In early 2007, Karey Lee Woolsey received a frantic phone call from his girlfriend saying that she had received a summons to appear before a Federal Grand Jury about drug activities in the Ft. Myers, FL area. Activities that Woolsey knew included him. The two met and Woolsey had some advice for the young woman: 

"You can t say I did anything wrong. You are not going to lie just tell them you didn t f -g know. Get yourself an attorney." 

The conversation was taped. The girlfriend was cooperating with the federal Drug Enforcement Agency, who viewed Woolsey s comments at witness tampering and confirmation of his involvement in drug distribution. 

On September 20, 2007, Woolsey was arrested by federal agents on charges that he had been a part of a large drug ring based out of Ft. Myers, FL. The drug? Marijuana. The amount? 1,000 kilos distributed over a four and half year period. While it might seem that that is a lot of pot, it should be noted that Woolsey had no pot on him at the time of his arrest. In the Federal Sentencing Guidelines there is a term, "Relevant Conduct," which does not require that Woolsey have any drugs on him in order to arrest him. It only requires that other people, cooperating with the government, say that they bought drugs from Woolsey. It might be hard to believe but that s how we roll here in the U.S.: 

Relevant conduct, as it is now defined, can include uncharged conduct, acquitted conduct, conduct described in dismissed counts, and conduct of co-conspirators. 

And we wonder why prisons are overcrowded. I digress. 

So when the amount of marijuana was calculated in the case (people x how much they said they purchased x the number of months they knew Karey = 1,000 kilos), Woolsey realized that fighting these charges could land him in prison for the rest of his life. He pleaded guilty in January 2008 and hoped that his clean record (no prior arrests) and throwing himself on the mercy of the court would lead to a much lower sentence. He would be wrong. In August 2008, U.S. District Judge John E. Steele (Middle District of Florida) sentenced Woolsey to 151 months in federal prison. For those of you without a calculator, that is 12 years and 7 months. 

That arrest and subsequent prison term interrupted a music career in its infancy for the then 32 year old Woolsey. In his indictment, it listed Woolsey as "a/k/a Musico ", a nickname attributed to his love of music and his aspirations to make it as a professional musician. His mother wrote me saying of Karey; 

He writes his own lyrics and music, sings, plays guitar and piano. He was a fairly well known talent in our little Ft Myers, FL community. He desired to live a rock star life on a small income so he also had a small t-shirt company, he invested in real estate and was very ambitious. He also lacked patience in waiting for his other endeavors to pay off significantly to Karey it [selling marijuana] seemed like just another opportunity to support his band and enough money to travel so he could have more chances to become well known in a larger market for his musical talents. 

We may have never known of Woolsey s talent had he not laid down a few scores prior to prison. After pleading guilty and awaiting sentencing, Woolsey rounded up what money he had and used it to record an album, "A Million Miles Away" under the name Karey Lee . It was released this past July. Like a message in a bottle, Woolsey taped his music and hoped that someone would "discover" it while he was in prison. While Sony SNE +1.39% did not call, a friend from his past did. 

The music stands on its own but Woolsey would not have been able to pull it all off it had not been for his good friend and representative in the free world, Sarah Castellano. Castellano was searching on Facebook FB -4.11% in 2010 when she found an old friend from middle school, Karey Lee Woolsey. She discovered information about his case and remembered him being such a wonderful person, so she decided to reach out to him in prison.. The two rekindled their friendship and the more Castellano visited, the more the two became motivated to work on releasing Woolsey s music. "In the beginning, I had no idea what I was doing," Castellano told me in an interview, "but I was determined to help Karey as much as he helped me." Since the decision to move forward with the album s release Castellano has acted as agent and PR manager. 

So how have others received his music? Billboard Biz s ranking of independent artists put his album at #4 after its release. Not bad for a guy who cannot tour, gets no play on the radio and is currently in federal prison. Not bad? It is an amazing accomplishment! Songs from the album are available on iTunes, Amazon and other digital music outlets. While I m no music critic, his sound is unique and a review I found on line captured the essence of his story and style. His songs are part of my own iTunes collection with my favorite being "These Walls Around Me." 

