These verses are often seen as a series of 8 “woes”
Perhaps we might consider the 1st “woe” as the overall description of what these men were doing
The next 7 woes are descriptions of their evil actions & attitudes in closing the door to Heaven

I. Shutting The Kingdom Of Heaven V. 13

A. The Fault Of The Jewish Leaders

1. Woe- exclamation of grief
2. These religious leaders shut up the kingdom of heaven to themselves and others

a. Shut up- to obstruct the entrance into
b. Their lives & teachings prevented people from entering Heaven
c. By their lives & teaching, they pointed people to religion, but away from God
d. People that were on the right path to God were redirected away from God
e. NOTE- There is biblical teaching about…

i. God’s sovereignty in drawing people to Himself vs. man’s free will
ii. The fact that people can steer others away from God
iii. These biblical themes are impossible to reconcile, but are to be believed

3. These men were worse than those who rejected God on an individual level
4. These men were guilty of steering people away from God, & all in God’s name
5. These men would be more guilty than those who simply rejected God
6. James 3:1 My brethren, let not many of you become teachers, knowing that we shall receive a stricter judgment

B. We Are To Open The Kingdom Of Heaven Unto Others

1. Turn to Matthew 28:16-20
2. Turn to Matthew 18:1-7

a. We are not to hinder people from coming into the Kingdom of Heaven
b. There is terrible judgment for those who steer people away from God

II. How They Shut The Kingdom Of Heaven

A. They Exploited Vulnerable People To Enrich Themselves V. 14

1. What exactly they were doing is unclear
2. The general understanding is clear:

a. They took people’s property under the guise of serving God
b. In God’s name, they exploited vulnerable people to enrich themselves
c. Widows- not highly esteemed, vulnerable, needy, alone
d. Devoured- consume by eating, forcibly appropriate, to strip one of his goods
e. Pretense- a pretext (alleged reason, pretended cause)

3. Possible ways they did this:
Matthew Henry- …they devoured widows’ houses, either by quartering themselves and their attendants upon them for entertainment… or by insinuating themselves into their affections, and so getting to be the trustees of their estates, which they could make an easy prey of; for who could presume to call such as they were to an account? They aimed to enrich themselves…
4. A greater condemnation awaits those who hurt others in the name of God
5. We Must Not Exploit Others In God’s Name

a. Religious leaders still exploit vulnerable people for personal gain

i. Financial gain, emotional gratification, sexual fulfillment, influence
ii. Others exploit for religious reasons, hoping to earn favor with God
iii. Many have been obstructed from God b/c of abuse by a leader

b. Spiritual leaders have influence that can be used for God or abused for self

6. We must guard ourselves against being exploited in God’s name

a. Don’t be desperate for what people can give you or do for you
b. Don’t be manipulated in God’s name; ask others for their perspective, check God’s word about what someone might try to get you to do

B. They Zealously Recruited Converts V. 15

1. These men put forth great effort into making converts
2. Romans 10:1, 2 Brethren, my heart’s desire and prayer to God for Israel is that they may be saved. 2For I bear them witness that they have a zeal for God, but not according to knowledge.
3. Though they were extremely zealous, they were bringing people into damnation
4. “twice as much a son of hell”- perhaps referring to the zeal of a new convert, or perhaps those who were led astray from the true worship of God. They would not be guilty of never accepting God, but of accepting and then rejecting the truth
(Read 2 Peter 2, especially verses 20-22)
5. Religious effort, sincerity, & busyness is not the most important aspect of faith
6. There are many who are sincere & zealous, but are wrong about God
7. We may admire the efforts of others, and point to their zeal
8. Their zeal may be because of love for God, peer pressure, or earning salvation
9. We may ask why Christians don’t have such zeal. A fair question
10. But truth must be the starting point for any spiritual endeavor, not zeal
11. After knowing God through Jesus Christ, may we go on to be zealous for God

C. They Taught “Loopholes” Vs. 16-22

(How to be religious, and still live for yourself)

1. Loophole- “loop”- an ancient word for window opening, and of the vertical slits in the walls of medieval castles. Loopholes were used to shoot arrows through to defend the castle, but a wise enemy could find that narrow opening and penetrate the castle wall. Thus, a loophole is a small opening, or “out,” in a seemingly airtight law or command, which only the clever few can use.
2. Guzik- Out of obedience to God’s word, they would not swear by the name of God (Exodus 20:7). But they constructed an elaborate system of oaths – some of which were binding and some were not – a way of making a promise while keeping your fingers crossed
3. Instead of inventing loopholes & excuses, they should have loved God simply & honestly, & not developed ways to justify wrong behavior (See Matthew 5:33-37)
4. The result of “loophole Christianity” is self-deception, hypocrisy, a false assurance of salvation, & possibly damnation. How far might one go in living this way? How might we end up obstructing others from entering into Heaven?