Deported For An Old Crime, Jamaican Loses His American Dream

Howard Dean Bailey made a good life for himself in the U.S. But then, a decades-old run-in with the law led to his deportation. Does his story show the system failing or working?

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CELESTE HEADLEE, HOST:

This is TELL ME MORE from NPR News. I'm Celeste Headlee. Michel Martin is away. Now we turn to a personal story that highlights some sensitive issues in the immigration debate. Howard Dean Bailey emigrated from Jamaica as a teenager. And he was living the American dream - he was a business owner, a military veteran, a father, a husband. He became friendly with a fellow Jamaica who said he didn't have a private address in the area. So Bailey agreed to do him a favor - he let some of the friend's packages be delivered to his home. But it turns out the packages were filled with marijuana.

Bailey was arrested, his friend was not. And Bailey's lawyer advised him to take a plea deal. He ended up serving 15 months in a state work camp. Almost two decades later, that incident would scuttle his chances for citizenship. He was deported back to Jamaica with no money and only the clothes on his back. So is this a failure of the system, or proof that it's working as intended? Bailey's story was recently told in Politico magazine. He joins us on the phone from Jamaica, where he now lives. Welcome to the program.

HOWARD DEAN BAILEY: Thank you, Celeste.

HEADLEE: And also with us is Alisa Wellek, Mr. Bailey's attorney. She's also co-executive director of the Immigrant Defense Project. She joins us from our studios in New York City. Welcome to you as well, Alisa.

ALISA WELLEK: Thank you for having me.

HEADLEE: So Howard, maybe you could describe to us that moment when officers came to your door, and you were taken from your house to a detention center to be deported.

BAILEY: Well, that was just terrifying and unexpected. That morning was a terrible day, that's all I can say. For me, my family - it was just a day that will forever live in our memories.

HEADLEE: And you had applied for citizenship, and it had been pending for years, correct?

BAILEY: Yes, I had applied for citizenship in 2005. It was a long-delayed process. It went five years.

HEADLEE: And you were honest on your citizenship application, in which you revealed that you had had a run-in with the law.

BAILEY: Yes.

HEADLEE: And that's eventually what sunk your application.

BAILEY: Yes, I revealed that I had a run-in with the law.

HEADLEE: Alisa, what was the charge that ended up sinking Howard's application?

WELLEK: It was a drug offense. It was marijuana possession with intent to sell.

HEADLEE: How common is his story here? I mean, as I understand it - and you can correct me if I'm wrong - he had this charge, no one informed him when they asked him to plead guilty - and he did - that it might interfere with his ability to become a U.S. citizen. It was more than 20 years ago. He has two children who are both U.S. citizens. And he was, obviously, a business owner and a taxpayer. How common is this kind of situation where somebody gets deported? I mean, he was literally dropped off in another country that he hadn't seen for two decades.

WELLEK: Unfortunately, Howard's story really isn't an aberration. There's thousands of parents and green card holders and people who've been in the country for decades who have U.S.-citizen children, homes and families who are now facing deportation, or have been rounded up and deported. And many of those people are actually now the target of the Obama administration.

They're really going after people that had, you know, old convictions, often from decades prior and, you know, no second arrests, no other contact with the criminal justice system, to meet their numbers. And you know, once someone like Howard is in the deportation system, a judge's hands are tied. And they can't even consider the individual circumstances of his case - like the fact he was a veteran, the fact that he owned his home and had U.S.-citizen children and a business. So it's really a tragedy that thousands of people are facing.

HEADLEE: And I'm sure it's horrible. But at the same time, isn't that exactly the type of people that the Obama administration says they're focusing on deporting, is somebody with a record who spent time because of drug charges?

WELLEK: I mean, Howard is the type of person that the Obama administration is going after. But I think it speaks to the inhumanity and inefficiencies of the system. You know, we've kind of recognized on a national level, I think, that a lot of our drug policies have failed, that a lot of our mandatory sentencing policies have failed.

And even the attorney general has spoken out against that, in the criminal context. But in the immigration context, we're kind of stuck in time. And they're still really targeting folks that have been caught up in that.

HEADLEE: Howard, have you seen your wife or children since you were deported?

BAILEY: No, ma'am.

HEADLEE: How are you supporting yourself?

BAILEY: Well, basically, my family helps me out - my mom, my brother. You won't get no jobs in Jamaica, period. It's a country where unemployment is high. I'm considered a nobody because I was deported. So my chances of getting a job - none. So I tried pig farming, and that's not working out too well right now.

HEADLEE: Raising pigs?

BAILEY: Yes, ma'am.

HEADLEE: Alisa, what are the chances that Howard can have his day in court, that he can appeal this and eventually return to the United States to his wife and his children?

WELLEK: I mean, it's definitely an uphill battle. You know, most immigrants in Howard's case, like I said, never have the opportunity to have a judge consider or weigh any of the circumstances of their life. You know, all they can see is the mandatory automatic detention and deportation of that person. But we're trying our best.

You know, the Obama administration does have the power to alleviate some of the suffering both by Howard's family and, you know, the thousands of other families who are facing deportation and bring Howard back to the U.S. So we're trying to, you know, call upon the administration. We have a petition on our website, and we're trying to see if we can reopen his case.

HEADLEE: Howard, do you still have family members who live in Jamaica?

BAILEY: None that I grew up with or anyone that I am close with. Basically, right now I'm on my own.

HEADLEE: So moving forward, what kind of plans are you making? What if you don't return to the United States? Will your family join you? Will you - how does your future look?

BAILEY: It's a scary thing because actually, I don't see myself leaving the way it's going right now. I am just - I'm holding on to a whole lot of faith because even to this day, I still don't believe that I'm actually gone.

I feel like, any day now, I'm going to - I'm coming home. I don't know what the future holds, but I know this is not it for me right here. As far as the question, I don't know. I have nothing planned. All I want to do is to come home. There is no second option for me.

HEADLEE: Howard Dean Bailey is a deportee from the United States living now in his native Jamaica. Alisa Wellek is Howard Dean Bailey's attorney and co-executive director of the Immigrant Defense Project. Howard, good luck, and thank you.

BAILEY: Thank you so much.

HEADLEE: And thanks, Alisa.

WELLEK: Thank you.

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