Still writing in prison, Woolsey has not let the time go to waste. Drawing inspiration from his prison life, he wrote a song about a man who was about to be released from federal prison after serving 30 years. The words to "30 Years" tell a moving story of an older man contemplating life after prison: 

So tell me where do you want me to go? 

I honestly have no other home. 

Maybe you could shine a light 
And tell me everything will be alright cause 

It seems to be after 30 years 

Everyone just disappears 

LA's Redemption Foods, Serving Up "Hope" 
Walter Pavlo 
According to Woolsey, songs are just are part of his prison life. Writing me from prison, he said, " If I write a song and it doesn t get stuck in my head for at least few days, I will trash it. I have been walking around for the past month with all these different songs in my head It really drives me crazy, but its what I do." 

I am sure that Woolsey is wondering what awaits him one day, outside of those prison walls. Perhaps a big time promoter like Simon Cowell, who has taken a hit to his image as a result of a tryst with his good friend s wife, will give a guy like Woolsey a break. It would make for a redemptive headline. 

Woolsey is currently incarcerated in the low security federal prison in Yazoo City, MS. His release date is set for July 2019. He will be 43 years old. 

To keep up with Woolsey, since you won t be seeing him on The Voice anytime soon, take a look at his Facebook page or, which is updated by Castellano. 

I wrote about Karey Lee Woolsey in August 2013.  Woolsey is now hoping that recent changes to federal drug sentences will send him home a few years earlier than his current expected release in 2017.  He has already been in prison for seven years on marijuana charges.  A drug that may be legal across the country by the time he is released!

Woolsey, a talented musician, recently sent a newsletter to his family, friends and fans about his time in prison and his reflections on those seven years.    With permission from Woolsey, we are sharing it here:


SO what’s going on? Man …time is hauling serious ass. I have been in this RDAP [drug abuse program offered by Bureau of Prisons] program for 4 months already  (5 months to go) It’s going pretty well. They talk a lot about different behaviors and ways to adapt back into society. I really don’t think I’m going to have a problem with that. Even though I have never seen a touch screen phone before, I bet I transition back into the real world pretty well. I can’t believe I have been gone 7 years. It sure doesn’t seem that long.

 So my little brother Kodey and his wife AJ had a little boy and named him Tannin. Yes I’m an uncle again  :) . He is soooo cute, my brother sent me pictures of his cute little baby feet. I LOVE BABIES FEET!! He won’t ever know I was gone which really makes me feel good.

Kodey had Kayden before I left (his oldest  boy) and he was  a newborn …so its so weird seeing him all grown now days when he comes to visit.

When you’re in prison its like you have a time machine. You don’t really see details …of anything. Like for instance… One of my buddies was married for 6 years since I got out. Then got divorced  ..and now he’s married again to a different women. I keep thinking that his first marriage is the same women …Its crazy. I REALLY have to be careful! I could get him in SERIOUS trouble…HA!!  



When I left my daughter Miracle was 10 years old…had just turned 10. In a few months she will be 18. Its kind of sad, but at the same time…I sort of feel like life gave me a second chance ya know. I have had 13 of my friends pass away since I have been gone, So I just consider myself lucky and blessed.

I have some great music to be recorded. I’m telling you …I’m writing some monsters and the world is going to hear all about it. I’m going to do some great things when I get home…I just want to start already. Dang…I have learned my lesson…I learned it 7 years ago in county jail for Christ sakes!

So what about American Idol ?? I think Clark has a GREAT voice …I think he’s my favorite …he needs to relax a little bit but he’s one talented dude.

OHHHHHHH…I have been playing a lot of BBQ’s and stuff for the prison here….The cool thing about a prison gig is you are guaranteed a good crowd! HA!!  A couple thousand people show up READY TO JAM!!  HA!! Well ….its true!!! Our last gig was pretty cool. They closed the prison down and let us play in the middle of it. It was the first time in history that they have done this. I think the warden may be a fan. Also. I always play my originals which is pretty cool.  The band all sorts of cases of ice creams and extra burgers and waters…I know that doesn’t seem like much my friends…but in prison…A bottle of water is rare. Also …some ice cream!! FORGET ABOUT IT!! HA!!

