“Safety First” has become almost a mantra in our litigious society. Doesn’t it seem like every TV or radio ad ends with a litany of disclaimers, meant to protect the maker of the product from legal action, should anyone have a bad experience? It seems like every message coming at us urges us to exercise caution. Wear your seatbelt, wear a helmet, lock the door, don’t give your personal information out on social media. By the way, all of those are very good cautions. But playing it safe is no virtue when it comes to living out our lives for the Lord. This morning, we’ll be looking at three examples of people taking sanctified risks, and being blessed for it.

I. Courage to defy the odds

(Jonathan & his armor bearer vs. 20 Philistine soldiers)

The first of our three examples this morning is found in 1 Samuel chapter 14. This encounter takes place during the early years of the reign of King Saul. He and his son Jonathan, leading the Israeli army, have been facing off against the Philistines, who were a formidable enemy. Saul has already made several grievous errors in judgment, and at this point, Jonathan begins to act, not a in rebellious way, but nevertheless somewhat independently. And we will see that his faith, which far exceeded that of his father’s, led to courage; courage to action, and action to triumph.

1 Samuel 14:1, 3, 6-15

One day Jonathan son of Saul said to the young man bearing his armor, “Come, let’s go over to the Philistine outpost on the other side.” But he did not tell his father… No one was aware that Jonathan had left… Jonathan said to his young armor-bearer, “Come, let’s go over to the outpost of those uncircumcised fellows. Perhaps the Lord will act in our behalf. Nothing can hinder the Lord from saving, whether by many or by few.”

“Do all that you have in mind,” his armor-bearer said. “Go ahead; I am with you heart and soul.” Jonathan said, “Come, then; we will cross over toward the men and let them see us. If they say to us, ‘Wait there until we come to you,’ we will stay where we are and not go up to them. But if they say, ‘Come up to us,’ we will climb up, because that will be our sign that the Lord has given them into our hands.” So both of them showed themselves to the Philistine outpost.

“Look!” said the Philistines. “The Hebrews are crawling out of the holes they were hiding in.” The men of the outpost shouted to Jonathan and his armor-bearer, “Come up to us and we’ll teach you a lesson.” So Jonathan said to his armor-bearer, “Climb up after me; the Lord has given them into the hand of Israel.” Jonathan climbed up, using his hands and feet, with his armor-bearer right behind him. The Philistines fell before Jonathan, and his armor-bearer followed and killed behind him. In that first attack Jonathan and his armor-bearer killed some twenty men in an area of about half an acre. Then panic struck the whole army – those in the camp and field, and those in the outposts and raiding parties – and the ground shook. It was a panic sent by God.

Later in the passage we find out that the panic was so great, that Saul and the rest of the Israeli army saw the Philistine soldiers all running for dear life. The Israelis pursued and defeated them. God gave victory and deliverance to Israel that day over the much larger Philistine army. And it was just two men with courage and faith that became the catalyst for this triumph. Jonathan’s words echo down through the corridors of time: “Nothing can hinder the Lord from saving, whether by many or by few”. Jonathan’s complete trust in the power of God allowed him to throw caution to the wind and take decisive action. Think of all the people that benefited from that one courageous act!

Jonathan and David were the best of friends, but Jonathan isn’t known among Bible readers only because of that friendship. He was a faith-filled, courageous man, and a valiant warrior in his own right. He is remembered with admiration and with honor. How do you want to be remembered?

II. Courage to defy the majority

(Joshua & Caleb vs. the 10 spies & the hostile Israeli mob)

Our second example is found in Numbers chapters 13 and 14 (which Jerry will be covering again in Parasha Sh’lach next Shabbat, so I am hoping that we’ll all take this lesson to heart). Adonai commanded Moses to send twelve men, a leading man from each of the tribes, to spy out the land of Canaan. They embarked on what would be a 40-day exploratory mission.

