She then spent four years at The Star where she worked on reporting police stories and the North American Free Trade Agreement's effect on Heinz's operations in Leamington, Ontario.

[13][9][14] Additionally, she was the lead journalist on a team that was a finalist for a Pulitzer Prize for National Affairs Reporting in relation to coverage of the Lehman Brothers and their role in the financial crisis of 2008.

[17][13][18][19] On October 1, 2016, The New York Times published an article authored by Craig and her colleagues David Barstow and Megan Twohey, which stated that Donald Trump had reported a loss of $916 million in 1995, which could have allowed him to avoid paying income taxes for up to eighteen years.

"[23] On October 2, 2018, the Times published a 14,000-word exposé co-authored by Craig, David Barstow, and Russ Buettner titled "Trump Engaged in Suspect Tax Schemes as He Reaped Riches From His Father.

"[24][25] The findings of the story was based on over 100,000 pages worth of documents, both public sources and private disclosures, that allegedly revealed the inner workings of Trump's financial practices and claimed misleading statements about his self-made wealth and business empire.

[32] In May 2023, a New York Supreme Court judge in Manhattan dismissed the lawsuit, concluding that Donald Trump's claims "fail as a matter of constitutional law" and that investigation into his finances was protected by the First Amendment.

[34][35] She has also spoken on-air about her reporting on Robert F. Kennedy Jr.[36] On February 22, 2024, Craig announced through an Axios exclusive that she would be publishing a book titled Lucky Loser: How Donald Trump Squandered His Father's Fortune and Created The Illusion of Success with Penguin Random House LLC in collaboration with her colleague Russ Buettner on September 10, 2024.

[39] Critics like Bethany Maclean of The Washington Post said "the news in their book lies not in one specific detail, but rather in the sheer accumulation of damning facts", while John Cassidy of The New Yorker praised Craig for making the argument that "he's a lousy businessman who only got as far as he did because of a series of lucky breaks that could paper over a litany of failure and still fund a lavish life.