Why does the poet keep saying "He had his dream?

To emphasize a theme.

Explanation:

In the given poem, the poet Paul Laurence Dunbar keeps pronouncing that 'he had his dream' in order to outline the central idea of the poem which is to motivate the readers to stay hopeful and positive. The poet wishes to convey that irrespective of the 'toil and strife,' 'stormy-dark-clouds,' 'failures,' and 'raging tempests,' keep your optimistic 'hue' alive and better things will be your way. Thus, he says regardless of the obstacles and struggles keep your dream and spirit alive.

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