What's the toughest decision you've ever made as a coach?

On a road trip to a play-off game vs. a very good pass happy team, our best DB got caught with a can of chew (I'm a HS HC). Had to kick him off of the team and have the AD pick him up at our walk through. He had 9 pics in 9 games and was a a true LD DB.

We lost rather badly. But I'd make the same choice if it happened again.

Any time you have to fire a coach or kick a kid off the team is the toughest.

Fortunately I didn't have to do it very often.

I would do the same if it was against school/team policy. Absolutely hands down. What they do on their own time is their own decision, but it sounds like this player was caught either at a team function or on school grounds. 

Our coaches took us to an out of state passing camp my senior year, and we had to walk through metal detectors at the gates to get in  

Security didn't know what the hell was going once all of our skoal started setting them off and we just kept pulling cans and rolls of it out. 

Tough call but the right one.  Kid fought the law and the law won.  One thing I always tell my guys, you don't want to be a cautionary tale for the future players in this program.

At every school I've been at, tobacco has fit the same category in terms of the Code of Conduct as smoking or illegal drugs.  A first offense wouldn't result in a kid being totally kicked off, but it would be a minimum three game suspension.

Stepping away was the hardest thing to do for me.

I've never left to just leave, it was always work related or family related .

Leaving my last school, was really tough, I loved it there, I went through a period of what I imagine dexoting would be like.

geez man...kicked off the team for a can of chew?....funny how different consequences seem harsh depending on your circumstances. I remember several of us pulling out cans of cope at halftime in front of everybody and taking dips....nobody was fired up about it but everybody pretty much looked the other way
if it was drugs or booze or something I could see it, but chew seems a little tame to me....one man's opinion

I was a head coach at a school I really liked. I lived two blocks away, I had a great AD, an amazing staff to work with that genuinely enjoyed each other's company I had just finished my third year and we felt like we had made huge progress on rebuilding a traditionally losing program. Went from 1-9 the first year, to 3-6, to 5-5 with a few league wins and some close losses. We had an awesome Senior-to-be class, and the ones behind it were pretty good too. Investing in our youth program was starting to pay off, as it was improving as well...

Then my wife got the kind of job offer across the state that you just can't turn down. Incredibly hard decision. We both had good jobs. We wrestled with it, and it just turned out to be too good of a move for our family.

That team went 7-3 the next year and went to the playoffs in our classification (they'd been lower classification for a few years and gone to the playoffs) for the first time in as long as a bunch of people can remember. And I tip my cap to the guy that took over. He did a great job. I was happy to see them be successful.

The move turned out to be a great decision though. I landed as an OC at a pretty good school. Just finished my second year here and we made the state semis, losing to the state champ.

A mistake is packing your home uniform for an away game.  Throwing a football at your position coach and challenging him to a fight is a deep character flaw..  If you don't kick off a kid for that I have to wonder what it would take for a kid to get the boot. 

Putting in a freshman QB who had hardly played this year to start the second half of the National Championship game last night to replace the kid who got me there the year before. I feel kind of lucky that it worked out. But, then, I am a lucky guy and I make 10 million/year so I can afford to be bold sometimes.

Seeing your further responses I can see why you did it. All things in context make more sense.

Suspending some kids. Major distraction. No easy way out.

yeah...true that
I used to come unglued sometimes because there would be some dipstick that wanted to be captain butt chewer but was too much of a wuss to chew out the kids that actually needed chewing out, so he would wait till some good kid that he knew would take it messed up and then lay into them.......I was coaching O-line at the time so most of the guys I coached were solid....one of them pulls up a little before the finish line on an after practice sprint and the DB's coach wants to go off on him...all the while the starting cornerback is over there with his wang out helicoptering it at the cheer squad and nobody is gonna say crap