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That morning, Lawsky spoke to a crowd of financial journalists and industry types in a place so lush, white, and hushed, it feels like being inside a roll of expensive toilet paper. When Lawsky told the crowd that Massachusetts Senator Elizabeth Warren, Wall Street–basher-in-chief, was "brilliant" and "someone worth listening to," the silence was profound.
Afterward, Lawsky briefly spent time taking reporters' questions and pressing the flesh. In person, the 43-year-old civil servant is almost comically clean-cut, the type of man you imagine stepping out of the shower completely dry, clad in a suit and polished wingtips. He doesn't deny he has been hard to reach the past few months.
"I'm shy," he says, chortling dryly at his own joke before quickly turning serious. "No. I think that—you know, I don't think DFS should be about a cult of personality. I don't want it to be about any one person."
He comes off distinctly unpolitician-like; he doesn't try to deflect conversation about hostilities between himself and federal regulators and doesn't seem to have a canned, sunny answer about it. These days, he says flatly, the relationship between DFS and the feds is "fine."
True, "We shook things up with Standard Chartered. We said, 'We think this should be done in a different way.' But I think since then things have settled down."
Tensions between regulators are to be expected, Lawsky says. "But in a healthy competition, everyone is sorta pushing each other to do more and be a better regulator. And that's much better than the alternative, which is unhealthy competition, where it's who can be the lightest-touch regulator. Then you have standards moving downward."
Art Wilmarth, a law professor at George Washington University and a student of federal-versus-state regulator strife, says there's a history of the feds resenting the more aggressive actions of states like New York. Lawsky may be smart to keep his head down, out of the line of fire.
"The best he can hope to do is embarrass his federal colleagues so they sort of have to fall into line," Wilmarth suggests. "Eliot Spitzer did that for two or three years in the early 2000s. And there's no question he paid a price. I think he picked up a lot of enemies on Wall Street."
If it's tough to pin down Lawsky for an interview, it's nearly impossible to get the financial industry to speak his name—at least not on the record.
Told that a background conversation would have to be paired with an on-the-record statement for this story, Deloitte spokesman Jonathan Gandal countered by agreeing only to "fact-check" the article and "consider" submitting a statement for publication. (Deloitte did not provide the latter.)
The Securities Industry and Financial Markets Association, one of Wall Street's largest trade groups, also declined to comment.
Following numerous requests over the course of several weeks, the New York Bankers Association relayed a one-paragraph statement calling Lawsky "diligent" and adding that he "maintains an open door policy, and always listens to our concerns." Several other banking associations and trade groups didn't reply to multiple interview requests.
"We don't discuss our regulators publicly and we're still under a consent order," says Julie Gibson, a spokeswoman for Standard Chartered. When pressed, she adds, "They've got all the cards. It's not a relationship of equals. If you make them mad, then, you know . . ."
She opts not to finish that thought.
As he stood in the Yale Club's overstuffed ballroom, Lawsky had to be aware of his new position: feared and loathed in some corners, respected in others, but very closely watched. He has the capacity now to make people nervous, as he clearly did during his speech when he mentioned that DFS was about to turn its attention to the state's pension funds.
"Our predecessor agency did somewhat limited reviews and published them rarely," he said. "We're going to change that and significantly step up the scrutiny."
The comment generated a flurry of news reports; one Capital New York reporter immediately tweeted that Lawsky's words were "a warning shot."
The same thing happened in early August, when DFS announced it would look into Bitcoin, the online currency that's basically unregulated in the offline world. When DFS homes in on a target these days, people listen.
But Lawsky also seems uncharacteristically nervous about coming across as "anti–Wall Street," taking pains during the Yale Club event to make it clear he's as pro-business as anybody.
"I think taking real, appropriate, and sometimes tough action is not anti-business. It's pro-business because it protects our system, keeps up consumer confidence and ultimately helps prevent another meltdown," he told the crowd.
Yet his agency is essentially fighting a guerrilla war: running out of the jungle, picking off the targets it can reach, then retreating. It's outmanned by a financial system—an entire economy—that's been bent and twisted to serve the needs of the insurance and finance industries, with enthusiastic help from politicians who rely on donations from those sectors and regulators seeking lucrative landing spots at these firms someday. From this angle, Lawsky's job starts to look like a morbidly depressing game of Whac-A-Mole.