"Lindsay, I am speaking to you today as not just a prison minister and friend of your father but as a person who has traveled down the same road you are on," writes Angelo in a letter released Thursday. "I know what works and through God's grace, mercy and love have been straight for 30 years."
Angelo's attempts at reaching Lohan began when the actress' father, Michael Lohan, contacted him in 2007 to help his daughter. Michael Lohan had read Angelo's book, Once Life Matters: A New Beginning, which he said changed his life while he was in prison.
Since then, Angelo has been sending the younger Lohan letters and books and has personally accompanied her father to court appearances in the hopes of getting her enrolled in a faith-based programme.
Angelo is no stranger to the celebrity life and substance abuse.
In an interview with The Christian Post he shared: "I was in the entertainment industry for 15 years. I got my start with Jimmy Hendrix, George Harrison, John Lennon, Janis Joplin. I was working in the business when no one that was doing drugs had any consequences. It was only when Janis died and all of a sudden I kept getting arrested – I got arrested in Miami with four ounces of cocaine in my pocket – [that I realised I needed to change]."
He said he is compelled to share Jesus with these celebrities when he sees the pitfalls of his youth paralleled in Lohan's and other troubled stars' lives.
"I had the same problem, back in the 60s and 70s. I feel somewhat of an obligation to reaching out to them and telling them about Jesus. I've been trying over the last four years to convince her (Lohan) that Jesus can change her life."
Angelo emphasised that secular rehab programmes cause little to no change in a person fighting substance abuse. He mentioned that a recent study from UCLA showed that people struggling with substance abuse who went to a rehab programme did worse than those who did not go to a programme.
"I'm talking about a programme that can change her life. Not a secular 30-day programme that she's gone in that just takes her money and she comes out the same way she went in," said Angelo. "Maybe it cleaned her for a little while but then of course the temptation is still there."
Lohan, 24, is known to have checked herself into five different rehab programmes. While she had previously claimed a positive feedback, she failed a drug test just days later and publicly posted on Twitter, "Regrettably, I did in fact fail my most recent drug test and if I am asked, I am prepared to appear before Judge Fox next week as a result."
On Wednesday, the "Mean Girls" star pleaded not guilty to charges of grand felony theft for allegedly stealing a $2,500 necklace from a store in Venice, California, on January 22.
Prior to her court appearance, the Catholic-raised actress had asked her friends to "pray for her".
Angelo reminds Lohan that while most media are only looking at her mistakes, he only looks at the ways God can be glorified through all her troubles.
"[Media] feels justified judging her but who is going to cast the first stone? Which one of us is not a sinner?"
Although he finds it unfortunate that some consider her as "the poster child of America's troubled youth", he wants to assure her that there is hope. But first she needs to repent and then get away from the industry for a year.
"She should repent. She needs to take a break from that whole industry that she's in. It glorifies that lifestyle that they are so used to that. That's why I said a 12-month faith-based programme would get her started," he said.
Angelo emphasised that the first step in the programme would be "introducing her to Christ".
While he is still in contact with her father, Angelo will continue to try and reach out to her and other troubled celebrities, including Paris Hilton. He is currently offering his book for free to those in prison and rehab programmes and to troubled celebrities.