How to Mentor Youth by St. Vincent MacKenna

Yesterday, I spoked at Riverview Community Church in Santee. (About 20 minutes from my house) While I do a fair amount of speaking in churches and schools I’m almost never asked to present brand new material, so it was a fun challenge for me, a throwback to working in the local church and creating brand new stuff all the time.

I was asked to do part 2 in their series, Redbox at Riverview, where they take a look at a recent movie and explore a spiritual principle. In my case, I was asked to teach on mentoring youth from the vantage point of St. Vincent.

Note: These are my teaching notes, so not exactly a full manuscript, I’ll post the podcast when it’s available. My slides are included and I’ve added the clipping times for the videos I used. (They are copyrighted videos, so obviously I can’t post those.)

 Scripture Reading – 2 Timothy 1:1-5

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 Paul, an apostle of Christ Jesus by the will of God, in keeping with the promise of life that is in Christ Jesus, To Timothy, my dear son:

Grace, mercy and peace from God the Father and Christ Jesus our Lord. I thank God, whom I serve, as my ancestors did, with a clear conscience, as night and day I constantly remember you in my prayers. Recalling your tears, I long to see you, so that I may be filled with joy. I am reminded of your sincere faith, which first lived in your grandmother Lois and in your mother Eunice and, I am persuaded, now lives in you also.


This morning we’re going to look at two relationships… 

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First century Apostle Paul and first century pastor Timothy


A fictional relationship between a 60-something year old Vincent MacKenna played by Bill Murray and an early adolescent boy named Oliver.

Let’s start with Paul and Timothy, shall we?

Context of 2 Timothy

  • Author – Paul wrote 1 & 2 Timothy when he was imprisoned under Nero, 66-67 AD. In the past, when Paul was put in prison, he was really under house arrest and stayed in a rented house. But this time he was chained to a wall… his friends had a hard time locating him… and it was clear that Rome was about to kill him. So 2 Timothy serves as Paul’s last words to Timothy.
  • About Ephesus – Ephesus was a big, important city, capital of the province. It’s most known as the home to the Temple of Diana (Artemis) Paul knew the city well, he’s started Timothy’s church… before silversmith’s ran him out of town! (Acts 19:23-29)
  • Timothy’s church – Timothy was the pastor of the church in Ephesus. He was a young, new pastor leading an established church. In Paul’s mind, his last words to Timothy were really also last words to the church… one he loved.
  • How Paul met Timothy – (Acts 16:1-3) “Paul came to Derbe and then to Lystra, where a disciple named Timothy lived, whose mother was Jewish and a believer but whose father was a Greek. The believers at Lystra and Iconium spoke well of him. Paul wanted to take him along on the journey, so he circumcised him because of the Jews who lived in that area, for they all knew that his father was a Greek.”
  • Their relationship – Basically, Timothy was the son Paul never had. Paul worked with a lot of people in his life, trained a lot of pastors… but Timothy always had a special spot.
  • Paul’s hopes for Timothy – All of 2 Timothy, his final words to his protege, are filled with instructions to KEEP GOING and to PREACH THE GOSPEL BOLDLY.
  • and Timothy’s troubles – 1 Timothy addresses some of the problems being faced specifically… but mostly Timothy had to deal with older people in the church not trusting him because he was young… probably under 30… and there were some Christians in the area teaching that Jesus had already returned.

Introduction of St. Vincent (the movie)

Today we’re going to look at the film St. Vincent.

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Here’s the official description I stole from IMDB:

Vincent is an old Vietnam vet whose stubbornly hedonistic ways have left him without money or a future. Things change when his new next-door neighbor’s son, Oliver, needs a babysitter and Vince is willing enough for a fee. From that self-serving act, an unexpected friendship forms as Vincent and Oliver find so much of each other’s needs through each other. As Vincent mentors Oliver in street survival and other worldly ways, Oliver begins to see more in the old man than just his foibles. When life takes a turn for the worse for Vincent, both them find the best in each other than no one around them suspects.

Let’s start off by meeting our protagonist… Oliver.

It’s Oliver’s first day at a new school. He and his mom just moved to town to start a new life… 

VIDEO: Meet Oliver – (short version) 11:08 – 14:13

Now Let’s Meet St. Vincent of Sheepshead Bay

Video: Vincent Meets Oliver – 19:16 – 21:48 (long version)

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Vincent is…

  • Exceedingly grumpy
  • Probably an alcoholic
  • Smokes a lot of cigarettes
  • Has a gambling problem
  • Is married… but has a relationship with “a woman of the night” – a pregnant stripper

Contrast that to his namesake… Let’s meet St. Vincent de Paul

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  • For our Catholic friends, St. Vincent de Paul is the patron saint of charitable societies
  • Born in 1580, France.
  • He became a priest in 1600.
  • Shipwrecked at 25 years old, enslaved in Africa for 2 years, he later escaped
  • Upon his return he served as a priest with wealthy Parisian families, which opened doors for him to do use his benefactors wealth, properties, and influence to serve the poor, the sick, and imprisoned.
  • During his lifetime many missions, hospitals, and charities were begun, including the society that bear his name and currently runs Father Joe’s Village in downtown San Diego.
  • St. John’s, Niagara University, and DePaul University in Chicago were all started by the Congregation of the Mission founded by Vincent de Paul. (An order of the priesthood within the Catholic Church)
  • St. Vincent de Paul is a big deal!

