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Jim Sheppard of South Portland is shown in a photo from 1944, when he was serving as a staff sergeant in Italy.

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Jim Sheppard of South Portland at one point worked as a mechanic on P-51 Mustangs, like the model plane he’s holding. He later flew Mustangs when the all-black unit escorted bombers in World War II.

WASHINGTON — Back before they called him a Tuskegee Airman, back before he wove himself into history, Jim Sheppard would have dismissed the question outright:

Sixty-six years ago, did he think it possible that in his lifetime, the commander in chief of the U.S. military would share his skin color?

"Well, there you said the key word – in my lifetime," replied Sheppard, 84, of South Portland. "And I would have to say no."

Yet there Sheppard sat Tuesday with nine of his old comrades, riding in style down the center of Pennsylvania Avenue.

And there in the reviewing stand outside the White House sat President Barack Obama, the nation's first black commander in chief.

"The No. 1 job?" Sheppard said, repeating the question. "I figured it was impossible with the resistance white people had against black progress in the United States."

He should know.

The first time he passed through this city, 18 years old and fresh out of Haaren Aviation High School in New York City, Jim Sheppard was anything but a VIP.

It was the start of World War II. Sheppard, newly inducted into the then-segregated U.S. Army, was on his way to the Tuskegee Air base in Alabama – not to fulfill his dream of becoming a fighter pilot, but rather to serve as an aviation mechanic.

Changing trains in Union Station, he and all the other black soldiers were ordered to sit in the front of the train because the air there, thick with fumes from the locomotive, wasn't considered fit for white folks to breathe.

"You had to be living back in those days to understand how it worked, because don't forget, discrimination was every day, everywhere," said Sheppard. "Every time you got on a bus or a train or a grocery store it was just there."

It was also there at Tuskegee, where then-President Franklin Roosevelt had ordered the creation of the 332nd Fighter Group, the first all-black unit in what was then the U.S. Army Air Corps.

Black and white?

It was that – and then some.

Sheppard remembers a white guy named Sgt. Torgenson who trained Sheppard at Tuskegee. They got to know each other pretty well as time passed. In another time and place, they might have considered themselves friends.

"But on weekends when we went into town, he'd pass by me on the street and not even look at me," Sheppard said. "It was like he didn't know me."

That would change – not just for Sheppard, but for all the black airmen from Tuskegee. The harder the whites tried to prove that "we couldn't cut it," Sheppard said, the more resolved the black airmen became to prove them wrong.

"We didn't just want to succeed. We wanted to be better," said Sheppard, who became a crew chief for the P-51 Mustangs, P-47 Thunderbolts, P-30s and Curtiss P-40s that the squadron learned to fly.

Oh, could they fly.

Deployed as bomber escorts in 1943 – first to Africa, and then, as the Germans retreated, on to Italy -- the 332nd flew more than 1,500 missions without once losing a bomber.

Their success, while tempered by the loss of 66 of their own pilots, helped persuade President Harry Truman to order the desegregation of the military in 1948.

"Everyone was trying to prove we couldn't do it," Sheppard said. "But we developed into one of the best fighter groups in the whole doggone Air Force."

A fat lot of good it did them. Returning home from Italy, Sheppard and his comrades walked off the troop ship and back into cold reality: White soldiers disembarked to the left, and blacks went to the right.

"We were better off in Italy," Sheppard said, shaking his head at the injustice of it all.

Most of the Tuskegee Airmen, unable to find jobs, left aviation forever. Sheppard worked as a postal carrier for five years before finally landing a job servicing Constellation luxury airliners at JFK International Airport in...