Ben Fleming: The Luckiest, Matthew 5:1-12

April 19, 2026 00:25:57
Ben Fleming: The Luckiest, Matthew 5:1-12
Westside Church
Ben Fleming: The Luckiest, Matthew 5:1-12

Apr 19 2026 | 00:25:57

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Show Notes

Westside One: On the Mount Week 2 | The Beatitudes reveal an upside-down kingdom where Jesus made statements like “Blessed are the poor in spirit…” (v. 3) and “Blessed are those who mourn…” (v. 4). Jesus did not mean that these people earned blessings by being sad or broken – instead he revealed how the Kingdom of God is available to those who are in broken places.

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Episode Transcript

[00:00:00] You're listening to a live recording from Westside Church in Bend, Oregon. Thanks for joining us. [00:00:07] Good morning, everybody. I'm Ben Fleming, one of the senior pastors here, and we're in part two of this series, Sermon on the Mount. And I love how he phrases it. It's this manual for Christian discipleship or this kind of guidebook for Christian discipleship. And it's one of these things that I hope we are willing to carry with us in every single thing as we get into the Scriptures today and we talk about the Beatitudes, really, the entire Sermon on the Mount, it's a masterpiece of teaching by Jesus that I hope is just in everything. How we think about our relationships and our friendships, how we think about our future, how we think about our past, how we think about politics. Every single bit of how we process how we should exist in this life should be filtered through this Sermon on the Mount. The Beatitudes, really, it might be helpful to think about it this way, is that the Sermon on the Mount for us should be like protein in every single food that you can find in Costco. [00:00:59] Okay. Have you noticed this? That every corner you walk around, like, oh, the snacks. Oh, this has 10 grams of protein in. This has 30 grams. Oh, the flour's amazing. Three grams of protein in these flours. [00:01:13] Excuse me. The flowers have prebiotics in them and probiotics. [00:01:18] Not really. I bought my favorite sunflower seeds the other day, and they were like, we have six grams of protein. And I looked at it closer, I was like, I gotta eat this whole bag, which is like 10 times the salt intake. I should have, you know, in just a couple of hours. Sunflower seeds. I don't need you to be protein filled. I just need you to be salty and something for me to do while I coach softball. Like, that's all I really need. [00:01:42] So don't try too hard. Sunflower seeds. Pepsi's got pre. Okay, let's move on. Here we go. [00:01:47] But this should be in every single thing that we do. We should take this into consideration. The temperature that Jesus has, the tenor that he has inside of this sermon. So here it is. Matthew, chapter 5, verse 1. Many of you are going to be familiar with this section of scripture, and what I've discovered is that all of us say blessed when we read this, and we don't say blessed in any other context in our whole lives. And I talked to Dr. Brandt and I said, is it blessed? And he was like, there's no real reason for it to be blessed. I'm Going to say blessed today and it might throw you off. [00:02:21] Careful. Matthew 5, verse 1. Now, when Jesus saw the crowds, he went up on a mountainside and he sat down. The disciples came to him and he began to teach them. He said, blessed are the poor in spirit, for theirs is the kingdom of heaven. [00:02:33] Blessed are those who mourn, for they will be comforted. Blessed are the meek, for they will inherit the earth. And blessed are those who hunger and thirst for righteousness, for they will be filled. Blessed are the merciful, for they will be shown mercy. [00:02:46] Blessed are the pure in heart, for they will see God. Blessed are the peacemakers, for they will be called children of God. And blessed are those who are persecuted because of righteousness, for theirs is the kingdom of heaven. [00:02:59] Blessed are you when people insult you, persecute you, and falsely say all kinds of evil against you because of me. Rejoice and be glad, because great is your reward in heaven. For in the same way they persecuted the prophets who were before you. [00:03:13] This is the word of the Lord, Father God. We pray that we would. We'd be changed, that our hearts would be filtered. Everything that we see and think through this life and what it means to follow you. I pray that it would move through these things, that we would understand what blessing truly is, and we would live in such a way. In Jesus name. [00:03:32] Amen. [00:03:34] Amen. Well, happy baseball season, everybody. As if it ever stopped. For me, I think if you have a kid or a grandkid or a friend or whatever that is anywhere from like 5 to 12 and they're playing baseball, I think they played yesterday. Beautiful day, pictures, the whole different crazy kind of thing. [00:03:52] And if you don't know already, which means this is your first Sunday here. I love baseball. [00:03:58] Baseball's my favorite thing. [00:04:00] You know, family and all that stuff. And baseball after that, and. [00:04:05] And I just love it. I love the game. And I also understand that when I use these metaphors and these illustrations, that I'm probably talking to a crowd that does not care about baseball nearly as much as I do, if at all. I know games