James A Dailey, Jr., who is the middle child of James Sr. and Diane Dailey, was born May 30,1961 in Salem, Ohio, and grew up in Columbiana, Ohio, which is the home of Harvey S. Firestone of Firestone Tire fame. Dailey attended Columbiana High School where he was a two-year letterman in football, and a three-year letterman in wrestling and baseball. He continued wrestling for a very short time at Youngstown State University and graduated with a bachelor's degree in elementary education in 1984.

After graduation, he taught math at various schools in Ohio and Florida and continues to teach to this day. He began his coaching career at his alma mater, Columbiana, in 1980, while attending college. He coached junior high football and wrestling until 1985, when he was awarded the head wrestling position at his high school, a position he held until 1987.

In 1988 he headed south to the Sunshine State where he accepted a temporary position to teach and coach football and wrestling at Fort Pierce Westwood High School. The following year he found himself back in Ohio as the head wrestling coach while also teaching and coaching football at Salem City Schools.  

Dailey moved to Austintown Fitch High School as an assistant wrestling coach for longtime friend Brett Powell, a Lifetime Service to Wrestling recipient from the Ohio Chapter of the National Wrestling Hall of Fame. He returned to Florida to teach and be the head wrestling coach at Port St. Lucie High School from 1995-2013.

After taking a short break from coaching, he became the head wrestling coach at South Fork High School from 2019-21.

Dailey coached several club programs, both AAU and USA Wrestling, in Ohio and Florida. He traveled to the Dominican Republic in the early 2000s as part of International Sports Services. Dailey was the coordinator of wrestling for ISS, which brought wrestlers from the United States to compete with wrestlers from the Dominican Republic. It was during his time with ISS that he met Jose Helena, a Lifetime Service recipient from the Georgia Chapter of the National Wrestling Hall of Fame.

Dailey was always involved in wrestling since grade school, participating, coaching, and even officiating. He got his start in officiating in Ohio in the Steel Valley Wrestling Officials Association from 1991-94, and continued in Florida until 2023 with the Treasure Coast Officials Association. 

He was fortunate to accumulate 200 wins during his coaching career while also coaching three state champions in Florida and one in Ohio. Dailey coached 36 state place-winners and had 68 state qualifiers and six district titles. He led his teams in Florida to three Top 10 finishes and his teams in Ohio to one Top 10 finish.

Dailey was Columbiana Coach of the Year in 1987 and three times was named Treasure Coast All-Area Coach of the Year.

He currently teaches math at For the Love of Learning private school, continuing his involvement in education that began in 1984.