After earning his master's degree, Grim worked as a legislative analyst for the
Marijuana Policy Project. Grim has written about the history of
drug use and
drug culture in the United States. He has presented his research on why drugs are popular at certain times in history and his thoughts on the government's
war on drugs. He also worked as a
stockbroker in
New York City from 2000 to 2001. Grim joined
HuffPost (then
The Huffington Post) in January 2009. Towards the end of his tenure at
HuffPost, significant leadership changes were occurring, sparked by
Arianna Huffington's exit. In 2016, Grim published a blog post in which he questioned
FiveThirtyEight models and predictions for the
2016 United States presidential election.
FiveThirtyEight had predicted that Trump had a greater chance of winning the election than that predicted by other analysts.
FiveThirtyEight founder
Nate Silver responded to Grim's criticisms. After Trump won the election, Grim apologized, tweeting "You were right that there was far more uncertainty than we were accounting for. I apologize. Gonna stick to punditry".
The Intercept Grim left his position at
HuffPost in 2017 after nine years with the paper, joining
The Intercept to head its Washington, D.C. bureau. During the
Brett Kavanaugh Supreme Court nomination, Grim was the first to report that
California senator
Dianne Feinstein had received a letter related to
Kavanaugh, later revealed to be from
Christine Blasey Ford, alleging that Kavanaugh had sexually assaulted its author in high school. Grim also reported on former Trump aide
Rob Porter's abuse allegations by his ex-wives. He reported early on the 2018 campaign of
Alexandria Ocasio-Cortez. In 2023, Grim obtained and published a leaked Pakistani
diplomatic cable alleging
U.S. State Department pressure on the Pakistani government to remove Prime Minister
Imran Khan from office in 2022.
Drop Site News In July 2024, Grim and Jeremy Scahill, the co-founder of
The Intercept, founded
Drop Site News. Although there was previously friction between the pair and
The Intercept board,
Drop Site is backed with some funding by
The Intercept. In February 2025, Grim and
Drop Site News broke the story that the
U.S. State Department had allocated $400 million for "Armored
Tesla" in a procurement document. After the story broke, the document was amended to read "Armored Electric Vehicles" instead. The story prompted Senator
Richard Blumenthal and Congressman
Gregory Meeks to send letters to Secretary of State
Marco Rubio highlighting the
conflict of interest in
Elon Musk's role as CEO of Tesla while also working for the
Department of Government Efficiency.
Breaking Points Grim joined Breaking Points in 2022 as a co-host alongside
Emily Jashinsky, after leaving
The Hill's Rising. Two pair hosted the show on Tuesdays, named Counterpoints. As of 2026, Counterpoints has been dissolved, and Breaking Points has incorporated Jashinsky and Grim into the program throughout the week. Grim co-hosts the show frequently alongside Jashinsky or the other co-hosts,
Enjeti and
Ball.
Publishing Following the move to
The Intercept, Grim and Alex Lawson established Strong Arm Press, a small imprint printing press. Grim launched the press because he felt that the
first Trump administration was moving too quickly for the standard publishing cycle, which takes around a year to publish a book. He launched Strong Arm Press to accommodate shorter, cheaper, lower-volume books with a shorter publishing turnaround time. The first title published was
Out of the Ooze, a profile of
Tom Price that reached
Amazon's
top 100 list. Books are funded through
crowdfunding campaigns. Grim published ''We've Got People
, a history of progressivism and the Democratic Party, through Strong Arm Press in 2019. In 2023, he published The Squad: AOC and the Hope of a Political Revolution.'' == Personal life ==