When you look at Vincent of Sheepshead Bay you see the exact opposite of St. Vincent de Paul.

He is a mess. But he’s our main character…

And as circumstances would have it, he’s just gotten himself hired to mentor the boy next door.

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Back to Paul & Timothy

Paul is an unlikely example of the perfect mentor…

  • First encounter with PaulActs 7:57-60 – He oversaw the first martyrdom of a Christian –  “At this they covered their ears and, yelling at the top of their voices, they all rushed at him, dragged him out of the city and began to stone him. Meanwhile, the witnesses laid their coats at the feet of a young man named Saul. While they were stoning him, Stephen prayed, “Lord Jesus, receive my spirit.” Then he fell on his knees and cried out, “Lord, do not hold this sin against them.” When he had said this, he fell asleep.
  • He wasn’t just against Christians, he spent years of his life persecuting Christians. (Acts 9:1-2) “Saul was still breathing out murderous threats against the Lord’s disciples.He went to the high priest and asked him for letters to the synagogues in Damascus, so that if he found any there who belonged to the Way, whether men or women, he might take them as prisoners to Jerusalem.
  • Skipping forward — Years after his conversion, his first attempt at having a protege ended badly – He’d done two long trips with his best friend Barnabas… but their relationship ended over a young man named John Mark. (Acts 15:37-41) “Barnabas wanted to take John, also called Mark, with them, but Paul did not think it wise to take him, because he had deserted them in Pamphylia and had not continued with them in the work. They had such a sharp disagreement that they parted company. Barnabas took Mark and sailed for Cyprus, but Paul chose Silas and left, commended by the believers to the grace of the Lord. He went through Syria and Cilicia, strengthening the churches.
  • So you can imagine what everyone would have thought when they heard about Timothy just a few months later!
    • This won’t last… it’ll be a disaster…
    • Silas is probably going to leave Paul, too
    • Paul is great… but the dude has issues!

But none of those worries panned out. Instead, just like between Oliver and Vincent, this messy man starts to wear off on Timothy in all of the right ways.

Which leads us to…

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Rule #1 of mentoring…

Mentoring youth is messy and best left to messy, imperfect people.

Video: Who taught you to slap? – 32:30 – 33:20

Let’s take a moment to imagine the Apostle Paul and his traveling companion Silas talking in their tent… Acts 16 says..

“Paul came to Derbe and then to Lystra, where a disciple named Timothy lived, whose mother was Jewish and a believer but whose father was a Greek. The believers at Lystra and Iconium spoke well of him. Paul wanted to take him along on the journey” 

So let’s imagine a conversation about Paul’s idea of taking Timothy with them…

Paul: Hey Silas, bet you didn’t think we could set up the tent with just the two of us…

Silas: Really, Paul? You’re going to bring this up when you know why it was so hard… you and your fat mouth are the reason John Mark and Barnabas aren’t here to help.

Paul: Yeah, that’s my point. We need help.

Silas: We had help… you don’t play well with others. Remember?

Paul: I heard good things about this kid, Timothy, today. He comes from a good Jewish home.

Silas: Well… not good enough. They didn’t even get him circumcised.

Paul: Yeah, well… I can probably talk him into that. What do you think?

Silas: I guess… I mean… if he’s willing to get circumcised he’s probably going to be able to put up with you…

So that’s probably kind of what Paul’s first impression of Timothy was. Probably, not much. But long term? Paul made an incredible impression on Timothy and Timothy made an incredible impression on Paul.

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Rule #2

First impressions are never as important as lasting impressions.

Let’s get back to Vincent and Oliver.

Video: First Impressions – 24:49 – 25:51

Their relationship started as a matter of fact.

  • Oliver needed a place to go when he got locked out.
  • Vincent could use $12/hour to watch him.

And let’s be honest. When it comes to becoming a spiritual mentor to a kid in your life… sometimes it starts off matter of fact.

And this is what I know from 20 years of working with middle and high school students. Sometimes, that little sliver of opportunity is all Jesus needs to get something big started.

Video: Vincent Talks to God – 14:21 – 14:39

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Rule #3

Walking with Jesus starts right where you are.

One thing I know from walking with God… a starting point is just that. A starting point. And together, in a relationship, well… things are going to happen.

When you and a mentee start walking together with Jesus… change is going to happen.

We see in the life of Paul a change with his relationship to Timothy. When you read Acts 10-15 you encounter a man on a mission… there’s a cycle to it.

