Sorting based on milestone dates

I thought this was simple but now I'm utterly confused

My current project shows orders by milestone date/times. these dates are linked back to a date calendar by delivered date. The effect of this is to sort the table by our delivered date.  

table, Date selected June 1st, 2018

I've got a request asking if they can have a slicer that will sort by a different milestone..OK!?

What I tried and Failed

I created additional columns that returned dates for the specific milestones. Then created inactive relationships for my date calendar and created a new modified measure.

base measure,

Measure 1

milestone = max(enteredOnDate)

Measure 2

Arrival= calculate ([milestone], userelationship(milestone,calendar[date)).

I expected This (manually created for illustrative purposes)

A milestone table sorted by Arrival/Pickup showing all other relevant dates but I ended up with this below. 

A table filtered to only Arrival/Pickup dates...

I'm missing something obvious here.

please help.

Thanks!