New York AG Tish James is running for governor on her record of taking on Trump. But her role in the criminal probe of his company remains hazy.

• New York AG Letitia James has joined forces with the Manhattan DA for the Trump Organization investigation.
• She's also running for governor and touting her record of going after former President Donald Trump.
• Her office has scored wins against Trump on the policy front, but her exact role in the criminal investigation is unclear.

When New York Attorney General Letitia James announced her run for the governor's mansion in October, she highlighted some of her biggest cases. And she put 76 of them in one category.

"I've sued the Trump administration 76 times," she said. "But who's counting?"

James' challenges to former President Donald Trump fall into two categories, one of which went unmentioned in her announcement video.

There are the cases she brought against the Trump administration, including lawsuits trying to halt policies that she alleged protected predatory lenders, relaxed environmental rules, and discriminated against LGBTQ people.

"Defending the rights and wellbeing of New Yorkers and fighting for the powerless have always been my top priorities as attorney general," James told Insider in a statement, once again touting her office's 76 lawsuits. "For two years, my office stood up and fought the Trump Administration every time it tried to trample on the rights of New Yorkers and Americans across the country."

James also brought cases against Trump personally, including an investigation into the Trump Organization, which so far has produced a criminal indictment against the former president's company and its CFO, Allen Weisselberg.

Two prosecutors from James' office were cross-designated to work with the Manhattan District Attorney's office, which is leading the Trump Organization probe. Since the investigation is ongoing - prosecutors impaneled a second grand jury for the case earlier this month - there's limited public information about the machinations behind the probe, including what work each office has contributed thus far.

While James can't talk about the details because the investigation is ongoing, Daniel R. Alonso, a former top deputy for Manhattan District Attorney Cyrus Vance Jr., pointed out the information James' office gathered for its civil cases against Trump could be a major asset.

"My best guess is that what the attorney general's office brought to the table is a hell of a lot of knowledge about the Trump Organization," Alonso told Insider.

James has called out Trump from her perch as New York AG

James has approached her cases against the Trump administration with a special zeal. When he was in office, she used her position to get federal courts to halt policies she said trampled on civil rights issues.

"We filed 76 lawsuits against an administration that was hostile towards women, immigrants, people of color, members of the LGBTQ+ community, workers, and countless others; and we won over and over again," she told Insider. "Now, under the Biden-Harris Administration, we've seen decisive leadership that has protected young Dreamers, women, members of the LGBTQ+ community, and millions of others across New York and the rest of the United States."

James also scored a big win with her office's investigation into the Trump Foundation, which was forced to dissolve in 2019, though the civil lawsuit began under the tenure of her predecessor, Barbara Underwood. Trump admitted to illegally using the nonprofit's money for personal profit and to advance his political career.

In an interview with ABC's "The View" in December 2020, when asked about Trump calling her investigations against him "harassment," James basically launched into a campaign speech.

​​"With respect to the rant of the President of the United States since I've been in office these past two years - yes, my office has either led or joined 68 lawsuits against this administration. Protecting our environment, protecting immigrants, protecting the rights of women, protecting dreamers, protecting the Affordable Care Act, protecting the Postal Service and the list goes on," she said, adding: "It's important that the president of the United States understand that no one is above the law."

The law came for the former president's business after Michael Cohen, the former Trump Organization executive and personal lawyer for Trump, testified before Congress in February 2019. He alleged the company kept two sets of books: one to receive favorable bank loan and insurance rates, the other to pay little in taxes.

Both the Manhattan DA's office and the New York Attorney General's office were listening.

The offices then opened investigations, on parallel tracks, to examine the company's finances. Court filings and public announcements suggested they were each looking at whether the Trump Organization broke state laws by making hush-money payments to people who said they had affairs with Trump, by misrepresenting its finances, and by offering untaxed benefits to top employees.

James and the Manhattan DA joined forces

As recently as fall 2020, both prosecutors' offices had separate teams working what appeared to be the same leads. In an interview with Insider , Jennifer Weisselberg, a cooperating witness for both investigations, said that investigators from each office asked her about the same issues in separate interviews.

James' office distinguished itself in the following months with a series of announcements about the inquiries into the valuations of several Trump Organization properties as part of a civil investigation. Among them is 40 Wall Street, located just across the street from James' office in Manhattan.

The properties also include the Seven Springs estate in upstate New York, which the Trump Organization said in tax filings was used as a nature conservatory. Eric and Donald Trump Jr. said in media interviews that they used the estate as a summer home, however, and James' office successfully forced Eric Trump, now a Trump Organization executive, to sit for an interview.

Meanwhile, Vance's office put enormous resources into the case. It went to the Supreme Court twice to enforce a subpoena for the Trump Organization and obtain reams of tax documents.

Solomon Shinerock - the prosecutor in the DA's office who has been doing almost all the talking at the two public court hearings so far - said in September that the office had about 6 million pages of evidence for the charges against Weisselberg and the company.

