Cracraft was born in Rancho Santa Margarita, California, and grew up in nearby Trabuco Canyon.

He attended Santa Margarita Catholic High School, where he played football and baseball and ran track.

He was named All-State, All-CIF and All-Trinity League as a junior after recording 46 receptions for 654 yards and six touchdowns for the Eagles.

The next year, Cracraft caught 66 passes for 771 yards and eight touchdowns despite missing three games to a stress fracture in his foot.

[9] Cracraft entered his junior season on the 2015 Fred Biletnikoff Award watchlist, but missed three games due to a stress fracture in his opposite foot and finished the year with 53 receptions for 615 yards and four touchdowns.

[10] He returned from his injury to play in the 2015 Sun Bowl and caught five passes for 63 yards in the Cougars' 20-14 win over the Miami Hurricanes.

2 in school history behind teammate Gabe Marks), 2,701 receiving yards (6th) and 20 touchdowns (6th) in 42 games played while at Washington State.

[13] Due to his knee injury, Cracraft was unable to participate in the pre-draft process and ultimately went unselected in the 2017 NFL draft and was not initially signed by any team as an undrafted free agent.

He worked out for the New England Patriots in September 2017 following a season-ending injury to Julian Edelman, but was not offered a contract by the team.

[17][18] Cracraft was signed to the Broncos' practice squad after being cut from the team's active roster at the end of the 2018 preseason.

[20][21] He caught his first career pass, a 44-yard reception, on December 30, 2018, during the Broncos final game of the season against the Los Angeles Chargers.

Cracraft's older brother, Skyler, walked on to the Cougars as a safety after River committed to the team despite not having played organized football since high school two years prior.