Growing up in the Cincinnati Ohio area, he is an Eagle Scout in addition to being a standout prep dual threat quarterback. Over his four-year career, he rushed for 6,666 yards and 91 touchdowns. In 2015, he was named the Division III Ohio Player of the Year as well as the Southwest District Offensive Player of the Year. His senior season rushing total of 2,707 was good enough for the 21st best single season performance in Ohio high school history. He posted seven 200-yard games and three 300-yard games, including one 373 yard performance.
Recruiting
Despite a record-breaking high school career, Montgomery was only lightly recruited to continue his football career in college. He was only recruited by Miami, Ball State, Buffalo, and Iowa State. He eventually committed to the Cyclones.
Montgomery's break out season was in 2017. He led the Cyclones in rushing yards and yards from scrimmage with 1,095 and 1,383 respectively. He finished second in the Big 12 in rushing yards and touchdowns behind only Justice Hill. Montgomery led the nation in forced missed tackles with 104, breaking the previous record of 89 set by Dalvin Cook. Against Iowa he ran for 113 yards, rushed for a touchdown, and had 53 yards on receptions. In an upset win at #3 Oklahoma, Montgomery ran for 55 yards and a touchdown and caught 7 passes for 89 yards. He had a career day against Texas Tech rushing for 164 yards on 28 attempts, averaging 5.9 yards per play. Montgomery had a three straight 100 yard performances against West Virginia, Oklahoma State, and Baylor with 115, 105, and 144 yards respectively including three touchdowns against the Cowboys. Montgomery received multiple accolades at the end of the regular season. He was named a first-team All-American by Pro Football Focus as well as consensus first-team All-Big 12.
2018 season
Montgomery started the season slow, but had a string of four straight 100-yard games with five touchdowns from mid-September to mid-October, and ended the season with another string of three straight 100-yard games with six touchdowns, including 179 yards from scrimmage in the 2018 Alamo Bowl loss to Washington St. Montgomery finished the 2018 season with 1,216 rushing yards and 13 rushing touchdowns.
College statistics
Professional career
On January 7, 2019, Montgomery announced that he would forgo his final season of eligibility and declare for the 2019 NFL Draft. The Chicago Bears drafted Montgomery in the third round with the 73rd overall pick in the draft. Montgomery signed a four-year rookie contract with the team on June 14.
2019 season
Montgomery made his NFL debut with the Chicago Bears in Week 1 against the Green Bay Packers. In the game, Montgomery rushed for 18 yards on six attempts and caught one pass for 27 yards as the Bears lost 10–3. In Week 2 against the Denver Broncos, Montgomery rushed 18 times for 62 yards and his first career NFL touchdown as the Bears won 16–14. Though utilized more than veteran Tarik Cohen, Montgomery failed to reach 70 yards in any of the Bears' first seven games. After 11 carries for 25 yards in Week 6 and a disastrous two rushes for six yards and a fumble in Week 7 against the New Orleans Saints, Montgomery responded in Week 8 against the Los Angeles Chargers with 27 rushes for an NFL-second best 135 yards and a touchdown in the 17–16 loss. In Week 9 against the Philadelphia Eagles, Montgomery rushed 14 times for 40 yards and two touchdowns in the 22–14 loss. This was Montgomery's first game with multiple rushing touchdowns of his career. In Week 17 against the Minnesota Vikings, Montgomery rushed 23 times for 113 yards and a touchdown during the 21–19 win. Overall, Montgomery finished his rookie season with 889 rushing yards and six rushing touchdowns.
Personal life
Montgomery had a difficult childhood. He does not know his father, and his mother moved the family numerous times around Cincinnati due to economic hardship. He remembers using the oven for heat, and boiling water collected from gas stations in the bath tub when either was disconnected. He has a brother who was incarcerated for drug trafficking and murder. After scoring a touchdown, Montgomery frequently holds up a "V"-sign in memory of a high school teammate and role model who was murdered during a home invasion.
