Upon graduating from college in 1920, Henry was 5 feet, 11 inches and weighed 235 pounds, but was "considered a fast man, able to do the hundred in close to 11 seconds." He received offers to play professional football for the Canton Bulldogs, Cleveland Tigers, Akron Pros, Hammond Pros, and Rock Island Independents. He signed with Canton in September 1920, saying he wished to play with Jim Thorpe.
As a rookie, Henry participated in the first season of the new professional association that became the NFL. He played all 13 games for the 1920 Bulldogs team that compiled a 7–4–2 record. At the end of the 1920 season, Henry was selected as a first-team tackle on the All-Pro team selected by sportswriters Bruce Copeland (Rock Island Argus).
In 1921, Henry again played every game for the Bulldogs team that compiled an 8–3–3 record. Henry was selected as a first-team All-Pro team compiled by the Buffalo Evening News.
In 1922, Guy Chamberlin joined the Canton team as player, coach, and part owner and built the Bulldogs into one of the NFL's first powerhouse teams. The 1922 Bulldogs team included Pro Football Hall of Famers (Henry, Chamberlin, and Link Lyman), compiled a 10–0–2 record, shut out nine of twelve opponents, outscored all opponents 184 to 15, and won the 1922 NFL championship.
The following year, the 1923 Canton Bulldogs with Henry and Chamberlin compiled another undefeated season (11–0–1), shut out eight of twelve opponents, outscored all opponents by a combined total of 246 to 19, and won its second consecutive NFL championship. Henry led the 1923 team with 58 points on nine field goals, 25 extra points, and a touchdown reception. On October 23, 1923, he set an NFL record with a 94-yard punt; his record stood until 1969. On November 11, 1923, with the Bulldogs trailing to Buffalo by a 3–0 score and a half minute left in the game, Henry blocked a Tommy Hughitt punt and then drop-kicked a field goal to preserve Canton's undefeated season. At the end of the 1923 season, Henry was selected by Collyer's Eye magazine, the Green Bay Press-Gazette, and the Canton Daily News as a first-team player on the 1923 All-Pro Team.
In August 1924, Cleveland jeweler Samuel Deutsch bought the Canton Bulldogs and moved the team to Cleveland where they became the Cleveland Bulldogs during the 1924 NFL season. Henry did not join the Bulldogs in Cleveland, instead playing for the 1924 Pottsville Maroons of the Anthracite League. Henry led Pottsville to a 12–1–1 record and the Anthracite League championship and was named to the All-Anthracite team at the end of the 1924 season.
In January 1925, Henry was reinstated to good standing with the NFL, having been subjected to sanctions the previous year when he refused to join the Bulldogs when the team moved to Cleveland. In the summer of 1925, Henry and four other Canton alumni (Link Lyman, Rudy Comstock, Ben Jones, and Harry Robb) bought the Cleveland Bulldogs for $3,500 and moved the team back to Canton. Henry appeared in only six games for the 1925 Canton team, missing much of the season due to injury. The following year, he appeared in all 13 games and served as co-head coach with Harry Robb of the 1926 Canton team that compiled a 1–9–3 record.
Before the 1927 season, the NFL dropped 12 teams, including Canton. In September 1927, Henry signed to play with the New York Giants. He appeared in only four games for the Giants. In mid-October 1927, he was acquired by the Pottsville Maroons (for whom he had played in 1924) in a transaction with the Giants. He remained with Pottsville through the 1928 season. He also served as head coach of the 1928 Pottsville team that compiled a 2–8 record against NFL opponents.
In 1929, Henry returned to Washington & Jefferson as an assistant football coach. He became athletic director in 1932 and held that position until his death in 1952. He was also the head coach of the Washington & Jefferson football team in 1942 and 1945.
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