Following his re-election in 2022, attempts were made to disqualify him from office due to his membership in the far-right Oath Keepers militia after the group participated in the January 6 United States Capitol attack.

[4][5] After graduating West Point, Eastman joined the United States Army where he was a military police captain stationed at Fort Richardson from 2003 to 2011.

[10][11] On January 22, 2024, Eastman was removed from the only remaining committee seat he held, on House Judiciary, over his opposition to a school funding bill.

[13] In May 2017, Eastman was involved in a controversy regarding his remarks suggesting that Alaska Native women in villages try to get pregnant on purpose to get a "free trip to the city" for abortion.

The suit alleged that his membership in the Oath Keepers and the group's role in the January 6 United States Capitol attack ran afoul of a disloyalty clause in the Alaskan Constitution.

The initial court ruling found that Eastman was not disqualified on First Amendment grounds because he did not himself actively participate in the Oath Keepers' attempt to overthrow the U.S.

"[26] Eastman traveled to Washington, D.C., on January 6, 2021, to protest the Electoral College vote count which confirmed Joe Biden's victory, and to see Trump speak at the "Stop the Steal" rally.

[28] On November 11, 2021, 69 local and other graduates of West Point wrote a letter published in Mat-Su Valley Frontiersman, Eastman's local paper, to demand that he resign from the legislature since, though he had stressed his military credentials and training at the United States Military Academy, he had dishonored the ideals of The Long Gray Line, that is, those who had matriculated at the USMA.