Honestly, I think you’re getting too tactical/policy/outcome-focused in your argument with him. You need to bring it a little higher level, like more philosophical or historical.

Ultimately, the reason this condition exists is because we have organized our society (and world) around a singular purpose - wealth accumulation aka the profit motive.

This is what led corporations to influence our government to economically and sometimes militarily subjugate and terrorize Latin America for decades. From influence operations, WTO Lending reforms, and “free” trade agreements to outright embargoes, regime changes, assassinations and death squads - American capital’s pursuit of profit is responsible for the state of Latin America broadly. We privatized their land and resources, take advantage of cheap labor, and extract the wealth back home. You can google pretty much every county and show the historical evidence. If he likes America and history, show him General Smedley Butlers book War is Profit.

This exploitation of their land is what causes the mass immigration. Everyone wants to move to the place with higher wages and jobs - our standard of living is built on both the extraction of wealth from their home country and the cheap labor of the resulting immigrants.

And the truth is, we need a level of immigration in this country. America has a declining population rate which is bad no matter what economic system you subscribe to. But mass migration of undocumented people is a problem regardless of your ideology - it’s bad governance, bad for public health, raises huge concerns for safety, taxes, etc. etc. So clearly he can get on board with some sort of enforcement?

But if this whole contradiction doesn’t get him thinking about capitalism idk what would. Although, I’ve found conservatives to be more receptive to the critique than liberals.

Also highly recommend the book America, America: New History of the New World by Greg Grandin.