Jamieson, Fausset and Brown on Philippians 1:20

20. According to my earnest expectation--The Greek expresses, "expectation with uplifted head (Lu 21:28) and outstretched neck." Ro 8:19 is the only other place in the New Testament that the word occurs. Tittmann says, in both places it implies not mere expectation, but the anxious desire of an anticipated prosperous issue in afflictive circumstances. The subject of his earnest expectation which follows, answers to "my salvation" (Php 1:19).

in nothing I shall be ashamed--in nothing have reason to be ashamed of "my work for God, or His work in me" [Alford]. Or, "in nothing be disappointed in my hope, but that I may fully obtain it" [Estius]. So "ashamed" is used in Ro 9:33.

all boldness--"all" is opposed to "in nothing," as "boldness" is the opposite to "ashamed."

so now also--when "my body" is "in bonds" (Php 1:17).

Christ--not Paul, "shall be magnified."

life, or by death--Whatever be the issue, I cannot lose; I must be the gainer by the event. Paul was not omniscient; in the issue of things pertaining to themselves, the apostles underwent the same probation of faith and patience as we.