Judge Andrew Napolitano said Wednesday on “The Laura Ingraham Show” the U.S. should “expect another round” of “extraordinary” prison sentencing commutations from President Obama before he leaves office Friday.

In the waning hours of his presidency, Obama caused consternation Tuesday evening when he commuted the sentence of former Army private Chelsea Manning and 209 others. Manning, who leaked a myriad of classified materials to WikiLeaks, had been serving a 35-year sentence. Her sentence now will end May 17.

“I will tell you this: We have learned at Fox to expect another round of these before Friday morning, which would be this afternoon or tomorrow.”

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“I don’t know what motivated Barack Obama,” Napolitano, the senior judicial analyst for Fox News, told LifeZette Editor-in-Chief Laura Ingraham. “I will tell you this: We have learned at Fox to expect another round of these before Friday morning, which would be this afternoon or tomorrow.”

With Tuesday’s commutations, Obama has issued a total of 1,385 since taking office, the most number of any president in U.S. history. But Manning’s commutation may be the most controversial of them all.

“I was surprised to see it. I was surprise because it was his administration, his Justice Department, that prosecuted Manning when [Chelsea] was Bradley Manning,” Napolitano said. “They could have charged [Manning] with treason … because somebody died, more than one person died as a result of what [Manning] did. They didn’t. But they did prosecute [Manning] aggressively.”

Saying that the Obama administration “has prosecuted leakers far more aggressively than any administration of the modern era,” Napolitano said he could not fathom why Obama let Manning off the hook. If Obama had asked Secretary of Defense Ash Carter, Secretary of State John Kerry or CIA Director John Brennan, Napolitano said they most likely would have given Obama advice “contrary to what he did.”

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“So something in Barack Obama motivated this extraordinary act. I don’t know what it was,” Napolitano said.

“If you look at this from a moral perspective, the harm caused that the government can quantify is extraordinary. Another moral perspective is: What is mercy? It is the opposite of justice. Justice is giving a person their due. Mercy is often given when it is undeserved,” Napolitano said.

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“And what motivates presidents to be merciful at the end of their term? Something within them? A desire for legacy? A willingness to please certain groups that are part of their base?” Napolitano continued. “I can’t exactly put my finger on it.”

Napolitano did posit the idea that perhaps Obama acted in this case out of some desire to cater to liberal activists who have held up Manning as a transgender hero.

“He knows that the vast majority of what he did, which he in his heart believes is right … is now going to be undone by a maverick Republican president and significant Republican majorities in the Congress,” Napolitano said.