Richard Blumenthal

“I’m the last person to ask what is on Trump’s mind,” Sen. Richard Blumenthal says. | Alex Wong/Getty Images

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A long-running feud over New York City real estate may play a part in the ongoing attacks on Sen. Richard Blumenthal.

He’s not a household name. He’s not running for president. Yet Richard Blumenthal keeps getting under President Donald Trump’s skin.

Every few months, the president unleashes on the Connecticut Democrat by ridiculing his military service record, a surprising attack on a rank-and-file Democratic senator by the commander in chief.

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Blumenthal dutifully votes against many of the president’s nominees and is quick to raise questions about his administration and even the president’s family, yet is not exactly as well-known as Sens. Elizabeth Warren or Chuck Schumer, two of Trump’s other favorite targets. But Trump’s beef against Blumenthal is multifaceted, spanning from family drama to digs at the senator’s military service — though Trump has faced questions about his own deferments during the war.

There’s also Blumenthal v. Trump. The former Connecticut attorney general took the high profile step of suing the president in 2017 for allegedly violating the Foreign Emoluments clause of the Constitution. So when the president attacks Blumenthal, he does so with the same intensity that he goes after someone like Warren or House Intelligence Committee Chairman Adam Schiff (D-Calif.).

On Monday, the president tweaked the second-term Democrat again, his 12th tweet attacking Blumenthal in the past two years. That’s 11 more than Sen. Kirsten Gillibrand (D-N.Y.), who is running for president, has received from Trump. The president often tweets about Blumenthal after the senator makes a public comment about the president.

“How does Da Nang Dick (Blumenthal) serve on the Senate Judiciary Committee when he defrauded the American people about his so called War Hero status in Vietnam, only to later admit, with tears pouring down his face, that he was never in Vietnam. An embarrassment to our Country!” Trump fumed.

The missive came just minutes after Blumenthal told Rachel Maddow on Monday that he had issues with Donald Trump Jr.’s “truthfulness” in testimony before the Judiciary Committee.

Several senators, including the Connecticut senator himself, said they were at a loss as to why the president would respond to Blumenthal in such a fashion, even given Blumenthal’s long-running animus toward the Trump administration.

“You’ll have to ask him. My only comment is ‘there he goes again,’ really too ludicrous to merit a response,” Blumenthal said in an interview.

Trump’s beef against Blumenthal has many parts. There is his military service. But Blumenthal’s in-laws and Trump share a tangled web, a family feud that goes back decades into the New York real estate scene and has accelerated the president’s attacks on Blumenthal.

The senator has admitted in the past he misstated serving in Vietnam, though he served in the Marine Corps Reserve during the war.

“Trump gets a bad rap for not serving in the military,” said a former senior White House official, so when he realized Blumenthal had his own issue, the president “seized” on it.

But Blumenthal’s in-laws and Trump go way back in New York real estate circles. Trump and Blumenthal’s father-in-law, Peter Malkin, were competitors in the Manhattan real estate market and eventually clashed over a deal involving control of the iconic Empire State Building.

Those clashes have intersected with Blumenthal’s status as a Democrat who is among “the most vocal on Trump’s potential legal liability,” said Sen. Chris Murphy (D-Conn.).

“Their families traveled in the same circles,” Murphy said. And Blumenthal “is picking a scab regularly that Trump’s particularly sensitive about. Dick’s on TV a lot talking about the Mueller investigation. He doesn’t pull any punches.”

The Democratic senator is among the chattiest in the Capitol, quick to find ways to weigh in on the issue of the day. His colleagues say he’s keen on the Schumer press strategy of identifying and seizing buzzy issues. He’ll often spend long sessions going back and forth with reporters in the basement of the Capitol.

And Trump’s attacks on Blumenthal only amplify the voice of a senator who’s often finding ways to break into the news.

“For Blumenthal’s audience, it probably helps him” to come under attack, said Sen. John Thune (R-S.D.).

Murphy said the family history between Blumenthal and Trump was best left to his senior colleague, but Blumenthal is not eager to address either Trump’s specific criticism of his military service nor the president’s fixation with him.

“The simple answer is. I have no idea,” Blumenthal said on Tuesday. “I’m the last person to ask what is on Trump’s mind.”

The real estate dispute stretches back more than 20 years, when Trump in 1994 claimed that he purchased 50 percent of the title to the Fifth Avenue skyscraper, which was controlled by Malkin and his partner, Leona Helmsley. In 1995, he sued to get the lease broken by accusing Helmsley of violating its terms due to improper upkeep of the historic building.

Both parties battled for ownership in court until a Manhattan judge denied Trump’s petition in 1999. Trump’s attorneys accused Malkin and Helmsley of allowing the building to become “second-rate” and infested with rodents. Trump appealed, lost, and eventually agreed to sell his portion of the lease to Malkin for $57.5 million in 2002, according to reports at the time.

That’s so long ago that most senators and White House aides have no idea it occurred or that it colors Trump’s beef with Blumenthal. But Trump isn’t one to give up a grudge so easily, especially when Blumenthal is so quick to mix it up with the president. He called the president an “unindicted co-conspirator” at the end of 2018 for covering up hush money payments.

The White House did not respond to a request for comment.

Asked why Trump goes after Blumenthal, a former Trump campaign aide replied: “It’s the way [Blumenthal] talks on TV. He speaks with certainty.”

Blumenthal “was saying Trump was going to be indicted by the end of the year. So from Trump’s point of view, he likes characterizing this guy as a total fraud so that every time he speaks nobody takes him seriously,” the aide said.

A spokeswoman for Blumenthal disputed that characterization and said that the senator “hasn’t ever said that President Trump would be indicted, let alone given a time frame.”

And people who know Blumenthal say the relationship is all the more awkward because they ran in similar New York-area social and political circles, particularly when Trump was still donating to Democrats.

“Trump’s lineage was in the Democratic Party for a long time so they have a lot of overlapping relationships in New York and Connecticut,” said a GOP lobbyist.

Trump first went after Blumenthal in February 2017, after the senator met with then-Supreme Court nominee Neil Gorsuch and said Gorsuch called Trump’s attacks on the judiciary “demoralizing.” Ever since then, the president has whacked Blumenthal at regular intervals, almost always concentrating on his military service.

“You’ll notice that the president is very repetitive,” said Sen. Mazie Hirono (D-Hawaii). “He latches onto something and he never lets go.”

Of course, Hirono has been just as critical of Trump over the past two years. Asked why Trump has gone after Blumenthal so much and not her, she answered: “I don’t know, you should ask him.”

Then after a pause, she thought better of it: “Well, no, don’t.”

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