“Lowly in spirit” is more about humble on the inside (character) and “the oppressed” is more about circumstances on the outside – poor, humble lifestyle and beat down by the system.
“To share plunder with the proud” is not about just having riches. “Plunder” is something taken in victory over someone else. These are folks who have defeated others and what they “share” doesn’t really belong to them!
While it might seem to be way more fun hanging with them, this wise saying suggests it’s not. Instead, it’s better to be humble on the inside and hanging with those who have little or nothing.
What the verse doesn’t say is why this is better, but that’s not hard to figure out.
If we’re hanging with the plundering proud, it’s only a matter of time before someone comes after them. We might become collateral damage in their demise!
Or, hang out with them long enough and there’s a good chance, at some point, they’ll turn on us and plunder us!
Besides, in God’s economy, life’s not supposed to be about stuff or feeling like I’m in control. Jesus said something about “blessed are the poor in spirit…” (Matthew 5:3).
Beats hanging with the big dogs every time!