I have two more gigs this month here…I’m playing an expo that they are putting on for RDAP next week. Then I’m playing the RDAP graduation the following week. My band is actually pretty good. We don’t get enough practice but we have a lot of fun. A lot of benefits come with being the entertainment for the prison.

Like I say …It could be sooooooooooooo much worse.


I’m ready to come home. and to play music for the free world. I have been here long enough….I miss all you guys …my Facebook has been kind of distant …but I’ve  been soooo busy in here. Please be good to yourselves …and PLEASE …stay out of trouble.

We all need to understand more about the people we incarcerate if there is any hope of reforming a prison system that has become a burden to our government and society.  This note from Woolsey captured everything that I know about people in prison … their joy, their hopes, their dreams, and their families.

Reform should start by looking at the people in our prisons and not at the laws that put them there.  Once we see the people, the laws will change quickly … for the better.




In the middle of a scorching Mississippi summer, he sits outside, pencil in hand.

Across the yard, there is a basketball game going on. The thump, thump, thump of the ball hitting blistering pavement doesn’t distract him. He’s in his bliss.

Words flow, coming from a deep well of despair that overflowed and turned into acceptance, and then into hope.

These songs of redemption, with titles such as “These Walls Around Me” and “Busted,” make up the album “A Million Miles Away,” to be released Tuesday even though their writer and singer, Karey Lee Woolsey, sits in a federal prison.

Dreams on hold
It was July 19, 2007. Woolsey was happy. He had just turned 31 and was engaged to the girl of his dreams. He was running the popular Martini’s Rock Club in downtown Cape Coral. He was preparing to write new songs and get serious about his first love — music.

Then came the phone call from an ex-girlfriend. A call that changed his life and put everything on hold.

She was hysterical. Something about agents from the Drug Enforcement Agency. Lots of questions.

“I’m in trouble,” he thought.

He drove to meet her at a Publix parking lot near Plantation Road in south Fort Myers.
They sat in her car, but it wasn’t to talk about what might have been or even to catch up like old friends. Tears rolled down her cheeks. She was terrified, visibly shaking. She handed him a piece of paper.

She would testify against him in court, it read.

Woolsey was sick to his stomach. “There isn’t a feeling like it in the world. It’s like being told you have a certain amount of time to live.”

From there, it seemed to spiral out of control. She started asking him questions that he felt were none of her business. Each question got a vague answer, but it was enough.

“You need to tell them you don’t know anything…”

“You can’t say I did anything wrong…”

“You don’t know that I laundered money…”

What he didn’t know at the time was that she was wearing a wire, a pawn in the Drug Enforcement Agency’s game to nab their suspect.

They got their guy, and because of his exchange with her, were able to add witness tampering to a long list of offenses, 16 counts in all.

Woolsey was no longer selling at this point, those days long behind him, he said. The federal indictment states that he committed the crimes from August 2002 through January 2006.

But the past caught up to him, and a little more than a year later, his journey of repentance and self-renewal began.

Adjusting to a new life
Yazoo City Low sits in the Mississippi Delta, about 36 miles north of Jackson.

It’s part of the three-facility Federal Correctional Institution complex that houses minimum to medium security male offenders. The Haley Barbour Parkway runs to its east and one of the city’s many rivers snakes around to its west.

When Woolsey arrived in early August 2009, he went through the mandatory orientation and eventually joined more than 1,800 other inmates. His name came with a number: 34411-018.

Gone were the jeans and tees, replaced by a khaki prison uniform. He was a 13-year victim of his “dumb mistake.”

The federal justice system has “truth in sentencing,” which means inmates serve nearly all the time to which they are sentenced, and there is no parole.Thirteen of the 16 counts he faced were dropped. He took a plea deal on the remaining charges: conspiracy to sell marijuana, witness tampering and money laundering.

