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In the case of Hillary's server, it was illegal to use for State Department business, and it did contain classified info. Also, the reason she set up this server in the first place was so she could keep the graft box she set up out of public records.
I doubt he discuses classified info over that phone or any unsecured land-line phone.
Trump using his iPhone is not illega
Obama: If Republicans really cared about Clinton's
Who cares about either of them?
https://thehill.com/blogs/blog-briefing-room/news/413423-obama-if-republicans-cared-about-clintons-emails-they-would-be