Editor’s note: This is the second story in a series exploring TEAM Westport’s essay contest for 2017. The first part of this series can be found www.westport-news.com and explored the media storm surrounding this year’s contest and the racist fallout. This story explores TEAM Westport’s leader Harold Bailey Jr. and his groundbreaking journey through life.

WESTPORT—Since gaining national attention, the TEAM (Together Effectively Achieving Multiculturalism) Westport essay competition on ‘white privilege’ has received heated and often intemperate views unleashed in emails and phones calls to local officials and Harold Bailey Jr., the chairman of TEAM Westport, the committee charged with celebrating the town’s cultural and ethnic mix.

Bailey, who attended high school in the South during the 1960s, is no stranger to the dark side of race relations.

Although he now lives in Westport, Bailey went to school in Knoxville, Tennessee when white privilege was the law. As one of 20 black students selected in 1963 to be the first sizable class to integrate into Fulton High School, Bailey, was bombarded daily with racial slurs, physical violence and threats of death. That year around 1 percent of black children in the South attended school with white children, according to ProPublica.

“They were saying the n-word all over the place…if you ended up in the hall alone you could get — I ended up getting — thrown against lockers and stuff like that. It was ugly,” Bailey said, adding that the cat-calls on the bus were a regular feature of life and “just outrageous.”

One day the waves of hateful and disrespectful rhetoric “got to be too much,” he said. When the bus got to the downtown where white and black students would disembark —the white students would then board a separate bus to their neighborhood and the black students would board a separate bus to theirs — a fight broke out and the students on a bus from Austin High School, the black high school, joined in the melee.

The next day at school, Bailey heard that some students from another white high school were planning on showing up to Fulton armed with zip guns — makeshift, homemade guns.

“We finally said that’s it,” he said. Bailey and his friend went to alert the principal who then told the assistant principal, a burly man. Both administrators took the threats seriously and it prompted the assistant principal to warn the white students at the school that nothing must happen.

That afternoon, it was announced that President John F. Kennedy, a man who championed integration for so many blacks, had been shot to death. As Bailey and his friends solemnly crossed the bridge to leave school that day — all devastated by the assassination of their president—that same assistant principal was standing there to protect them from harm, “literally with the longest switch which was like a branch and he was doing that to show nobody’s doing anything,” Bailey said.

The threat of imminent violence dissipated somewhat, but Bailey and his friends still heard someone shout “your leader is dead.”

The next year Bailey accepted a scholarship to Tilton School, a prep school in New Hampshire and eventually he went on to Brown University where he received a degree in Philosophy and Applied Mathematics.

“It was like an escape,” Bailey said of Tilton. “It took a long time to get used to—what you could say, what you couldn’t say. Because in the South there were certain ways you had to operate. I mean you couldn’t confront white people directly. Not if you wanted to survive.”

In the South, white privilege was based on law compared to Tilton and Brown where the disparity was more economic and predicated on what kinds of jobs Bailey would eventually be able to apply to.

“There were companies that weren’t hiring black people to do certain things,” he said.

Bailey came to be a Jackie Robinson of the corporate world. He broke barrier after barrier, rising to positions that had never been filled by anything but white people. He eventually became IBM’s Vice President of Lotus Marketing Integration.

By 1988, Bailey had moved to Westport and established himself as a pillar of the community. But that hasn’t protected him from the kinds of personal attacks that used to haunt his childhood.

One email came from a white male, who grew up in Bridgeport and worked at IBM, proudly signed his name after writing to Bailey directly: “And in this case, I’m 110 percent right to call out Baily as a hypocritical, scheming, race baiting n——r… “White privilege”? Why doesn’t the TEAM ask Baily how “black privilege” got him into IBM and got him promoted at IBM? IBM’s culture is so paranoid about race that blacks are regularly promoted no matter how little they know and regardless of their performance record. I learned early on in Bridgeport’s projects that black kids were the best actors, performers, manipulators, con artists, and practitioners of misdirection, in town.”

A white supremacist blog post called TEAM Westport a “Case Study in Anti-White Activism.”

Then there was the voicemail left on Bailey’s home phone number by a man who said: “So Mr. Bailey why don’t you do an essay on Mexican privilege? Why don’t you do an essay on Jewish privilege? Why don’t you do an essay on black privilege?...All you liberals want to attack white people and run your little psychological operation guilt trip on little white kids…You attack white people and you’re going to find out what happens. Things like this where we respond to your attacks.”

Despite facing rampant racism and hate when he was a student in the South, Bailey said the reaction from this essay contest has invoked a new type of hate—veiled hate.

“The difference now is you don’t know who these people are and it’s coming from literally all over the country…But when the emails hit, you have no idea and that’s a part of it that’s more troubling,” he said. “That they can hide.”

Asked if he regretted any part of this year’s essay prompt, Bailey responded with a confident, calm sense of purpose.

“No, not at all. Not at all. Because it needs to be taken on.”