The question isn’t how Rudy Giuliani’s career choices led to this place. What he needs to decide now is where he wants to go.
Longtime Rudy Giuliani aides and colleagues are at best perplexed by the 9-11 mayor’s recent media appearances. Many are actively embarrassed for him.
They just can’t figure out what Rudy is getting out of becoming a media punching bag or, depending on who you talk to, informal Trump administration bag man.
After all, the president’s last personal lawyer ended up both behind bars and disbarred for crimes on behalf of a client. Michael Cohen will never practice again.
To avoid a similar fate, Rudy needs to thread the needle between keeping his nose clean and remaining effective in his role.
A professional reputation is a lot to throw away for a pro bono case. Everyone who works with high-profile people needs to understand the calculus here.
Unless he has something amazing in reserve, it isn’t going to happen. And in that scenario, Rudy’s once-bright future has gotten cloudy.
Professional double bind
Rudy is officially the president’s private lawyer. Whatever high-level legal expertise he’s deploying behind the scenes, he really functions as an attack dog right now.
That’s the role he plays and the value he provides. He’s a surrogate who goes where rule-following government employees can’t.
Arguably it’s also the role he played negotiating for foreign governments as well. When the official communications channels hit a wall, Rudy showed up.
Unfortunately, when his “professional associates” got arrested for spreading the wrong campaign donations around here at home, the situation got unsustainably complicated.
Rudy’s friends got picked up at the airport trying to flee the country a day after he had lunch with them.
They must have been under surveillance. And as far as we know, the FBI didn’t bother interviewing him, which must have provided a shudder or two when you’re the man who put Frank Gotti away.
He knows the procedures. He knows the tactics. If your associates are being monitored, they’ve probably got you on tape.
And that’s where the problem is. Client communications are privileged except when they advance a crime. Campaign finance violations are crimes.
Likewise, presidential communications are privileged, except when they’re used to commit crimes.
If Rudy talked about anything awkward with his friends, he can either accept personal responsibility or say he was pursing the president’s interests.
Unfortunately, the shadow of impeachment means that the administration wants to distance itself from all things Ukrainian at exactly the moment Rudy wants to brag on TV about how closely he was working with the White House.
He wants presidential cover. They don’t want to answer questions about why the president’s private lawyer was involved so intimately in foreign policy.
After all, he isn’t a diplomat. He isn’t even a government employee. Any privilege here is presumably between private citizens.
Or if it isn’t, then the White House needs to address how that line blurred and where responsibility rests. They don’t want that.
It’s a fundamental question of where the personal and professional loyalties balance. Like any advisor in a tough spot, Rudy gambled his career on that calculus.
The real solution is of course not to get in a tough spot in the first place. Refuse all requests to blur the roles. Outsource conflicts of interest.
You can usually find a colleague who can relieve the conflict. If not, the entire proposition is probably a bad idea.
And if the conflict is between you and your client, the rules change. Self-preservation becomes the primary motive unless you’re happy repeating Michael Cohen’s career arc.
Cutting the attack dog loose
For some in the administration, I suspect Rudy is now part of the problem. Every time he talks about Ukraine, even just to defend himself, it casts shade back on the White House.
They’re in a bind too.
The attack dog loves to brag about how close he is to the White House. Even if they could shut him up, it leaves a void in their media profile.
Unfortunately for them, nobody in a more conventional media role is going near this topic. Normally we’d see press conferences and policy advisors making the TV rounds to explain the diplomatic logic here.
Sunshine is a great disinfectant. It makes misunderstandings go away before they turn into outright scandals.
Rudy knows that too. He knows how to tell a simple, unembellished story anchored at every point by public record and fact.
Secrets, on the other hand, drive the news cycle. Ambiguity is practically as bad, generating conspiracy theories that are extremely difficult to eradicate.
But when intrinsic conflicts make transparency impossible, you’re in trouble. Rudy tends to shoot from the hip, not from the script. You can coach him but he’s his own boss.
Think of dysfunctional organizations you’ve worked in. People who need information don’t get it. They need to fill in the gaps to the best of their ability, and they inevitably do it wrong.
In those scenarios, the important thing is being able to land on your feet when you get out. You need to have a career on the other side.
Rudy is 75. This should be a career-defining peak for him, the prelude to a long and lauded retirement.
Unfortunately, he’s also in the middle of one of his more venomous divorces. Previous splits left him practically bankrupt.
He needs a lucrative exit here. Maybe that’s what he saw.
Polling on impeachment has spiked against the White House since his troubles began. He’s no longer useful.
Like any advisor in a situation where there’s no longer any value for all parties, it’s time to pull the parachute cord.
Let go of the relationship. Salvage your pride and your reputation. Find other things to do.