“I'm going to fail height-weight on purpose and get booted” – how would you handle this?

I know someone who may do just that. Myself and a few others are trying to convince them otherwise. As I understand there was once a time where you could get an Admin Sep for Height and Weight and it would still be Honorable. As of right now it's a General Discharge. Knowing that I'm trying to get them to understand that if they want out they should leave with an Honorable Discharge and then walk away.

I would say try and convince them, make sure if they are aware of the consequences of doing so. They need to understand their options. So a sit down with their SGT and 1SG and maybe the XO or CO. If that's not an option and they're dead set on it... Make the separation as quickly and painlessly as possible.

I'm going to respond only because I was there once. I was to the point were poison leadership and family issues had me ready to say "to hell with it." I would fall out of runs, became a sick call regular, and in general let myself go to hell. I was done with the Army and I only wanted to be somewhere else. My leadership was nothing but poison from the ground up. Rather than trying to address and help with my issues, my leadership compounded the problem by piling on even more stress. I'm not going to get into what started my decent, but it started when a member of my leadership decided throw me under the bus to save his own butt. He did it because of the same poison leadership, so I can't really blame him.
Leaders need to step back, take a good look at themselves and if they don't see a problem, then they are the problem.
To these people saying "He needs to tow the line or UCMJ action!", that is poison leadership.
This solider came to you, told you his plan. He's asking for help. He's a member of the mafia, so it isn't going to be easy for you. He's knows enough to play the game, he just doesn't know all the moves yet. If he's married, start there.
My situation turned out well for me, I was fortunate that I had a 1SG I could talk to and explain the problem, who was interested in hearing the problem and genuinely wanted to help. The thing is, that 1SG wasn't my 1SG. I finished up my contract and 10 years more.
I'm out now, been out for awhile. I can approach this from a very non military point of view The very best advice I can give that solider is this,
Tough it out, civilian life isn't exactly what he remembers it. An honorable discharge equals free health care, home loans, GI Bill, VR&E, as well other benefits. All of which are impossible to obtain with a dishonorable discharge. I've had considerably more need to produce a DD214 than my degree. These things seem trivial, but the cost does add up. He won't see it now, but in 5 years, he'll be glad he did. As a OIF veteran, he's going to need the VA for healthcare, trust me!
Sir, my advice to you is this, attempt to get to the bottom of the problem and help. You're obviously concerned or you wouldn't have posted. Do what you can, but remember you have a battery full of other soldiers that have "bumps and bruises" also. If the solider just isn't receptive, then cut your loss. No point in holding him, get him off your TO&E and let him learn one of lifes hard lessons.

Now that you've read mine and others assessment, how did you handle the situation?

If the SM has been in long enough (2-3 years?) and has performed well enough to make it to E-4 something happened to make him lose his mojo. High op-tempo, bad leadership, Jody is taking care of his sweetheart back home, something. Find the tipping point, concentrate on helping him get over it, and you may be able to bring him back from the dark side with some good old fashioned leadership along with a healthy PT program.
If not, explain that his attitude and demeanor in the coming months will make a big difference in how his life will be lived. If he wants to become a cancer to the unit morale it will be dealt with swiftly and severly. If he is intentionally becoming obese to expedite his end of service he doesn't deserve the rank he is wearing. Liberty is optional. If his waist line is increasing, the tailor shop will be accepting a large portion of his money to ensure uniforms still fit.
Make him choose between sucking it up for however longer he has until EAS/ETS and a miserable existence for almost the same amount of time. That may be all the motivation needed.

There was a Soldier in my platoon that did this in 1991, but he was also helped by clintons "who wants out of the Army" program.
This kid gained about 75 pounds so fast his uniforms became almost skin tight.
He was processed out of the Army.

Do everything you can to help this person get out as quickly and smoothly as possible. The exact opposite of what you should be doing if someone has a profile and is working to get back withing height/weight standards.

On a side note, the crooked tape in the picture annoys me. If your going to measure something, make sure your measuring it correctly.

I am of a conflicted mind on this one. While there is an unhappy person who has found an easy out do we hold them to a standard or do we say Bye and free up resources?

On the one hand you have a member that had publicly stated they are not even going to try, They don't care. What does that say to the rest of the command if they are given a free pass? What does that tell the new Junior Enlisted? I would want to beat them every day till they were in standards to prove the point, you signed on the line. this isn't the cub scouts you don't get to just go home when your unhappy.

On the other side of that, is why would I want to keep someone that will be bringing down moral, is a risk to others and the mission, and quite frankly a drain on resources. Why keep paying someone and giving them all these benefits when they refuse to follow the rules and regulations?

The only way I can coincide these two thoughts is a public mast for dereliction of duty and a other than honorable. Make it public so everyone knows there are consequences for their choices and actions.

All of this is based on your (1) and (2) statement.

CPT Aaron Kletzing I would talk to the Soldier about health effects of being overweight, why is he/she taking this coa etc, and if he/she insists on getting fat I would gladly process the necessary paperwork to include the flag(no passes/leave during that time), put him/her in the extra pt that no one else has to do, and give him/her as a parting gift a bk gift card and a nice kick in the behind.

CPT Aaron Kletzing He would have been gone as fast as i could get rid of him.He would be detrimental to morale .

He was not drafted. He needs to Man up and do his job. That's the problem now days. Everybody want something but doesn't want to work for it. He was a Sorry person before he joined.

Oh man why. Your young you think 2 to 3 years is so long. Its not. Finish your time. Get an honorable discharge. Life afterward will be so much better. I thought i hated the Army for the first year and a half. Then i realized why i didnt want to make a career out of ut it was ok. Good people and i learned valuable life lessons. I urge you to rethink this. Life is long and a mistake at your age could affect your long term chances.