On Aug. 4, 2008, in front of a packed courtroom at the federal courthouse in downtown Fort Myers, Judge John E. Steele sentenced him to nearly 13 years. Projected release: July 17, 2019.

Does he feel he got a harsh deal? “Sure I do, but that’s life, right? Sometimes it’s harsh, but when you get knocked down, you dust yourself off and you get back up, learn from your mistake and try again.”

He thinks three years in prison and some healthy fines would have been more fitting for the crime, and said that spending one day in the Lee County Jail — which he calls “rough” — was enough to make him decide to never break the law again.

Woolsey said the federal conviction rate is high, which is why he and his attorney chose to take a plea deal.

He said all of his Yazoo friends are in on drug charges. His former cellmate, Johnathan Kohrs, 27, served six years for trafficking in marijuana. He was released last year and lives in Missouri, where he sells real estate.

Kohrs said Woolsey was the first one to talk to him and make sure he had everything he needed. “It was such a blessing to have met him and become as close to him and his family the way I did.”

Woolsey said his family is closer than ever, the heartbreak having tightened their bond.

Linda Foster, his mother, still puts presents for her son under the Christmas tree, so on his first Christmas at home, he’ll have them to open.

“Christmas has always been a special time for our family, gathering around the tree and everyone exchanging gifts,” Foster said. The first Christmas without her son was one of the hardest times her family has ever faced. She also includes gifts for Daniel Sweep, Woolsey’s co-conspirator whom the family remains close to.

Woolsey also has two daughters. His oldest, Logan, 20, lives in South Carolina. Miracle, 15, lives in Cape Coral with her mother.

He said he misses privacy the most. He misses having a nice bed. The bunk beds they sleep on in their dorm-style units are about as hard as the floor. He has one blanket and a pillow the size of a small towel.

He misses his recording studio and its equipment.

Making music, peace
Foster said Woolsey started writing songs when he was little. He would make up silly songs and teach them to his brothers and then perform for his parents.

She gave him a guitar when he was 13. He taught himself to play it, locking himself in his bedroom for hours as he learned the chords.

“I hated how it was hard for me to play in front of people,” he said.

Foster discovered her son’s talent in a startling way. She could hear the Black Crowes’ “She Talks to Angels” coming from his bedroom and went to tell him to turn the radio down.

Embarrassed and surprised, he threw his guitar down when she entered.

“Was that you?” she asked, nearly in tears.

She asked him to play it for her again. It was one of the most beautiful things she’d ever heard.

From then on, he was free to play his music as loud as he wanted.

At 13, Woolsey wrote “The Silence” and “Might Die.” He assembled a band he called Sweet Madhouse. They put down “The Silence” on an old 4-track recorder, then sent the tape to radio station 96K-Rock. The deejay, Mike Holiday, liked it so much he played it on air, sending Sweet Madhouse into hysterics.

“I kept thinking about what kind of house I was going to buy my mom,” he said.

After that, he wanted to record a real rock album — at age 14.

His parents loaned him money to rent the Firemen’s Hall in Cape Coral to put on a show. It sold out — about 500 people were there to hear Woolsey perform original songs. He paid his parents back by selling soda and made about $2,000, which he used to buy new recording equipment so his band could make their first demo.

“After that gig, I knew that playing music was what I wanted to do for the rest of my life.”

Songwriting made adjusting to prison life easier.

“I know that if it wasn’t for my music, I would not mentally be where I am at now.”

Woolsey has realized he was put on earth to write music. He has written more than 100 songs while incarcerated. He transcribes the songs note by note and then sends them home to Foster, who copyrights them with the Library of Congress.(Page 5 of 6)

“The worse the day, the better the song,” he said.

Then there are the prison concerts. Woolsey plays the drug-program graduations and the annual hip-hop show, where the inmates get together and rap. Woolsey opens the show — the lone non-rapper.

“You see this crazy white boy singing his heart out in front of a thousand or so hard-core rappers, it’s awesome.”