He goes to a city, he preaches in the synagogue until they won’t listen anymore, he preaches out in the agora… the city center, he builds a group of believers, it starts to grow… but eventually he puts his nose in everyone’s business and gets his butt kicked, he escapes in the middle of the night.

He comes to town, he preaches, he starts a church, he gets his teeth kicked in, he leaves to the next town.

This isn’t how you build long-term relationships.

But somehow he becomes more than merely an apostle to Timothy, he becomes his spiritual father.

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2 Timothy 2:1-3 “You then, my son, be strong in the grace that is in Christ Jesus. And the things you have heard me say in the presence of many witnesses entrust to reliable people who will also be qualified to teach others. Join with me in suffering, like a good soldier of Christ Jesus.” 

This is something we also see when you mentor someone. You set out to change them, but they change you more.

Rule #4

To be a mentor you have to allow your mentee to mentor you, too.

Video: Are you praying? – 44:47 – 47:39

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When we look at the relationship between Paul and Timothy one thing is important to point out.

  • Paul didn’t lead Timothy to Jesus.
  • Acts 16 says he was already of disciple of Jesus when Paul got there.
  • Slide 14 2 Timothy 1:3-5 provides the starting point of Timothy’s walk with Jesus: “I thank God, whom I serve, as my ancestors did, with a clear conscience, as night and day I constantly remember you in my prayers. Recalling your tears, I long to see you, so that I may be filled with joy.  I am reminded of your sincere faith, which first lived in your grandmother Lois and in your mother Eunice and, I am persuaded, now lives in you also.”
  • Paul was picking up where mom and grandma left off!

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Rule #5

Mentors don’t supercede the role of parents they validate a parent’s message.

Along the way, Oliver somehow manages to weed out the bad stuff he’s learning from Vincent to appreciate the heart behind what grumpiness.

Oliver watches how Vincent loves his wife, who lives in a nursing home, and he learns to love his mom more because of that influence.

Video: I Love You Mom – 1:27:26 – 1:28:25

Let’s take a slightly more voyeuristic look at Paul and Timothy’s relationship.

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2 Timothy 4:11-13 “Only Luke is with me. Get Mark and bring him with you, because he is helpful to me in my ministry. I sent Tychicus to Ephesus. When you come, bring the cloak that I left with Carpus at Troas, and my scrolls, especially the parchments.”

There’s so much we DON’T know.

  • We don’t know how Paul and John Mark reconciled, we just see that they did.
  • We don’t know if Timothy ever made it.
  • We don’t even know how Paul died, tradition holds that he was beheaded, but that story dates to about 110 AD, 40 years after the fact.

But there are things we DO know.

  • The relationship between Paul and Timothy has been preserved through time because of the work of the Holy Spirit.
  • The record of this relationship was preserved for believers to learn from. Luke, the author of Acts, was present when Paul wrote his letter to Timothy.
  • There are not many New Testament relationships we know so much about…
  • We know the church in Ephesus survived, at least for a while. The Apostle John refers specifically to this church in Revelation 2… 90-105 AD range.

And so are here today, bearing witness to– recognizing the work of Paul the mentor of Timothy.

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Rule #6

Mentors aren’t often recognized for their work, but when they are it is awesome.

Video: Presented for Sainthood – 1:29:52 – 1:28:25


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Strive to live like Jesus — to be Paul— you need a Timothy in your life.

  • Paul was deeply flawed
    • He lead a rebellion AGAINST followers of Jesus, it literally took Jesus blinding Paul to get him to give his life to Jesus at all! (You’re doing better than that, already!)
    • He failed at his first recorded attempt to mentor a young leader… John Mark…  in Acts 13:13, Paul and Barnabas ended a long relationship over John Mark in Acts 15:36-41.
    • Paul was fiercely self-sufficient… he only reluctantly received help from the churches he helped start.
    • Paul’s work was his family… he either never married or he neglected his family for the sake of missionary efforts.
  • But Paul sacrificed his way for “The Way” or what we call today, living as a follower of Jesus.
    • As a Christ follower he lead rebellion against Rome that cost him his life but toppled the Roman Empire two centuries later.
    • Rome brought peace forcefully. (Pax Romani… sarcastic way of saying “We bring peace with an army!”)
    • Paul’s strategy was an insurrection of the heart… the more Christians sacrificed, the more powerful and attractive the message became.
  • If we want to see how we can live out a day-to-day life with Jesus, we can look at the day-to-day life of Paul.
    • Paul was deeply flawed, just like us. Yet he chose to be faithful to the God who met him on the road, smacked him upside the head, and set him on a better course.
    • Jesus’ way is to use deeply flawed people to point others to a completely flawless God.
    • And the more we sacrifice what we want, for what Jesus wants in our life, the more we’ll be able to stand back and marvel at what Jesus can do through us.

Take away #1

We can look to Paul as an example of how to live like Jesus wants us to live

And the next takeaway?

Video: The Assignment – 1:06:09 – 1:07:01

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Takeaway #2

Identify the everyday saints in your life







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