The spies returned at the appointed time, and just as God had promised, it was a lovely, spacious and fruitful land; truly eretz zavat chalav u’d’vash – “a land flowing with milk and honey”. They brought back from Eshcol a branch with a single cluster of grapes so huge that it took two men to carry it on a pole between them! They also brought figs and pomegranates. It was a wonderful land the Lord reserved for us! That was the good news.

The bad news, according to ten out of the twelve spies, was that this was ‘mission impossible’. They said, “The people there are much bigger than us, much stronger than us, more numerous than us; their cities are enormous and well-fortified, and as if all that wasn’t bad enough, we saw the descendants of the Nephilim – the giants there!” The ten spies were saying, in essence, “We don’t stand a chance!” And by strictly human reasoning, they were right. But they had forgotten something very important. Adonai had already promised to give us victory over the inhabitants of the land. So, were we going to take God at His word or not?

And this is where our second example of courage comes in. Only two out of the twelve spies, Joshua and Caleb, were willing to trust Adonai for the outcome. They urged the people to proceed on mission, trusting that God would keep His promise. But theirs was the minority report. The other ten spies painted a picture so bleak that they easily convinced our people to abandon the mission, and return to Egypt.

Here is how it played out:

Numbers 14:2-10 (excerpted)

All the Israelis grumbled against Moses and Aaron, and the whole assembly said to them, “If only we had died in Egypt! Or in this desert! Why is the Lord bringing us to this land only to let us fall by the sword? Our wives and children will be taken as plunder…” And they said to each other, “We should choose a leader and go back to Egypt.”

Then Moses and Aaron fell face-down in front of the whole assembly gathered there. Joshua son of Nun and Caleb son of Jephunneh, who were among those who had explored the land, tore their clothes and said… “The land we passed through and explored is exceedingly good. If the Lord is pleased with us, He will lead us into that land, a land flowing with milk and honey, and will give it to us. Only do not rebel against the Lord. And do not be afraid of the people of the land, because we will swallow them up. Their protection is gone, but the Lord is with us. Do not be afraid of them.” But the whole assembly talked about stoning them…

This is, unfortunately, an all-too-familiar pattern. Human beings are sinful and fearful, and more likely to follow the crowd than to take a principled stand. Moses and Aaron and Joshua and Caleb fully understood the gravity of this sin. It was a repudiation of God’s character and His promises. Joshua and Caleb implored the Israelis to repent – not exactly the safest course of action. Predictably, the people refused to listen, and even threatened to kill them!

I’m not going to say much more about this, because I don’t want to completely steal Jerry’s thunder. But there is a very good reason why even little Sunday School kids know the names Joshua and Caleb, and why nobody remembers the names of the other ten spies, though their names are listed in the account. It’s because Joshua and Caleb had the courage to defy the majority that was intent on evil, and to stand up for what was right. They are remembered with distinction and honor. How do you want to be remembered?

III. Courage to defy convention

(A ‘sinful’ woman enters a Pharisee’s home and anoints Yeshua’s feet)

Our third and last of today’s three examples of courage is found in Luke 7, and we’ll spend a little more time here. This encounter includes a wealthy Pharisee named Simon, and a local ‘woman of ill repute’. Talk about two people on opposite ends of the First Century Israeli social spectrum – this is it! And in the midst of them, Messiah Yeshua Himself.

Luke 7:36-50

Now one of the Pharisees was requesting Him to dine with him, and He entered the Pharisee’s house and reclined at the table.

It’s understandable why one of the Pharisees, whose name we later learn is Simon, would invite Yeshua to his home for a meal. After all, this young carpenter-turned-rabbi had only recently begun His public ministry of teaching and healing, and already had cured a leper, restored a paralyzed man, cast out demons, healed a centurion’s servant who was about to die, and raised a man from the dead. Word on the street was that this rabbi had the power of God at work in Him, and yet was gentle and kind-hearted. Wouldn’t you be curious to meet someone like that?

