Born in Toronto

Summers in Muskoka where at age 9 I met my future wife Bonnie
She was ready to get married.
I was not there yet.

Learned to waterski and fished almost everyday with my uncle Sam.
I drove the boat.

I taught waterskiing at 3 summer camps in my teens.
Many of these campers still remember how much fun they had learning to waterski.

During high school, I was on the swim team and chess club at Bathurst Heights Secondary School.

In 1967 I was an Ontario scholar and was accepted into medical school at U of T

In 1973 I graduated from medical school and opened my family practice.

1973- 1980 worked in 4 ERs working day and night seeing thousands of patients
Gained incredible experience.

1976 my daughter at age 18 months was admitted to Sick Kids with sepsis.
She almost died but I advocated for her. She survived a ruptured appendix.
This taught me the importance of patient advocacy and changed my approach to practicing medicine.

1978 took cooking classes and re-met Bonnie Stern. I was ready to get married this time.

1980 curled at the OMA bonspiel in Nickel City and won a silver cup.

1985 graduated from the Rotman business school

1985-1991 worked in healthcare finance at 2 boutique merchant banks and edited two books on investment banking. One book in Canada. Another book in the USA.

1995 started Rupert Case Management to do complex case management and evolve this advanced model of care seen by many as disruptive. No one understood case management. Many still don’t understand.

1995-2020 have completed thousands of assignments helping complex clients throughout Canada while creating a global ecosystem of over 3,000 world class experts to provide virtual case reviews for clients located anywhere

2015-2018 was the addiction doctor at a residential addiction centre having provided care to hundreds of clients

2016 partnered with pharmacists in smaller communities to provide travel health advice to clients using telehealth

2016-2020 investigated by the College of Physicians and Surgeons of Ontario for my work in addiction and in providing travel health advice using telehealth. A challenging exercise during which my own advocacy could not resolve the issues. The investigator at the College was fired during this experience for traumatizing me during this process.

Feb 2020 retired from family practice after 40+ years with lots of hugs from my patients who really appreciated the help over many years

May 2020 gave up my medical license to practice in Ontario.

May 2020 refocused all my efforts on expanding my work in patient advocacy and to continue to be a disruptor in the medical system