We can assert that the irony in Roosevelt's political legacy would have to lie opposite of elements in his youth. As a young person, Roosevelt did not exhibit the qualities of strength that were so much a part of his political legacy. As a child, Roosevelt suffered from asthma. It was a condition that was as much physical as it was emotional, something that the young Roosevelt encountered as a "nervous disease." Sudden and intense "mental emotions" were attributed to bringing on attacks on the young Roosevelt. As a child, Roosevelt's condition was precipitated by him feeling "doleful" and depressed. When he would experience scolding from his father, young Roosevelt would take a position of victimization:
"Don't scold me," he would say if he incurred his father's displeasure, "or I shall have the asthma." And so he would; his fears were as correct as they were convenient.
Roosevelt's condition as a child was one of "direst suffering." There was little hope in finding a cure and doctors were puzzled as to a diagnosis for alleviation of the youth's pain and his psychological sadness.
Another aspect of his youth that could be seen as ironic is that Roosevelt grew up in wealth and privilege. Roosevelt was not a rugged frontiersman as a young child. His entire surroundings consisted of medical attention of the highest possible caliber:
An attack comes at home and he is whisked into the night in a family carriage pulled by magnificent, matched horses, a carriage that may be summoned to the door at a moment's notice, whatever the hour. It is a very privileged kind of resolution to the crisis, not to mention an exciting one.
Even if the doctors failed to understand how to treat his asthma, there was no shortage of funds to try every possible avenue. Wealth is what helped to keep Roosevelt alive.
These aspects of Roosevelt's youth lie in opposition to the political legacy that Roosevelt established as President. The "cowboy persona" and the political legacy of facing down trusts with steely resolve in "expanding the power of the White House" lies in direct opposition to a child who was afflicted with physical ailments that could be enhanced with "mental emotions" and psychological episodes. His assertion of the "Square Deal" was made out of strength: "My action on labor should always be considered in connection with my action as regards capital, and both are reducible to my favorite formula – a square deal for every man." Roosevelt articulated a political position of strength, while as a youth, he would advocate positions of convenience due to his sickly condition.
Roosevelt's political legacy rests with "speak softly and carry a big stick." It was a legacy carved out of assertiveness and focus, elements needed to dissolve Standard Oil, become known as a "trustbuster," and deliver a 20,000 worded address to Congress imploring action to curb corrupt business practices. Yet, it also reflected a distinct attitude against the wealthy, the primary targets of Roosevelt's desire to increase federal oversight and regulation of businesses. The same wealth in which he lived his youth was the target of many of his initiatives. Wealthy individuals who believed they had "one of their own" in the White House found themselves in for a rather rude awakening. Roosevelt's political legacy of austerity and strength while seeking to reduce the power of the wealthy through increased government regulation are aspects that lie in opposition to his youth.