He said playing for inmates can be emotional because they’re lonely and miss the outside world.

“The vibe is so heartfelt and poignant. It’s like nothing you have ever felt before. It’s one of the most surreal feelings.”

Most of the songs on “A Million Miles Away” were written while he was on bond, awaiting sentencing.

“I had about nine months until I had to go to court and from there, I was going to prison.”

Former 99X radio personality Jeff Zito said Woolsey is talented and very driven, and despite being in prison, he could make it. He referenced Woolsey’s former band, Simply Smut, which opened for some big acts, including Creed and 3 Doors Down. “If he could do it then, he can do it now,” Zito said.

He thinks that Woolsey is marketable because he has a good story to tell. And he doesn’t think being imprisoned will hurt Woolsey’s reputation. “When it’s rock and roll, these things tend to be forgiven a little easier,” Zito said.

Woolsey said his new album takes the listener on a journey into the mind of a man who’s about to go to prison and trying to make peace with himself.

“At one point of my life, it did seem like I was a million miles away from everyone and everything. I’m over halfway done with my journey now and I’m starting to see the light at the end of the tunnel.”

What lies ahead
Woolsey may be released in 2017, if he successfully completes the drug treatment program that is a requirement of his sentence. The 10-month intensive program teaches inmates how to cope with life without using or selling drugs. Only inmates 36 months from release are allowed to participate, and those inmates get a year shaved off their sentence.“They say the last year in prison is the hardest … I bet when you are finally on that last year, the seconds turn into hours and months probably seem like years,” he said.

He’s looking forward to the unknown of a new life.

He doesn’t think he’ll have trouble getting a job after prison. “I have a very good business sense. I love creating ideas and then bringing them to life and seeing them operate … I’m ready to get out there and work.”

While he hopes his music career will take off, he isn’t opposed to writing songs for or producing other artists.

He said he’ll never try to forget about life in prison. “Part of where you’re going is remembering where you’re coming from.”

“This is a place I will never come back to, and the memories will always help remind me to make the right decisions in my life. Better decisions. Decisions that continue to make me a better person. Sure, I have a lot to prove, but I also have a lot of life left to prove it. I am so ready.”

The day he’s released will be one of the happiest days of his life. It gives him chills to think about.

“I am such a different person now. It’s funny. Everyone said to me before I left to never change, and I really was trying not to. But if they liked the person I was, they will love who I’ve become.”

The phrase, "A million miles away," can have so many different meanings depending on how the expression is used. For Karey Lee Woolsey, a current pot prisoner, the term speaks volumes to his current situation: he's doing a 13-year bid at the Federal Correctional Complex in Yazoo City, Mississippi 35 miles north of Jackson. Woolsey also uses the idiom as the name of his debut album, a 13-track project released July 9.

Woolsey was a professional musician in the Cape Coral, Florida area playing up to 250 gigs a year before his 2007 arrest on charges of conspiracy and possession with the intent to distribute more than 1,000 kilograms of marijuana, plus 13 counts of money laundering and one of witness tampering.

His fall from fame was made possible in part by an associate getting popped and rolling on Woolsey, claiming him as a co-conspirator in the local marijuana trade. Woolsey, no longer in the game, was preparing to write new songs and focus on his music when he received a frantic call from his fiance, who asked him to meet her in a Fort Myers Publix parking lot. Once the pair was face to face, she told him that she was going to testify against him in court. Not knowing she was wearing a wire, Woolsey said, "You need to tell them you don’t know anything… You can’t say I did anything wrong… You don’t know that I laundered money," giving the DEA the last piece of puzzle.


Knowing that his crimes would carry a minimum 10-year sentence, Woolsey was determined to record an album before his incarceration. That album, 
A Million Miles Away, is a story of redemption. From start to finish Woolsey takes the listener on a journey through the eyes of a man looking at spending a tenth of his life behind bars and manning up for what he did. 