What do we know about Pharisees? We know they were the pious, ultra-religious sect of Judaism. They were the machers – the big shots, fancying themselves the “gatekeepers” of Judaism. People held them in a mixture of reverence for their piety, and yet disdain because they could be harsh, hypocritical and egotistical.

Many Pharisees were well-to-do, and it’s likely that Simon was among them. He hosts a meal at his home, and invites Yeshua to come. To have a rabbi come into your home was considered a high honor in ancient Israel. Yeshua accepts the invitation, enters the home, and reclines at the table with the others.

And there was a woman in the city who was a sinner; and when she learned that He was reclining at the table in the Pharisee’s house, she brought an alabaster vial of perfume, and standing behind Him at His feet, weeping, she began to wet His feet with her tears, and kept wiping them with the hair of her head, and kissing His feet and anointing them with the perfume.

We aren’t told the name of this woman, but Luke says she was regarded as a sinful person – in Greek, hamartolos. Most likely it was sin of a sexual nature. Probably she was a prostitute, though there is a Greek word for that, and it isn’t used here. ‘Sinner’ may have been a gentler expression.

But here’s the salient point: she heard Yeshua was in town, and dining at the home of this Pharisee, and she wasted no time going there to see Him. Consider the level of her determination: a woman with a reputation, walking into a Pharisee’s home. She knew who she was, and she knew they knew who she was, but she wouldn’t be deterred. She knowingly walked into an embarrassing situation out of a deep desire to see the One about whom she had heard so much. This Rabbi isn’t like the others. This One doesn’t point fingers. This One welcomes sinful people to come to Him, and in the process, they leave their sin behind! So what’s a little embarrassment in exchange for that kind of opportunity? She threw caution to the wind. And that is precisely the kind of courage and determination that pleases God.

And, I hasten to add, she didn’t show up empty-handed. She brought with her an alabaster vial of ointment – the Greek word for it is muron, from which we get the word myhrr. And at one point she is overcome with emotion and begins weeping.

Now Yeshua and Simon the Pharisee (and presumably others) wouldn’t have just sat there, eating. No doubt they discussed the Torah and the Prophets and the things of God. Perhaps as Yeshua spoke about the Kingdom, explaining God’s ways, and God’s mercy, the woman broke down. Is it possible that mercy was something with which she had very little personal experience? The Greek construction of this sentence suggests she was weeping very deeply, perhaps uncontrollably.

Luke says, she began to wet His feet with her tears, and kept wiping them with the hair of her head, and kissing His feet and anointing them with the perfume. Those were not wasted tears. But perhaps she’s embarrassed that her tears have fallen on Him. And so she kneels down and uses her hair to wipe His feet. What we are seeing is an act of great humility and faith. Assuming this is the first time this woman has seen Messiah Yeshua, she can only trust that He is as kind and merciful as she has heard, and that she will not be rebuked by Him.

But in contrast to this woman’s adoration, Yeshua is disdained by His host. Now when the Pharisee who had invited Him saw this, he said to himself, “If this man were a prophet He would know who and what sort of person this woman is who is touching Him, that she is a sinner.”

We can glean from this that on account of Yeshua’s many miracles, people were already heralding Him as a prophet. And that He was… though much, much more. But the Pharisee is indignant. He thinks to himself “Is this guy clueless? Doesn’t he know who and what this woman is that he’s letting touch him? Some prophet!”

How did Luke, who wrote this, know what Simon the Pharisee had been thinking? Do you remember that in the opening words of his Gospel, Luke claims to have thoroughly investigated all the stories that had been handed down to them. So, there are two possibilities here. Either Yeshua revealed that fact to the disciples who were there with Him that day, and they confirmed it, or else – and this would be very cool – Simon the Pharisee eventually became a disciple himself, and admitted to Luke what he had been thinking that day.

But for the moment, the Pharisee has only contempt in his heart; contempt for the woman for her sinful lifestyle, and contempt for Yeshua, whom he presumed not to know who this woman was. And now the Messiah addresses His host.

