[5] He was a photographer with The Chicago Tribune, stationed at the Washington, D.C., bureau from 1998 to 2007; during this period, he also followed the rise of then-Senator Obama to the presidency.

In 2004, Jeff Zeleny, now a political correspondent for CNN, asked Souza to take photographs for a project documenting Barack Obama's first year as a U.S.

He documented Obama's time in the Senate, following him on many foreign trips, including those to Kenya, South Africa, and Russia.

[6] Souza's photograph taken at 4:05 pm on May 1, 2011, in the Situation Room during the raid on Osama bin Laden, featuring Obama, Vice President Joe Biden, Secretary of State Hillary Clinton, and others, quickly became an iconic image.

Jacob asked if Obama's hair was similar to his and the image has become symbolic of the African American struggle for civil rights.

[21] As the official White House photographer, Souza traveled with the president to document each meeting, trip and encounter for historical records.

[27] Upon Donald Trump's inauguration as president in 2017, Souza began sharing pictures of Obama on his Instagram account, often as critical commentary on the new administration.

[31] In January 2021, Souza gave advice to Adam Schultz, the incoming Chief Official White House Photographer for President Joe Biden.

He also noted that the photographer for outgoing President Trump, Shealah Craighead, had posted "very few behind the scenes pictures" to Flickr during her tenure.