can be long. I know watching Little League games in the snow is not what people want to do. And I understand. I acknowledge all these things. But when I talk about baseball, for me, baseball was this thing as a kid that. That wasn't just fun, but it was something that actually introduced me to the world that I lived in. And that was because my grandpa Doug, my mom's dad, recorded on VHS tapes this baseball documentary by a documentarian named Ken Burns that aired on pbs. [00:04:46] Ken Burns might be the most famous documentary guy in American history, right. He's done the Civil War was his huge documentary. And I think he just did the American Revolution, he's done Vietnam, he's done all kinds of things. [00:04:59] And my grandpa sent these on VHS tape. He recorded them in Beaverton and mailed them to us. And I can still see his handwriting on the white label of the VHS tape where it says baseball one and two. You know, our innings one and two, because there were nine parts for nine innings. [00:05:15] And he sent these to us. And you know, we didn't have cable or anything like that. We had one of those 12 inch TVs that had a cassette embedded into the bottom of the screen. Right. So you, you put in the VHS tape. Yeah, I'm preaching to some of you today. [00:05:30] And I think the dog ate Innings one and two. So I didn't get to watch those till like college. And I got the DVDs. [00:05:37] But I would watch these documentaries and I would watch Oliver the Musical and I would watch the Star wars trilogy just kind of on loop because that was all we had. [00:05:48] And I remember watching these documentaries and it wasn't really about purely about baseball, right. But it was about American history. And so I was introduced to the world around me. I was introduced to the Civil Rights movement through the story of Jackie Robinson. And I was introduced to this idea of unions and labors through. And labor through the story of the lawyer Marvin Miller and Curt Flood who played for the St. Louis Cardinals. And I was introduced to the 60s and the 70s. And I was introduced to Americans movements from east to farther out west through this game. And so it was more than just baseball for me. It was about the story of the world that I live in. And so first of all, when I talk about baseball, I believe that everyone has an experience like I've had with baseball. Baseball through the arts or a game or a book or a story or a hobby. It introduced you to the world around you. And baseball for me taught me a lot of these lessons, even about grief and suffering and death and that specific story. I remember being particularly impacted by a man named Lou Gehrig who played for the New York Yankees. [00:06:55] And he's one of the greatest baseball players of all time. He played with Babe Ruth. He hit right behind him in the four slot, Babe Ruth hitting the three. And they kind of had this healthy competition together, didn't like each other for a long time. Lou Gehrig famously was called the Iron Horse, and He played in 2,130 consecutive games in baseball before Cal Ripken Jr. Broke his record in the 90s. He held the record for that. But what happened to this iron horse man, this toughest, one of the greatest players to ever live as he contracted this disease that we know of course is Lou Gehrig's disease at als. And so he was playing and then all of a sudden, very quickly, he declined. He had to stop. And on July 4, 1939, they called it Lou Gehrig Appreciation Day at Yankee Stadium. And Lou Gehrig addressed this crowd of adoring fans with this speech in which he says, fans, for the past two weeks you've been reading about a bad break that I got, and yet today I consider myself the luckiest man on the face of the earth. I've been in ballparks for 17 years and never received anything but kindness and encouragement from you fans. When you look around, wouldn't you consider it a privilege to associate yourself with such a fine looking men as are standing in uniform in this ballpark today? Sure, I am lucky. [00:08:10] And when you have a father and mother who work all their lives so that you can have an education and build your body, it's a blessing. [00:08:15] And when you have a wife who's been a tower of strength and shown more courage than you dreamed existed, that's the finest I know. [00:08:22] And so I close in saying that I may have been given a bad break, but I have an awful lot to live for. Thank you. [00:08:31] And I remember as a kid hearing this word lucky in a way that I had never heard lucky before. [00:08:38] Lucky is winning the 5050 raffle. And lucky is when you bet on red, it lands on red. Lucky is getting the right card on the river in poker. Lucky is not what Lou Gehrig is talking about. [00:08:51] This is the opposite of luck. [00:08:53] And the reason that this story came to mind is I was reading through the Divine Conspiracy that's written by Dallas Willard, which is kind of this masterpiece modern Christian book about the Sermon on the Mount, about the Beatitudes. And I was also heard this story about a man named Eugene Peterson, who's one of the greatest writers in Christian history, wrote the message translation. [00:09:15] And in this book by Willard, he says a better word for blessed is lucky. [00:09:22] And Eugene Peterson tells this story about how when he was writing the message translation, he wanted to change blessed to