Sergeant Major Wesolowski enlisted in the United States Marine Corps on 6 August 1996. He attended recruit training at Marine Corps Recruit Depot, Parris Island, South Carolina. Upon graduation, he attended the United States Army Military Police School, Marine Corps Detachment at Aniston Alabama, graduated in July 1997, and was awarded the Gung Ho Award. He reported to Military Police Company Bravo Headquarters and Service Battalion Fourth Service and Support Group in July 1997 and was promoted to Lance Corporal on 1 September 1997. He was awarded Marine of the Year for Military Police Company Bravo for the year 2000. On 1 January 2001, he was promoted to Corporal.
Sergeant Major Wesolowski was selected Non-Commission Officer of the Third Quarter 2001 for Headquarters and Service Battalion Fourth Force Service and Support Group. He was awarded Non-Commission Officer of the Year 2001 for Military Police Company Bravo and meritoriously promoted to Sergeant on 2 November 2001.
On 3 January 2003 Sergeant Major Wesolowski was activated in support of Operation Iraqi Freedom. Sergeant Major Wesolowski deployed to Iraq and participated in combat operations attached to Combat Service and Support Battalion 10 / Combat Service and Support Battalion 11 First Marine Division. He was meritoriously promoted to Staff Sergeant on 2 April 2004.
In June 2004, Sergeant Major Wesolowski was again activated in support of Operation Iraqi Freedom 2. He was attached to Regimental Combat Team 7, First Marine Division. He participated in combat operations in and around the city of Fallujah Iraq. Upon returning from Iraq he served as Military Police Company Bravo’s Company Gunnery Sergeant. He was promoted to Gunnery Sergeant on 1 November, 2007.
Sergeant Major Wesolowski continued to serve as Company Gunnery Sergeant for Military Police Company Bravo until December 2009 when he was activated in support of Operation Enduring Freedom. While in Afghanistan he held the billet of Platoon Sergeant/ SNCOIC of a Police Mentor Team for 1st Battalion, 2nd Marines. He participated in combat operations in and around the city of Musa Qua'eh. Sergeant Major Wesolowski served as Military Police Company Bravo’s Company 1stSgt from 1 May, 2011 until his promotion to 1stSgt on 1 September 2012.
Sergeant Major Wesolowski served as Company First Sergeant for Kilo Company 3rd Battalion, 25th Marines, 4TH Marine Division, from 1 September 2012 to 15 May 2016. While at Kilo Company Sergeant Major Wesolowski participated in OCONUS exercises in the Baltic states of Estonia and Lithuania, as well as Mountain Exercise 3-13, Bridgeport CA and Infantry Training Exercise 4-15, 29 Palms CA.
In May 2016 Sergeant Major Wesolowski was promoted to his current rank. Sergeant Major Wesolowski has been serving as the Squadron Sergeant Major, for Marine Tactical Air Control Squadron-48 since September 2016.
Personal awards include: Navy and Marine Corps Commendation Medal with two Gold Stars, Navy Marine Corps Achievement Medal with one Gold Star and Combat Action Ribbon with one Gold Star.
As a civilian Sergeant Major Wesolowski has earned Bachelors and Masters Degrees in Criminology from Indiana University of Pennsylvania. He also holds Police Officer Certifications in the states of Pennsylvania and Maryland. He is law enforcement professional with 17 years experience as a probation officer, as well as 2-year experience as a police officer. Sergeant Major Wesolowski is currently is a probation officer, assigned to the Special Services Unit, with the Allegheny County PA Department of Probation.