Like what Booth and company tried to do with Abraham Lincoln? Yeah, it should be very hard to do, near-impossible, reserved for highly skilled Liberals.
You'd have to coordinate the two assassinations to be absolutely simultaneous; you couldn't have even a minute between them. With the Lincoln assassination, there wasn't the ability to send messages near-instantaneously, and most of the targets were unaware that anything was going on; but in the time that LCS is set in, cell phones and live video mean that you'd have maybe one or two seconds of leeway between assassinations, if that. Any more and somebody raises the alarm and the secret service is all over whoever you haven't shot yet.
Secondly, you'd need to trust your assassins. One person alone can just use a sniper rifle and take out the target, or whatever. But more than one person, a conspiracy, and things fall apart--somebody talks (a risk with low Heart, low Juice, or high Wisdom), or somebody finds they just can't go through with it (high Heart or low Juice), or somebody messes up the timing.
There's also the problem of reputation. Even the people who don't like the President are usually still pretty pissed if someone kills him. So this could totally backfire. Only in a country where the LCS is loved by most and the President is hated by most would this be a profitable move.
It should also bring an automatic Treason charge for the entire LCS membership.
It should be complex, difficult, and worth trying only if you are very skilled. It is theoretically possible, though.