The names of these two Jewish Aristocrats deserves attention because
the names they were given in the Megilah were not their real names. Machlon comes from the word " Mechila " meaning forgiveness. It is
possiblethat someone could call their child by that name but we don't
find it used as a name elsewhere.
Chiliyon however is decisive as it comes from the word " Caliya " meaning destroyed. No Jewish parent is going to call there child that!
The Alshich says that the Prophet Shmuel who wrote the Megilah was
telling us their natures and fates. Machlon was forgiven where as
Chiliyon was destroyed.
How was Machlon forgiven if both died for their mistakes?
The answer takes into Kabbalistic thought.
Judaism teaches that the souls of people can be reincarnated ( in fact one of the greatest Rabbis of the generation told me that most of us have been here before ) in order to repair the damage done in a previous life or to achieve things not before achieved.
When Rus remarried a relative of hr dead husband's, Boaz , she gave birth to someone named Ovaid. Ovaid was Machlon ! Her first husbands soul was reincarnate as Ovaid who's son was Yishai who's son was David HaMelech.
But why if both brothers did the exact same things; either marrying out of abandoning Eretz Yisroel should one be forgiven and the other not?
If you examine the text of the Megilah you find in the fourth verse.......
" And they married Moabite wives. The name of the first was Orpa and the name of the second was Rus "
If we realise that Machlon was the older brother and Chiliyon the
younger and that Machlon married Rus; we have the key to the puzzle.
It was Chiliyon who married out first. Machlon who one would have
expected to marry first refused to marry out until his brother by his own marriage broke his resolve. It is far harder to hold out against you
" Yetzer Ha Ra " when he can Point t to someone else and say.....
" Look at him or her, they did it you should too! " It was only when Eve ate from the tree of knowledge that Adam gave in and ate too. Naomi
applies the same Psychological verity in trying to dissuade Rus from
continuing to accompany her to Israel and her eventual conversion.
In verse fifteen she says " And she said look! your sister in law has returned to her people and to her gods. Return like your sister in law "
The Megila establishes a fundamental principal regarding Ha Sh-m's reaction to Chiliyon and Rus and those who emulate them.
A Jew who not only flaunts crucial Jewish law but cause others to replicate and repeat the offence receives the severest punishment.
Those like Rus who are able to maintain their direction in the face of fashion and peer pressure can expect superb reward. In Rus' case it
meant becoming the mother of the Davidic line which leads to the Moshiach.