Meet the man who never stopped plotting, Abdullah ibn Ubayy ibn Salul.

For the entire duration of the Prophet's ﷺ time in Madinah, this man was like a poison coursing through the community's bloodstream.

He wasn't an enemy from the outside that you could face directly; he was a cancer from within, constantly undermining, constantly plotting, constantly working to make the Prophet's ﷺ mission fail.

Picture the exhaustion of dealing with someone who never, ever takes a break from trying to hurt you.

While the Prophet ﷺ was building a society, Abdullah was trying to crumble it.

While the Prophet ﷺ was uniting hearts, Abdullah was sowing division.

While the Prophet ﷺ was establishing justice, Abdullah was collaborating with external enemies.

For years.

Without pause.

Without mercy.

Then Abdullah ibn Ubayy died.

And here's where the Prophet's ﷺ beautiful, overwhelming mercy created a crisis that nobody saw coming.

His son, a righteous companion who was mortified by his father's actions, came to the Prophet ﷺ with a heartbreaking request.

"Ya Rasulallah, could you please pray the funeral prayer for my father?

And could you... could you wrap him in your own garment?"

Imagine the son's desperation.

He knew exactly who his father was, exactly what he had done.

He was looking for any gesture, any sign of mercy that might somehow provide his father with a chance for divine forgiveness.

The Prophet ﷺ, whose mercy was as vast as an ocean, couldn't bear to refuse a grieving son.

He not only agreed to pray the funeral prayer—he took off his garment, the same gesture he had only done for his beloved uncle Hamza (RA), and wrapped Abdullah ibn Ubayy in it.

Can you imagine the emotional weight of that moment?

The same honor for the leader of the martyrs was now bestowed upon the man who had spent years trying to destroy everything the Prophet ﷺ held dear.

But as the Prophet ﷺ moved toward the prayer area to lead the funeral prayer, Umar (RA) stepped in front of him.

Imagine the strength that took.

Umar (RA) knew that every hypocrite in Madinah would be watching this moment, calculating what it meant.

"Ya Rasulallah," he said, effectively blocking the Prophet's ﷺ path, "this will send the wrong message."

The unspoken logic was devastating in its clarity:

If the Prophet's ﷺ mercy extends even to the arch-hypocrite, if even Abdullah ibn Ubayy gets a funeral prayer led by the Messenger ﷺ of Allah himself, then what deterrent exists for others who might be tempted toward hypocrisy?

The revelation that followed was both gentle and firm.

Allah didn't rebuke the Prophet ﷺ for his mercy, for mercy was the very quality that made him beloved.

Instead, the verses made clear that there are times when even divine qualities need boundaries.

The Quran established that prayers should not be offered for those who die in a state of confirmed hypocrisy, not out of cruelty, but as a deterrent.

A way of protecting the community from the message that destructive behavior has no consequences.

This story addresses one of our most pressing modern dilemmas.

We've all been there: the family member who constantly takes advantage of our generosity, the friend who always creates drama and then expects unlimited forgiveness, the colleague who mistakes kindness for weakness.

Our hearts want to keep giving chances, but wisdom sometimes demands boundaries.

What's remarkable about Umar (RA) in this story is his willingness to be seen as the harsh one, the unforgiving one, to protect something larger than any individual relationship.

He understood that sometimes mercy to one person can become cruelty to an entire community.

Perhaps the most profound lesson here is that even the Prophet ﷺ, with his perfect character and divine guidance, needed counsel.

It reminds us that struggling with these boundaries is part of the human condition and a beautiful heart.