Yeshua answered him, “Simon, I have something to say to you.” And he replied, “Say it, Teacher.” “A moneylender had two debtors; one owed five hundred denarii, and the other fifty. When they were unable to repay, he graciously forgave them both. So which of them will love him more?” Simon answered and said, “I suppose the one whom he forgave more.” And He said to him, “You have judged correctly.” Turning toward the woman, He said to Simon, “Do you see this woman? I entered your house; you gave Me no water for My feet, but she has wet My feet with her tears and wiped them with her hair. You gave Me no kiss; but she, since the time I came in, has not ceased to kiss My feet. You did not anoint My head with oil, but she anointed My feet with perfume. For this reason I say to you, her sins, which are many, have been forgiven, for she loved much; but he who is forgiven little loves little.”

Yeshua didn’t attempt to whitewash the woman’s sin. Her sins, He acknowledges, are many. By contrast, Shimon the Pharisee has lived a life of religious devotion. Yet according to Yeshua, the greater sin between the Pharisee and the prostitute was the absence of love. Simon reckoned himself righteous, and not in need of forgiveness. As a result, he lacked mercy, and completely missed the significance of the One sitting right there at his table.

Hospitality in the ancient world, and especially in the Ancient Near East, was a sacred responsibility. Even today, to be invited to a Jewish home and not to be offered something to eat and drink is a sign of disrespect. In ancient Israel, when you invited someone to your home, it was customary to provide water for your guest to wash their dusty, tired feet. It was customary to welcome them into your home with a kiss. If you had sufficient means it was customary to anoint their head with a little oil. Simon had done none of those things for Messiah. Inviting Him to his home seems to have been an act of condescension, as though he felt he was doing Yeshua a favor, and so he had dispensed with the usual politeness.

You see, it wasn’t just Simon’s lack of love compared to the woman generally that earned him the rebuke. It was his lack of love for Yeshua – this is all about Him. Don’t miss that. The extent to which you either love Him and give Him your very best, or treat Him with indifference, will be the determining factor in the disposition of how you spend eternity!

Messiah tells Simon the Pharisee that the woman’s many sins, in view of her love for and faith in Him, are forgiven. And now Yeshua turns to the woman directly and declares it. Then He said to her, “Your sins have been forgiven.” Those who were reclining at the table with Him began to say to themselves, “Who is this man who even forgives sins?” And He said to the woman, “Your faith has saved you; go in peace.”

The forgiven sinner comes away from this encounter joyful and with a clean slate and a fresh start. The self-righteous come away from this encounter critical and even more hard-hearted. And that is the nature of things with Messiah. He is the ‘Stone of stumbling’ and the ‘Rock of offense’ to the self-satisfied. But to the humble, He is the Fountain of Living Water. Yeshua the Messiah is the most pivotal individual in all of human history. How we approach Him is the single most important decision each one of us will make in this life.

So we’ve seen in Jonathan and his armor-bearer the courage to defy the odds; in Joshua and Caleb the courage to defy the majority; and in this unnamed but blessed woman the courage to defy convention. Each situation was fraught with danger.

So, what are we to learn from these three examples? Well, first of all, there is no reward in Heaven, and no lasting memorial for those who play it safe when it comes to representing God in this world. By contrast, those who throw caution to the wind, risking ridicule and even worse for Messiah Yeshua are remembered with honor.


You aren’t being asked to pick up a sword and fight and put your life on the line. Is it too much to ask that you pick up your Bible and go out and do some good old-fashioned evangelism? Not one person named in the “Hall of Faith” in Hebrews chapter 11 got there because they played it safe. Every one of these great men and women took risks. How do you want your epitaph to read? “He was a nice guy”? Can I tell you something? Multiplied billions of ‘nice guys’ have lived and died and are altogether forgotten, because they lived their entire lives playing it safe, never risking anything for Yeshua, and never so much as making a dent in the enemy’s agenda. If you want to honor God and Messiah, then put safety second. God willing, we’ll continue this theme next Shabbat.