Under state statute, the New York Attorney General's office has the ability to bring criminal cases under only a few areas of law. Otherwise, it needs a referral from the governor's office or state legislature to pursue a wide-ranging criminal investigation.

The office can also "cross-designate" its attorneys with a district attorney's office, which is what happened for the Trump Organization investigation. Earlier this year, two prosecutors on James' team were basically loaned out to the Manhattan DA's office. The team-up saves work for everyone, Alonso said.

"If somebody's already gathered evidence, and they've already cataloged that they've already interviewed witnesses related to it - there's a value in accelerating that part of the investigation," Alonso said. "So it makes sense to team up."

The DA and AG offices jointly led a criminal investigation, while the AG's office has also continued its civil probe. In July, the prosecutors on the criminal case filed a 15-count indictment against the Trump Organization and Weisselberg, accusing the executive of evading taxes on income and benefits like a free apartment. Vance and James walked side-by-side that day into court, where the company and Weisselberg pleaded not guilty to the charges.

"My office remains committed to enforcing the law and holding accountable those who abuse their authority - no matter how powerful," James said in the statement to Insider.

Vance will retire on December 31 after three terms as DA, and on January 1, Alvin Bragg will take over. Bragg is a former top official in the New York State Attorney General's office himself, leaving two weeks before James took office. He's widely expected to keep the same tack as Vance.

"My approach to this case will be the same as mine to every case: follow the facts and deliver justice for New Yorkers," Bragg told Insider in June. "That's what we did in the Attorney General's office where I led the team that sued Trump and his administration more than 100 times, including successfully suing the Trump Foundation, removing the citizenship question from the census, and challenging the travel bans and other unlawful policies."

Running for governor as a sitting AG is a tradition in New York politics

In Albany, James has earned a reputation as a shrewd operator and a rising star in the Democratic Party. As the state's attorney general, she's in the process of suing the National Rifle Association into oblivion, and her office's investigations and litigation has shut down consumer scams and led to hundreds of gun buybacks. Nearly every day, her office issues a press release about cases against predatory lenders and opioid deaths.

Now that the gubernatorial primary is open, lawmakers are weighing whom to support, or whether to stay out of the race altogether as Democratic Gov. Kathy Hochul implements her agenda while trying to secure a full term.

For Assemblyman Phil Steck, an Upstate Democrat from Schenectady who has yet to endorse a candidate, James' record on antitrust enforcement and opioids carries more weight than her challenges to Trump.

"I'm a fan of the attorney general for two reasons," Steck, who endorsed James' rival, Zephyr Teachout, in the 2018 AG primary, told Insider. In that primary, disgraced former Gov. Andrew Cuomo endorsed James.

"First, since she's been attorney general, I think the office has done a lot of outstanding work in many areas that protect the public interest," Steck continued. "Two, she has a long history of progressive politics. So in comparison - while I know the current governor very well and like her - the reality is that the new administration is surrounding itself with a very similar aura to that which existed when Andrew Cuomo was governor."

Changing how business is done in Albany could be a very powerful message for the James campaign following nearly three full terms of the Cuomo administration, Steck said. But he added that the AG's Trump investigations could play well in a primary atmosphere.

"I think from a strategic standpoint, what Tish James is doing is trying to show to Democrats that she was someone who was willing to take on Donald Trump," the assemblyman said.

But did James's lawsuits against the Trump administration - often filed in concert with other Democratic state AGs - result in substantial change? One Democratic operative told Insider they didn't think so.

"Clearly Tish used Trump to raise her profile, and you see that in the announcement video," a longtime Democratic New York political operative, who plans on sitting out the 2022 gubernatorial primary campaign, told Insider.

"You know who's counting? The people who have seen zero results out of this," the operative continued. "To voters in New York and Democrats and donors across the country who were resting their hopes on Tish James, she's delivered bupkis."

Given that attorney general has been a well-trodden springboard for Empire State gubernatorial hopefuls - Cuomo ran on a "Clean Up Albany" slogan when he secured the top job - James' ability to showcase her record could make or break her campaign, according to the longtime state political operative.

"New York attorney general is one of the best perches for a push to run for office," the operative said. "Ask Elliot Spitzer. Ask Andrew Cuomo. Right? Elliot Spitzer, sheriff of Wall Street, took down titans in the financial industry - what did Tish do? She filed a few lawsuits against Donald Trump?"

From the perspective of rival campaigns, the operative argued, there's an opening to to turn the primary electorate's anti-Trump fervor against James in a "boomerang" fashion.

"I do believe that you are going to see her Democratic opponents saying, 'Tish, where's the beef?'" the operative said, referencing the 1980s ad campaign from Wendy's. "So yeah, I think it's going to be a problem."

Yet for a potential key Upstate endorsement like Steck, that decision won't hinge on James' Trump investigations.

"I'm just stressing the point that for me, when my decision as to who I might support for governor is announced, it's not going to be based on Donald Trump," Steck said.