Healey played professional football as a tackle in the NFL for the Rock Island Independents from 1920 to 1922 and for the Chicago Bears from 1922 to 1927.

Halas indicated that he had been blocking against Healey and did "just a wee bit of holding" in order to spring star halfback and Bears co-owner Dutch Sternaman for a 7 yard gain.

It's a darned good thing I did, by golly, for Healy's fist whizzed past my nose so fast it buried itself up to the wrist in the ground.

[12] Healey would play the last 3 games of the 1922 season with the Bears and would remain with the team for an additional five years,[13] earning induction into the Pro Football Hall of Fame in 1964.

[15] This entertaining story, told by Halas decades after the fact, is contradicted by reporting in the Rock Island Argus at the time of the deal, however.

[16] Bears co-owner Dutch Sternaman got wind of the free player loan and stepped in to offer Independents owner Flanagan $100 for use of the Healey for the duration of the year.

[13] Healey later recalled his pleasure at joining a team with superior facilities: "At Rock Island, we had no showers and seldom a trainer.

[17][19] In 1925, he was the only player to be selected as a first-team All Pro by Collyers Eye magazine, the Green Bay Press-Gazette, and Joseph Carr.

[24] After retiring from football, Healey and his wife lived in South Bend, Indiana, where he worked as a salesman and later sales manager for France Stone Company.

Interviewed in 1949, Healey opined that, with the development of the platoon system, modern linemen were "something akin to sissies" and added, "In the old days we used to go on the field prepared for 60 minutes of work and nothing short of a broken leg, arm, or ankle could get us out of there.

Healey died three years later in December 1978 at age 83 from multiple causes, including malnutrition, cardiac and pulmonary failure, and cancer of the stomach and lung.