it is necessary to understand the expected returns for each investment option an investor may exercise. All investors seek maximum returns on their investments, and here the study evaluates the projected incomes of initial investments when exposed to two different strategies. Approximately $36,000 was invested into each, a portfolio of stocks entered into a Dividend Reinvestment Plan, and a portfolio of stocks exposed to a new strategy. This new strategy was a risk averse alternative to the DRIP and its portfolio market value was compared to that of the DRIP portfolio for eleven years. The immediate purposes of this study are 1) to measure the effect that dividend reinvestment has on a high dividend yielding portfolio, and 2) analyze the implications of using these dividend payments as capital for treasury bill investments. The findings of this thesis can be used by investment managers to implement new strategies that go beyond the realm of typical investment approaches