How has it worked out for those that joined the Trump organization previously?
That depends on the case. Whom do you have in mind?
Jeff Sessions (AG)? He wimped out.
Rex Tillerson (State)? Trump was leveraging his oil and gas experience, but Tillerson began undermining Trump.
Reince Priebus (Chief of Staff)? He personified establishment GOP.
John Kelly (Homeland/Chief of Staff)?
James Mattis (Defense)?
Kellyanne Conway (Advisor)?
Someone else?
-PJ