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By 1959, George H. W. Bush’s Zapata Oil Company was booming. With its success, the Bush family (who had also known hard times), left Texas for New York. Where this move was a perfect fit for Father George, it was jarring for George Junior who had spent his whole life in Midland.

On the cusp of adolescence, the change brought new unwanted pressures on George, in particular his enrollment in an upscale elite private school where he struggled with the curriculum. But, that was only the beginning. Later when he was sent to Phillips Academy in Andover, Massachusetts, the culture shock was even more pronounced. It was clear that he was meant to follow in the footsteps of his father, but it was a rough road for George who didn’t fit into those very big footsteps.

Now separated from his old buddies, the new school felt like a foreign culture where he was hobnobbing with the sons of America’s wealthiest families. In desperation, George turned to what he knew best—humor–to get himself noticed. His witty, jocular personality soon won him a circle of admirers.

It was also at Andover that George began to use a device that served him well throughout his life, including his surprising rise to the presidency. He began to lower expectations for himself. Then in a turnabout, he would abruptly switch course and perform better than was expected. Additionally he learned to divert attention from his own shortcomings. It didn’t take long for Junior to become an expert at wielding these principles with a skill and subtlety that even his talented father could not match.

Back when he was a kid in Midland, George, Jr. lived and breathed baseball. There, however, he quickly discovered he would never be the star that both his grandfather and father had been at Yale. So, in order to compete, he worked at developing an acid witticism which he combined with a contagious personality. Both worked at winning over the student bodies at Andover and then Yale. It seemed that everyone he met became his friend and wanted to join in on his irreverent high jinks.

In no time he became as popular as the schools’ most gifted athletes. Unexpectedly, he also had his moments of baseball glory where he so convincingly downplayed his abilities that when he did play a good game, his success was magnified.

The summer before going to Yale, George pretended he had no desire to follow in his father’s footsteps. “I really don’t want to go to Yale,” he told brother Jeb, “I just applied to please dad.” When his acceptance letter arrived, however, he didn’t waste a minute packing his bags. There he was tapped to join the exclusive Skull and Bones. Membership meant nothing to him other than representing another notch in his gun; one more thing his father had done.

More than anything, he resented the privileged world into which he had been thrust. So rather than target his father (something he could never do), he often needled surrogates. He saw Nicholas Brady, the illustrious Skull and Bones figure who later served as Secretary of the Treasury in his father’s cabinet, as a pompous snob. Brady equally disliked the young Bush for not showing him due deference.

Years before, Father George had delayed entering Yale so that he could fly torpedo bombers in W.W.II. Junior was equally tempted by the war in Vietnam. From his first day at Yale, he talked about his desire to be a pilot. So, upon graduation he joined the Texas Air National Guard. It seems it was not about Vietnam or patriotism or giving back or the Bush family ethic. It was all about competing with Dad. But, alas, Junior’s time at Yale had been so uneventful, that his father did not even attend his graduation.

Nevertheless, within a year, George was soaring through the clouds in an F-102 Delta Dagger. By the fall of 1973, this ended when he received an honorable discharge from the national guard. It left him, albeit, baffled as to what to do next. George drifted here and there ever mindful of his father’s political roller coaster ride which had been sometimes hurtful and disappointing while at other times victorious and incredible. Additionally, Junior’s drinking, which had begun at Yale, was by now out of control. Later his volunteer stints at campaigning were often descents into alcohol and promiscuous debauchery. He described his life at that time as “non-stop booze and sex.” Shiftless and clueless as to how to accomplish the most difficult part of his climb upward, he was at a loss as to where to begin the millionaire part: the role of businessman. The higher he climbed, the more elusive it became. Whereas the oft repeated sagas of the Bush men—who by themselves had accomplished spectacular things—made impressive tales for little boys, it drove a grown man to drink.

Admittedly, Junior gave the distinct sense that the Bush men were a declining lot. And they actually were … in size! Grandfather Prescott had stood an impressive six feet, four inches tall, while George Senior was slightly less notable at six feet two. Star-crossed George Junior was not even six feet.

Furthermore, they even descended in importance during their times at Yale. Grandfather had been a baseball hero, Father George a national collegiate All-Star, and George Junior was, well, a cheerleader.

Additionally, Grandfather had fought in the terrible Meuse-Argonne offensive in W.W.I, Father George had been a certified war hero in W.W.II with a chest full of medals, whereas George Junior had not seen a minute of action in the Vietnam War. Each, it seemed, was a declining version of their former selves.

Moreover, in the world of commerce, Grandfather had become a millionaire extraordinaire at Brown Brothers Harriman before his illustrious career in the U.S. Senate. Father George had advanced from being a broom pusher at Dresser Industries to founding his own highly successful oil company—even though his accomplishment was anemic compared to his father’s. Twice George Senior attempted to win a seat in the U.S. Senate and failed, finally winning the lesser job of congressman, an unimportant position which was decried by his own dad. Thus with the Senate out of reach, Father George accepted the position of U.N. ambassador. It was considered a consolation prize.

If each generation was a downsized version of the one before it, George, Jr., by comparison, had no prospects at all. Twenty-six years old, with little interest in either work or marriage—and with the spotlight now being on his more serious brother, Jeb—no one in the family had any expectations of Junior entering into the public service game.

In 1975, after a nearly thirty-year absence, Junior returned to Texas. His plan was to make millions in the oil industry even though he arrived broke, with only $15,000 in start-up funds left over from his share of the family education trust. Still he yearned to become financially independent and perhaps even fast track himself into public service. At least that was his plan.

(to be continued)