lucky. [00:09:29] And his publishers didn't like it. They thought it sounded too random and that it would offend Christians, and so they left it out. [00:09:35] But both of these men, titans of writing theology, thought Lucky would be a better word than blood blessed. [00:09:43] And come to find out, it's because they felt like the word blessed had been a little bit commandeered by the modern version of faith, that when we say blessed, we actually mean now look at all the hard work I've put in and all the things I've done, all the deposits that I've made. And now my withdrawal from this kingdom of God is actually the blessing that comes from it. And what both writers wanted people to understand. As he says, blessed are the poor in spirit, blessed are those who mourn, blessed are those who, who are meek. That word blessed can kind of feel a bit distant from us. [00:10:13] And Willard says the Beatitudes are proclamations of who is well off when the kingdom of God is available. They're not instructions and they're not indications of who's achieved the most. And they're not just announcements. He's actually talking about who are the lucky ones. [00:10:28] And the reason that he's. He uses, that he wants to use the word lucky is he's trying to translate this Greek word which means something like deeply well off or in a truly good position. And he's also trying to help them understand and shake us out of this thing, that this lucky feeling should create that emotion that we have when we shockingly find ourselves in the right position, when we were sure we were in the wrong one the entire time. [00:10:52] That blessed in our current day and age kind of creates this idea of, yes, well, I am blessed and lucky creates a little bit more of what you're seeing when it comes to watching Wheel of Fortune late at night. And it's, You heard these people, people on game shows are fantastic. I think they pick them up. But, you know, the price is right people are the best. Especially, you know, And, you know, there's a big difference between that response and, well, you know, I count myself as blessed. [00:11:29] And both authors are saying this thing. These people that would have been under the sound of Jesus's voice would have been in the context of hearing that if their lives were difficult, it was because of sin that they had committed or sins that their ancestors had committed. And whatever difficulty they were experiencing in life was actually simply just their fault. [00:11:47] And they would be considered the lowest of the lower, certainly lowers lower lower than those who actually had more than them. This was actually a definitive measuring stick for how well they were living life. And so Jesus comes in and presents this upside down kingdom that would have been such a relief to these people, listening to them, to him, dragging themselves in and going, I wonder if he can teach us something that we can take a hold of and then we can be better people and so that we can then live a life that we're hoping to live. But Jesus is saying, you're lucky, you're blessed. You are so fortunate because the kingdom of God has found you here and now, despite whatever you have done or whatever kind of life you have lived to this point. [00:12:28] And for these people, it doesn't create this. Oh, yes, well, thank you. It's. Oh, we're in. [00:12:36] We. Can you believe this? [00:12:40] How could these people be the lucky ones? And Jesus says that they are. [00:12:45] And so these aren't a list of virtues to achieve, right? We have to be careful with this. It's not a list where, in descending order, as you go down these, there's more holiness and more glory contained at the bottom there, this declaration there. These are the people who are in a good place because the kingdom of God is now open to them. Or as we might say it, these are people who, in light of the kingdom, have found themselves to be the luckiest. And so Jesus names these groups, right? He names the poor in spirit, he names the grieving, he names the overlooked, and he names the hungry. Why them? Because they are people that are confident and they know that they have a great need. [00:13:24] They are looking for something outside of themselves that can actually fill their soul because they are confident that they are not doing it on their own. [00:13:33] And Jesus is speaking to this thing that a lot of us can fall for in our own lives. That if we are taken care of and that if we are comfortable and that we are self sufficient, oftentimes whether we say it out loud or not, we can begin to think of ourselves as our own God and we can begin to worship our own willpower. [00:13:50] And Jesus says that is a difficult place to see the kingdom. From Dallas Willard said, Jesus isn't saying everyone who's poor is blessed. He's saying that even the poor may now live in the kingdom. [00:14:02] It's not romanticizing hardship I want you to understand, but it's about understanding, access. [00:14:09] Because we've been trained to believe that life comes from and life well lived comes from achievement and comfort and control. [00:14:18] Hello. Somebody elbow someone next to you? Just kidding. Don't do that. [00:14:24] Recognition. [00:14:25] We believe that this is evidence of a life well lived. If we have found these four things, achievement, comfort, control, and recognition. But Jesus is saying in this upside down