Link it to the Sched C  then enter an offsetting expense for same amount  with explanation income is stock options being reported on Schedule D       Then proceed with your Sch D/8949

Ignore this - I obviously didnt know how this should be reported  - sorry

But, you don't pay SS/Medicare on stock options, right? If I only used his cost basis as the expenses, he would have to pay those taxes on his profit. That doesn't seem right.

Think this would be okay and not raise a red flag?

Maybe it should have been on a W2 then it would flow through as federal taxable but not subject to SE taxes

link the 1099NEC to Other Income line    - client would pay tax as required  but no SE tax

But he was never an employee for the company. Everything I've read on the IRS pubs stated it should have been reported on the 1099-NEC, but it doesn't tell me how to report that on his return. The amount on his 1099-NEC is the proceeds from the stock options which I need to report on D/8949.

So then don't write the full amount off in the Sch C as you stated before? Oh my goodness this is so confusing. 

Right - I agree that he has to pay taxes on the value of the profits. But he has a huge carryforward of loss from previous stocks. We were hoping to be able to offset the stock options with these losses. So, would it be okay for me to use stock options expenses on the Sch. C. and then report the sale on the Schedule D showing the profit? Then his long-term losses would offset the profit?

The options he received, exercised and sold are taxable compensation equal to the excess of the value over the amount he paid for them, if anything..

I don't see why it wouldn't be subject to SE tax. If he was an employee it would be W-2 compensation subject to SS & Medicare tax.

His capital gain or loss equals the sale price minus the taxable compensation minus what he paid.

But he was never an employee so it's not the same, right? Could I report it as Sch C., then 100% expense stating as reported on Sch. D. Then, report the full amount as profit on the 8949/Sch. D? He has a huge carry forward loss in capital gains which would help offset the profit. 

Or no, this isnt the way?

His director fees were subject to SE tax. This is part of his director compensation.

There is no expense to put on Sch C.

Schedule D will have a small gain or loss.

So these stock options have to be reported on sch c with 100% subject to FICA???

As far as  I know, yes.

what did the W2 look like?  Were they subject to SS/Mdcr on the W2?

Is this what you need:

https://www.irs.gov/taxtopics/tc427

Obviously we don't have any details so we can't "do the math" on this.  But I completely agree with this line of thinking.  The directors fees were subject to SE tax, this is just a different form of compensation so it should also be subject to SE tax.

In my career I've seen enough equity compensation screwed up that I don't take anyone's word for it.  Get the documents, follow the math.  Look at each transaction.  Options were granted, how many what strike price?  Options were exercised, were there broker fees, was this cashless or did he pay the strike price?  Stock was sold, was it a same-day sale, were there broker fees?  Follow your share counts through the process.

I had read this, but it reads to me as if he was an employee, which he was not.

No, but they reversed the w2 when they realized he was not an employee.

So I get the part for schedule D. What do I link the $282k from the 1099-nec to? To sch. C w/ all the amount taxable for Fica/fed/state or to Other Income,

I'd do Sch C.

Crap. My client is not going to be happy at all. 

Have a tax client with same situation but was an employee, some added to W2 and received the final shares on a 1099nec.

Did you report on Sch C with SE tax and then use the schedule D?