The opening track, "These Walls Around Me" (see clip below), is a blueprint of a man having to leave behind everyone and everything you have ever loved. "That song was a goodbye to my old life," Woolsey tells Celebstoner via email. "I knew I was heading to prison for a while, and I just wanted people to know that I would be back one day, and better than ever." The cut features Woolsey's infectious piano playing and a hooky chorus.

A couple of the songs on A Million Miles Away sound reminiscent of other mainstream bands. "Get Up and Drive," with a peppy beat and groovy rock riff, produces a pedal-driving anthem you can find on any New Found Glory disc. On the R&B ballad, "Only In My Dreams," Woolsey reveals his inner Prince with a slow jam about finding one's true dream girl. "I wrote the song in my sleep one night, and In the dream I was playing with Prince," he explains. "It's usually not my music style of a song, but since I was singing with Prince in my dream, I put that R&B spin on it."

Other notable tunes include "God," "Fall in You," "Busted" and "Freedom." Woolsey wrote the latter song in county lock-up. "It was one of my darkest moments," he says. "This was me. So scared to be honest. Leaving for prison, knowing that my life would forever be changed. I had a choice. Tell on everyone and get time cut, or face the music. I decided to face the music. This is the ONLY thing I don't regret. I sleep better, and will again one day have my FREEDOM. Freedom... What a powerful word."

Before becoming federal prisoner #34411-018, Woolsey was a member of various Florida bands, including Sweet Madhouse, SMUT, 3 Days Apart and Licensed Sex Therapist. They play various dives and VFW halls, but also opened for Alice In Chains, 3 Doors Down and Sister Hazel.

Since the release of A Million Miles Away, Woolsey has made headlines around the world due to digital sales on various and iTunes charts. But for Woolsey, all that glitters ain't gold because no matter how successful the CD is he will still be locked up for another eight years. Doing his prison jobs - providing sound for the prison live events and participating in a leather craft program - helps him pass the time. Woolsey's personal mission is "to bring to light the flawed marijuana laws in this country. Let's be allowed to make mistakes, but if you can use your mistakes to help create a better way for the next person then don't be afraid to do so. No matter how far you think you are from something in your life it's always within reach. Even when it may seem like it's a million miles away."

A Cape Coral man who released an album despite being incarcerated in federal prison has reached the Billboard charts.

Karey Lee Woolsey’s “A Million Miles Away,” released July 9, was ranked fouth on Billboard’s Heatseekers South Atlantic chart, which ranks the week’s top-selling albums by new or developing acts.

Woolsey was thrilled. “I swear I can’t believe it,” he said.

The album is selling on iTunes, and, where it ranked as high as third in Adult Alternative sales the week it was released. Billboard compiles its Heatseekers based on Nielsen SoundScan data, which tracks music downloads. Many artists who appear on the Heatseekers chart eventually land on the Billboard 200 or Hot 100 charts.

“We knew something was going on when Amazon informed us that it was No. 3 three in the nation last Friday,” Woolsey said. “I couldn’t sleep that night. Then the next day it was No. 2 and it just took off from there.”

Woolsey is serving a 13-year sentence at the federal priison in Yazoo City, Miss. He began serving in 2009 after taking a plea deal on charges of trafficking in marijuana, money laundering and witness tampering. His projected release is 2019, though he may get out in 2017.

Most of the songs on the album were written while Woolsey was awaiting sentencing. He recorded the album before he went to prison, but it wasn’t until this year, when the spotlight on legalizing marijuana began to heat up, that he decided to release it.

“I’m not screaming for legalization here. I’m wanting to make the federal laws make a little more sense,” he told The News-Press in June. “I’m a perfect example of why the federal government needs to change the laws.”

His manager, Sarah Castellano, said profits from the sales of the album go to the “Free Karey Lee” organization, which she and Woolsey started to bring attention to what they call harsh laws.

Castellano is pleased with the album’s success, given that there hasn’t been any airplay or that Woolsey isn’t able to tour.

Woolsey remains modest.

“I think people know that I screwed up, and I’m just trying to be a better person and show the world that you can achieve your dreams and goals without having to take the shortcut in life,” he said.

Karey Lee From The Inside

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