Brigadier General Winnacker attended the University of California, Santa Barbara and concurrently completed the PLC, Ground program. Upon receiving a BA in history, he was commissioned a Second Lieutenant in June 1997.
Upon completion of The Basic School, Lieutenant Winnacker was selected for meritorious augmentation and attended the Infantry Officers Course. He was subsequently assigned to Fox Co, 2d Bn, 5th Marines in 1998. With F 2/5 he served as the scout swimmer platoon commander and completed a 31st MEU deployment. Upon returning from deployment, he was frocked to Captain and assigned as the CO of HQCO 5th Marines. In 2001, he resigned his regular commission and joined Echo Co, 2d Bn, 23d Marines in a reserve capacity.
In 2002 2/23 was mobilized in support of Operation Noble Eagle and deployed to Camp Pendleton. In early 2003, the mobilization was extended and 2/23 was attached to 1st Marines for OIF I. Following the March Up, 2/23 returned to CONUS and Capt Winnacker served as the 5th Marines S-4 before demobilizing and returning to a reserve status.
From 2004-2006, Capt Winnacker served as the XO of E 2/23 before transferring to 4th Force Reconnaissance. During this period he completed AWS (DEP). Following promotion, Maj Winnacker served as the P/WST OIC at 4th Force from 2007-2009 while completing the EWS seminar. From 2009-2011 he served as the S-3 and subsequently XO while mobilized as the command element of SPMAGTF-Africa. Upon demobilization, Maj Winnacker served in the 4th MARDIV G-3/5 as an exercise planner from 2014-2016. He was promoted to Lieutenant Colonel during this period.
In 2014, LtCol Winnacker assumed command of 4th Force Reconnaissance Company and remained in this role through 2016. He completed Air War College (DEP) during this period. Following this command tour, he transferred to MARFORPAC as a senior watch officer and exercise planner in the G-3. In 2017, he transferred to 23D Marines as the regimental XO and remained in this role until promotion to Colonel and command selection as the Senior Reserve Advisor, 23d Marines in 2019. Col Winnacker remained in this role through 2022 to include deployment in support of Operation Allies Welcome at Fort Pickett, VA. During this period he completed Joint Combined Warfare School-Hybrid.
In 2022 Col Winnacker transferred to Marine Innovation Unit to serve as Chief of Staff. He remained in this billet until transferring to the Force Headquarters Group G-7 in 2024.
On 6 June 2025, Brigadier General Winnacker promoted to his current rank and assumed the duties of Commanding General, Force Headquarters Group, Marine Forces Reserve.