[2] He received his undergraduate degree (with high distinction) from Pennsylvania State University, where he ran varsity track and cross-country under coach Harry Groves.

[4] He completed internal medicine residency at Christiana Care Health System and infectious diseases fellowship at Oschner Foundation Hospital.

Winslow began his in medical private practice in Wilmington, Delaware where he started the state’s first multidisciplinary clinic for HIV patients in 1985.

In 1988 he joined the DuPont Company where he worked both as a bench scientist on HIV drug resistance then later designed the clinical trials supporting FDA approval of efavirenz.

In 1999 he became Vice President of Regulatory Affairs at Visible Genetics Inc. and led the FDA clearance of the TRUGENE HIV-1 drug resistance test.

He is a member of the IDSA Sepsis Task Force, and previously served as Chair of the Standards and Practice Guidelines Committee.

Winslow deployed to the Middle East six times from 2003 to 2011 as a flight surgeon supporting combat operations in Iraq and Afghanistan.

From January–April 2003, Winslow was the flight surgeon responsible for combat rescue operations from Tikrit to northern Iraq during the initial invasion.

[11][12] He and his wife, Dr. Julie Parsonnet, used the $1 million settlement to form The Eagle Fund, a charitable trust which provides aid to Middle Eastern and Central American refugees.

Donations to date have included United States Fund for UNICEF, International Rescue Committee, Inc., Save the Children, Crisis Action, Inc., Oxfam, Global AIDS Interfaith Alliance, Episcopal Relief and Development, Asylum Access, Sana Relief Fund of Lucille Packard Foundation for Children's Health, American Near East Refugee Aid, Jesuit Refugee Service USA, UNRWA USA National Committee, Iraqi Children Foundation, UNHCR, and Cristosal.

During his November 2017 Senate Armed Services confirmation hearing, Winslow was asked about the Sutherland Springs church shooting that had occurred two days prior.

[21][22] From November 2021 until July 2022, Winslow served as senior CDC advisor to Operation Allies Welcome, a DHS effort to support and resettle vulnerable Afghans, including those who assisted US forces in Afghanistan.

[30] Winslow soloed in a glider at age 14 and holds an Airline Transport Pilot license and type ratings in the Boeing 737, Douglas DC-3, the L-29 Delfin, and L-39 Albatross jets.