kingdom, teaching that life comes from somewhere else. He says, the first shall be last and the last shall Be first. Cause the kingdom of God rearranges where life actually comes from. And so now the poor in spirit are lucky because they're open. The mourners are lucky because they're not numb. The meek are lucky because they're free from the illusion of power. And the hungry are lucky because they are still seeking what actually matters. [00:15:03] People who have suffered and experienced these things again, like Lou Gehrig, who finds himself at this difficult point in life, not talking about how great his career was, but instead all of a sudden sharing his perspective on the people in the world around him. Because of his suffering, he can see things that not many of us can see. [00:15:23] I found this in two of the greatest sacraments of church. I've been a pastor for 17 years. [00:15:31] I keep forgetting. [00:15:32] And I'm noticing that I'm getting a little bit older because not only can I not remember how long it's been, but I don't care. [00:15:41] Have you noticed this? [00:15:44] What I've got, I've done. I've done over 110 weddings now, which is really, really fun and amazing. Weddings are a blast. They're also, I can tell. And I am in a very privileged position because I get to kind of swoop in. [00:15:59] They're very stressful for people. Have you noticed this? [00:16:03] So many people to keep happy at a wedding. [00:16:05] And you can figure it out in an instant. The pastor shows up and people notice that you're the pastor. And then all of a sudden I get the wedding coordinator, I get the groom, I get moms and dads, I get the whatever. And I can feel the temperature almost immediately of how things are going, if they're going well, if they're going poorly. And I always feel for that one person. It's not always the wedding coordinator. There's always somebody trying to just hold this stinking thing together. [00:16:27] And I don't mean by getting everything going on time, but I mean by keeping everybody happy. And then what you notice is that one person, by the time the evening is over, often is not every wedding. I don't believe that it's yours or it's gonna be yours or whatever. All right. [00:16:40] But what you see from that one person at the end of a wedding a lot of times is like, oh my gosh, thank God they're married and gone. [00:16:49] And then there's a lot of like post game discussion about how weddings went. Right. I remember being unmarried, but kind of on the verge of my own wedding. And then you go to a wedding and then you get in the car and Go. Well, let me tell you what st about that wedding that we're not gonna do, you know, and then there's people. It's the drinks and it's the food and it's the timing and how. Wait. How long we waited for the cake. Hurry up and dance, you guys. I'm sleepy. [00:17:18] A lot of these conversations can happen, and weddings are great. [00:17:22] You know what I've actually found, and they're super. They are tremendously wonderful and fulfilling. Seriously, they're awesome. [00:17:28] You know what is maybe the most fulfilling thing I've ever experienced in ministry? It's not teaching in front of thousands of people on Easter, Christmas Eve or whatever. Those are cool. [00:17:38] Memorial services are the greatest things in the whole world. [00:17:44] And it's because nobody wants to be there. [00:17:48] Because. And now that I'm reading through this, I look at it and I go, it's because we're actively walking in the Beatitudes. When we go to a memorial service for somebody that we love, whether it's the most unbelievable tragedy that'll completely rip your heart out or whether it's somebody that's lived this long and full life, we all feel this connection to something isn't quite right. [00:18:09] And I see it, you guys. I've seen it in here. The rich people and the poor people come, the cousins and the husbands and the wives, the closest and the. And we all feel this sense of no matter where we've come from, this sense of something isn't quite right and we're a little desperate and we're sad and we're grieving. [00:18:28] And you watch people as they leave. There's the biggest hugs happen at funerals, the most connection. [00:18:41] And I think it's because we're seeing ourselves in these places. We're seeing ourselves be hungry to be with someone that we've lost. We're feeling meek, we're mourning. [00:18:51] We're poor, no matter how rich we are, because we have this sense and understanding of our own brokenness and things that are missing. [00:19:02] It pulls us into this place that Jesus is calling us into where we can more clearly see the kingdom of God. [00:19:10] And so again, Lou Gehrig says at the end of his strength, he says, I consider myself the luckiest man on the face of the earth. Why? Why? Not because his circumstances are good or his life is going as he had planned. But it was all of a sudden, it was like the blinders could come off and he could see love and relationship and meaning and gift. [00:19:33] And so, in other words, it's like he had discovered in this moment, and we see it in this speech, something that was far deeper than just the overall circumstances that he's facing. [00:19:43] And Jesus is saying something even better than Lou Gehrig and even more profound. He's saying, even when your life looks like loss and people would point at you and say