Obama,The Latest Crossover Hero

Now, the sepia-toned candidate stands at the lectern. He is talking about the beginnings of this campaign, about his optimism. He says he has a plan to turn the economy around; he will bring the soldiers home. “This is why I am running for president of the United States of America.” Outside, in the sunshine, there are many wearing shirts festooned with the words “Yes We Can”  — uncannily reminiscent of Yes I Can, the title of the autobiography of entertainer, Sammy Davis Jr.

In the nightclubs of Los Angeles, in the mid-1940s, Sammy was known for hustling like hell. He was a young man in a hurry. Then, in 1954, in San Bernardino, California, Sammy crashed his Cadillac. One eye had to be removed. Acquaintances worried: would he be able to judge the distance to the edge of the stage with just one eye?

His comeback show was at Ciro’s, the famed nightclub. He wowed everyone. The trade publication Variety would gush: “It was Sammy Davis Jr.’s night. The lad who lost an eye came back in whirlwind style.”

He dreamed of the Great White Way, but many wondered if his nightclub act could sustain a Broadway show. Mr. Wonderful opened in 1956 and ran for more than a year, so did Golden Boy on Broadway in 1964.

He had an overbite, a pronounced nose, and the glass eye. In the 1960s, his wife was May Britt, the beautiful Swedish actress. At the White House, Sammy slept in the bedroom of the Great Emancipator.

But his boundless optimism didn’t overcome everything. Sammy once told writer Alex Haley of Roots,  “White cat sees you walking down the street, and he’s not even close enough to distinguish anything about you except that you’re not his colour — and just for that, right there, snap, bop, bap! That’s what makes you cry out inside, sometimes, ‘Damn, I wish I wasn’t black!’ “

Sammy steered clear of the Deep South. Not so the crooner Nat King Cole.

Cole — born in Alabama but raised in Chicago — was a child prodigy who formed a 14-piece band while still a teen-ager. In time Cole had a string of velvety songs that became popular. Husbands and wives and young couples swayed to Ramblin’ Rose, Sweet Lorraine and Mona Lisa.

In April 1956, Cole was booked into the Birmingham Municipal Auditorium in Alabama. Into Cole’s third number, a white man bolted from the back of the auditorium toward the stage. Within seconds, a half dozen members of the White Citizens Council were attacking Cole. Cole was left bloodied and wincing from an injured back.

So sometimes that lovely and indomitable optimism got stained with blood.

If one had to chronicle when the stylish black man in America landed upon mainstream consciousness, peruse 1944 Esquire Jazz Book. Inside its pages are photos of Duke Ellington and Count Basie, Coleman Hawkins and Cootie Williams, Dizzy Gillespie and Cab Calloway. All in lovely cotton suit, the natty white shirt, the hepcat tie. The music got them into white America.

Their success could be seen as furthering stereotypes: the black man and music, the black man and sports. And yet, Olympic gold medallist Jesse Owens was forced to race against horses for pocket money. “I wasn’t invited to shake hands with Hitler,” Owens once recalled, “but I wasn’t invited to the White House to shake hands with the president, either.”

In 1952, boxer Sugar Ray Robinson, confident that he had successfully crossed over, walked away from the fight game and went into show business. No other line of work, save entertainment, could earn him the kind of money he had made fighting. Still, there were limits. Robinson had to scurry back to the boxing ring to earn a living. When he died in 1989, Jesse Jackson gave the main eulogy, standing before those at Robinson’s funeral as an emblem of someone who also had made pioneering crossover leaps.

But Jackson, for all his rhetorical gifts, seemed weighed down at times by a sad history: halfway across the room is not the same as crossing over. Sometimes the wall of history seemed an inch high, and sometimes it seemed tall as the clouds.

Chicago was special to these crossover men as it is for Obama now.

Jesse Owens arrived there in 1949, got himself a job in public relations, did some jazz DJing for pocket money. Joe Louis strutted down Michigan Avenue in a long tweed coat. Billy Eckstine bought drinks over at the Drake Hotel. As a child, Nat King Cole  would walk around in a porkpie hat, carrying a Thanksgiving turkey. And, Sugar Ray Robinson defeated Jake LaMotta on Valentine’s Day 1951 at Chicago Stadium.

Now there’s another man standing in queue. There he goes, another Chicago man seeking the hearts of America, trailing complicated ghosts.