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Thomas Kaʻauwai Kaulukukui, Jr. was born in Honolulu, Hawai'i in 1945. He graduated from Kamehameha High School, which at that time was a military institute. He then graduated from Michigan State University in East Lansing, Michigan in 1967, obtaining a Bachelor of Science Degree in Health, Physical Education, and Recreation. He married, and then taught physical education in Michigan.  

In 1968, he was drafted into the United States Army, where he quickly rose to the rank of Staff Sergeant (E-6). In 1969-70, he fought in Vietnam as a platoon sergeant in the airborne infantry, leading a platoon of men in the 173d Airborne Brigade. In 1970, he was honorably discharged, and was decorated by both the United States and the Republic of Vietnam.

After completing his military service, he returned to graduate school for a year at Michigan State University, working on a Master's Degree in physical education, specializing in exercise physiology. From 1971 to 1974, he was a public school teacher in the Department of Education, State of Hawaiʻi. He taught physical education at Kailua High School, where he served as the head wrestling coach and assistant football coach. He later taught English at Samuel Wilder King Intermediate School in Kaneohe, Hawaiʻi. 

In 1974, he entered the William S. Richardson School of Law, University of Hawaiʻi. He graduated from law school in 1977 and was admitted to the Bar of the State of Hawaiʻi in 1977. He was then selected from a national pool of applicants to be law clerk to Chief Judge Samuel P. King of the United States District Court for the District of Hawaiʻi. He is qualified and has been admitted to practice law before all Hawaii state and federal courts, as well as the 9th Circuit Court of Appeals and the United States Supreme Court. 

In 1978, he entered the private practice of law, and handled a wide variety of civil cases before the state and federal courts, and before state and federal administrative agencies. His law practice emphasized litigation and litigation matters, but he also has substantial experience in matters involving business and commercial planning, counseling, and negotiation.

In 1988, he was appointed by Governor John D. Waiheʻe, to be a trial judge of the First Circuit Court in Honolulu, Hawaiʻi. He presided over criminal trials, criminal motions, civil trials and civil motions. He served as the Arbitration Judge, and as the Land Court, Tax Appeal and Administrative Appeals Judge. He has also served the Judiciary, the local Bar and the public as a chairperson and member of several committees.  He was a member of the Executive Committee of the Hawaiʻi State Trial Judges Association. He conceived, organized and headed the Court Security Committee, to improve awareness of security issues among judges and their staff.

In 1993, he relinquished his judgeship to work to improve the health of the people of Hawaiʻi, and especially Hawaiian people. He became the Vice President, Community Affairs, for The Queen's Health Systems (“QHS”). The Queen's Health Systems is a family of health care companies, with over 4,000 employees in the State of Hawaiʻi. The best-known of these companies are The Queen's Medical Center and Queen Emma Foundation. In his work at QHS, he worked to improve community health through a variety of programs, such as preventive health, education, housing, youth leadership, and Hawaiian culture.

In 1995, he was appointed by Governor Benjamin Cayetano to be an Oahu Commissioner on the Hawaiian Homes Commission, a position he held for nearly four years. 

He also served as a board member of the March of Dimes (prevention of birth defects); Pacific Islanders in Communication (film-making by Pacific Islanders); Family Treatment Center (adolescent mental health); Winners at Work (vocational education for the disabled); Pacific American Foundation (Pacific Islander leadership); Advisory Committee for Minority Veterans (Veterans Administration); and Vietnam Veterans Leadership Program (Veterans Affairs).

In 1998, he was appointed a Trustee of the Liliʻuokalani Trust, which was formed by Hawaiʻi’s last queen to care for orphan and destitute Hawaiian children. He served as Chairman of the Board from 2002 through 2017. He still serves on the Board of Trustees. He also serves as a mediator and arbitrator, assisting persons and organizations by resolving disputes.

Judge Kaulukukui is a capable orator, as well as an active teacher of leadership who has given and continues to give numerous leadership speeches, seminars, and other educational presentations. He stresses maximizing personal potential through the application of ancient and traditional leadership principles and practices, and their relevance to modern leadership.

A seeker of knowledge, he has studied many disciplines and activities in his quest to achieve a balanced, harmonious and productive life. This includes reading; studying Hawaiian culture and language; leadership development; philosophy; writing short stories, essays, and poetry; music; oratory; woodworking; and tinkering with and collecting vintage cars and guitars.  He is currently challenging himself by studying Hawaiian slack-key guitar, a unique form of finger-picking guitar-playing.

He is a long-time student and teacher of martial arts, having attained the rank of third-degree black belt in Tae Kwon Do, seventh degree black belt in Aikido, and the teaching rank of olohe in the Hawaiian martial art of Lua. He has lived in Hawaiʻi, the Midwest, the southern U.S., and Southeast Asia. He has traveled in or through nearly every state of America, parts of Canada, Japan, Germany, Sweden, and some islands of the South Pacific, including Samoa, Tahiti, Aotearoa (New Zealand) and the Marquesas Islands. He and his wife, Joyce, have been married since 1967, and reside on the island of Oahu. They have 3 children, 9 grandsons, and 2 large happy dogs.