1)

How will Shakai be "b'Tzarecha"?

1.

Rashi #1: If Shakai refers to Hashem, this is astounding. Is this a curse, that He will be among your enemies, like "v'At Hayis b'Ocherai"?! The verse must be abbreviated, e.g. Shakai will judge Tzarecha.

2.

Rashi #2: Perhaps Shadai is not Kadosh. It is a judge, or strength. The strength of your fortresses will be like "v'Shis Al Afar Batzer" - in a fortified place. The Seifa supports this (refer to 22:25:2:1).

3.

Ibn Ezra #1: Your Kesef will be strong. This is like "k'Kol Shakai." This Perush is primary, for it is the Seifa.

4.

Ibn Ezra #2: He will be with you in your afflictions, like "Imo Anochi v'Tzarah."

5.

Devar Eliyahu: Shakai will be Mivtzarecha (your fortresses); He will strengthen them.

6.

Malbim: Shakai will be your fortress. You will find strength in Him, and protection from all enemies.

2)

How is "v'Chesef To'afos Lach"?

1.

Rashi: This is strength, like "k'So'afos Re'em Lo." Ibn Ezra - this repeats the Reisha (your Kesef will be strong).

2.

Devar Eliyahu: Kesef will fly to you, like birds fly. These two verses correspond to Chesed and Gevurah.

3.

Malbim: This is not like Kesef buried in the ground, rather, like Kesef that flies above. It is desire for supreme spirituality.

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