What was the highlight/most cherished memory of your military career?

Making sure an injured Iraqi child got medical attention that enabled her to walk again after being in the middle of a firefight.

Watching my son graduate from Marine Recruit Training 6 month after I retired from MCRD San Diego.

The brothers on my left and right that I got to work with every day. And flying Apaches. And blowing stuff up.

2001 I was deployed to Kosovo. While there I got to work with a Hungarian Infantry Bn. One day the CPT I worked with asked me if I'd ever driven a BTR-80, to which I replied no. He told me to meet him early Sunday morning which I did and got the run down and tour of a BTR-80, then I got to drive it. Was fantastic.
Then during the last part of the tour, the Hungarian Bn was changing out. I and other Americans were invited to attend the change of command ceremony. When we arrived I was approached by the Hungarian CSM and he asked me if I would present end of tour awards to some soldiers. He said I would be provided with a translator and I would present to an entire rank - all awards were lined up ready. I replied YES. As I went through I said a few words to every soldier. Later on at the reception for the outgoing and incoming CDRs, the outgoing CDR came to me with (my) translator and presented me with his personal coin. This coin will buy you more than a cup of coffee, it is one ounce of pure silver with the BN logo on front and denoting the KFOR deployment on the back.
I have briefed Commanding Generals, high ranking politicians. I've given courses to the Ministry of Defense General Staff (Ukraine), but being asked to present awards to soldiers from another country means more to me- I've received my share of medals, but this coin will always hold the top spot.

re-enlisting on the Bridge of No Return on the border between North and South Korea

In 32 years I have quite a few. If I had to pick one, I would pick something that happened during my last deployment. I had to coach, train, mentor and attempt to save a junior NCOs career- I was still an E7 at that time. I have always been part of a smaller shop or office and you don't really force shape. Had to figure out how to help a kid that had been misdiagnosed as being lazy when severe ADHD was the issue. Helped him with the healing process and got him the help he needed and the right agencies involved. Short story, he was vocally tuned in and could detail the job to me in great detail when asked, but when it came time to executing on his own he would get lost in details. Through correct intervention (not corrective action) we turned him from being on the verge of being kicked out to highly productive and motivated NCO. He was later diagnosed with a more challenging condition, but the original help and skills we helped him define made him successful. This is not something I consider a war hero type action, but it defined to me what my purpose had become and what my role was as a sneior NCO. It validated my career in an instant.

#1 was having my grandfather (retired Army Captain) administer my final oath of enlistment for my reinlistment after my deployment. I reinlisted in Sept of 2011 and he passed away the following July. I retired Dec of 2013. #2 (ranked by importance) was finally getting notification that I was on a list for deployment to Iraq (2010). I was finally going to actually SERVE my country instead of just training to do it. My rotation was 2nd to last I'm Balad. Our relief was the last rotation. We had already done a lot of closing down and downsizing to prepare for the pull-out. I was getting really scared that I would never realize my dream of deploying during wartime ops.

After 12 moths in Vietnam I was handed a manila envelope June 1970 inside which was a set of orders directing me to stand down from my current assignment and report to transient facilities Danang for transportation to Camp Butler Okinawa and further transportation to CONUS. Happiest day of my Military career.

Reforger 78, my track commander on my M-113 wanted to drive for a bit. I jumped in the commanders seat. It seems he left his M-16 lay on top of the vehicle and I did not notice, and it was thrown over. We realized it when we got to the next town. We went back, in the dark, and found it. That was a major HOLY SHIT moment for both of us, that ended up a lot better than it could have.

After thinking some more I would change my previous answer. The highlight was when I check mail for the first time after arriving back in the USA, I got a letter saying I was accepted to complete a degree in civil engineering and would become a cartographic officer.

then I went to the library to find out what that was.