Jesus, The Wailing Savior

Most of us are familiar with the moment when Jesus weeps at Lazarus’s tomb, but I was recently caught off guard by a moment of deep grief in the Easter story—one embedded in the triumphal entry itself.  

As part of my journey through Lent, I’ve been reading 40 Days of Decrease by Alicia Britt Chole, and in chapter 16, she highlights this moment in the Easter story. Although I had read it before, it struck me deeply, and I haven’t been able to stop thinking about it since. 

As Jesus rode into Jerusalem on what we now call Palm Sunday, amid the praises and palm branches, Luke’s Gospel tells us that Jesus wailed over the city (Luke 19:41-44). The Greek word used—kaleo—is not a quiet tear or a soft sigh. It’s the deep, guttural cry of lament.Think ugly, loud, and obnoxious sorrow. The kind of wailing you’d expect from a father who has just lost a child.

I'm simultaneously repulsed and drawn to this image of Jesus grieving in such a raw way.

I think it has to do with my resistance to engage in my own unrestrained sorrow.

In a recent story work session I was asked this surprising question,
"Do you know the sound of your wail?"  

I almost laughed. What do you mean? I thought. I don’t wail. I swallow my tears. I make my crying as quiet as possible. And if I ever do wail, it’s only when I am confident no one can hear me.  

My storywork facilitator leaned in, gently pressing against my resistance:  

“Tori, you cannot only connect to the parts of you that are joyful, confident, and secure. If you want to live fully alive, you must also learn to hear and honor the sound of your wail. To grieve is to name value. Both of these elements of your humanity must be honored and embraced.” 

And isn't this exactly what we see in Jesus? Fully holy, fully in unity with the Father-and yet, he weeps. 

No silent cry for Jesus — he screams his sorrow surrounded by a crowd. He wails over the peace and Jerusalem refuses. He names the grief of what was lost.  

We often feel pressure to rush to Resurrection Sunday, to stay in the joy, to avoid the sorrow. But Jesus invites us to all of it—the rejoicing and the weeping.

Turns out, messy is not a sin.

I once heard someone say they know they have the presence of the Holy Spirit in them because they know when they grieve the Holy Spirit (Ephesians 4:30). 

When our spirit is moved to lament, it’s always an invitation back to hope, repentance, and redemption through the process of grief. Our sorrow named a hope we are desperate to see fulfilled.  

So I ask you: Where is God weeping over your life?

What has been stolen, broken, or lost that grieves His heart?  

This Easter, don’t be afraid to bring your loud, obnoxious, unrestrained grief to God. Your weeping is not a cry of defeat—it’s a war cry that names value and leads to back to your savior who holds the victory.  
 

Praying for you as you journey with Jesus this Holy Week, 

Tori
Freedom Coach & Director of Marketing & Strategy