your life has been lost, the kingdom of God is still available to you. [00:19:58] And when the kingdom is available, we have to remember that we haven't been left behind or forgotten, and we're not disqualified. I've come to know that maybe the worst feeling is in all of human history is that feeling of being left behind or outside of the community or lonely. [00:20:15] I got to see this in my son's face. My family and I went to Seattle this last year, and I love taking public transit. I love trains, I love buses. I love. It's like a giant slice of humanity just in a little moving box going through downtown. And we stopped at this one stop, and my son made the mistake of thinking that that was our stop. [00:20:33] And he walked right out that door. [00:20:36] And me and my wife and daughter are standing there going, oh, and the door's closed. [00:20:41] And there's my son face to face with me with a door between us, immediately going from this really confident kid to, what's the worst thing that happened to me? That I would be left behind, That I would be sitting right here, right next to you, but outside of where you are. And luckily, by the way, everyone screamed in the bus, thank God for all the other pastors, no, no, no, don't go anywhere. You know, I opened back up and boy, my son never loved me more than he did in that moment. You know, it's like we had our own little funeral right there. He's like, oh, why don't we do that again? [00:21:18] He loves me now. [00:21:22] Oh, to be left behind. [00:21:24] And you guys, I think faith, I think church, maybe your experiences in past with, maybe it's been here, maybe it's been somewhere else, can so often create this understanding because of how things have gone in our lives or how we're feeling in this moment. It's like we're right next to everybody that's found themselves on the bus. But the door is closed and I can look in, but I am not a part of what they're doing because things have gone wrong for me. I've made mistakes. You have deep regrets. And Jesus, the beauty of this upside down kingdom is saying. He's saying you're actually lucky. You're in a good position and finding yourself in this place because those who are full of self righteousness, believing that they have been blessed because they have pulled all the right triggers and they've said all of the right things, they will so often miss this kingdom. But those of you who are desperate and hungry and poor and thirsty, those who are. Who know that they need a savior. [00:22:17] And so this is why the world's version of what we call a good life, I think, continues to collapse around us. And maybe you've experienced this because it's built on things that can't carry our soul, right? Success. And we can still feel empty, we can experience comfort and we can still feel anxious, we can be recognized and still feel completely unseen. Because those things were never meant to actually be able to carry and hold the weight of your life. [00:22:46] So who are the luckiest people? According to Jesus, it's the luckiest people who are not. Those that have the most because they know they need God. They're willing and humble enough to turn to him in their weakness and discover that he is actually already near. [00:23:05] The luckiest people are those who realize that I don't have to earn my way into this life with Jesus, but instead I can simply receive it. [00:23:17] And so, as we prepare to close our time together today, I just want to encourage you just to close your eyes for a moment and kind of picture this in your mind with me. [00:23:28] Picture Jesus standing on that hillside and looking out at ordinary and overlooked and struggling people. And then find your own self in that crowd. [00:23:44] And then in that moment, I want you to hear Jesus look out on you and say, you are the lucky ones. [00:23:52] You're blessed not because life is easy, but because the kingdom is open to you. [00:24:01] God is near, right here and now. [00:24:06] And this real life is truly available to you right here and right now. [00:24:15] Lord Jesus, we just pray that especially for those who raise their hands, but for all of us in the room, pray that we would be confident that you see beyond the surface. [00:24:29] You see beyond our successes and beyond our failures. [00:24:35] Teach us to stop chasing life in places that simply cannot hold the weight of it. [00:24:42] Lord, I pray that they would know that you're here to give us courage to come to you. [00:24:50] And you're so aware of our need. [00:24:53] So, Lord Jesus, meet us in this moment in grief, in our greatest of hungers and longings and our weaknesses. [00:25:00] And I pray that we would be able to discover that you're already here with us, make us this people that live in your kingdom. [00:25:13] Whether we're rich or poor, whether we're healthy or broken, whether we have clear pictures and visions of the future, or we're so exhausted that we remain right in this moment. [00:25:29] Pray that we would live in your kingdom in spite of all of the things and that we would know by your grace we're actually the luckiest of all. [00:25:38] In Jesus name and everybody said Amen. We're going to take communion here in a moment. If you want those elements brought to you, you can raise your hand right now and somebody will bring those around to.

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