Interesting that a US based, self employed individual would be so honest as to request a 1099 form from a foreign based company. If ever there was an opportunity for him to get some “tax free” money, that would be it. Unless of course Freight Broker, you register and submit to the IRS yourself which would create a paper trail of payments for services rendered.
Not just self employed individuals but LLC carriers as well. I'm more concerned about running afoul of the IRS and therefore send all proprietorship and LLC carriers a 1099-NEC. Fines for omission or noncompliance tend to be astronomical, and they go up from there.
In 30+ years of operation, we have never been asked for such a form by any US carrier, large, small or otherwise. Other than being registered with FMCSA as a property broker, we have no reporting contact with the US government. While I admire your adherence to what might be the letter of the law, it would appear from what I read, that the requirement is only for US based payers of freight charges.
Most won't ask for it as they themselves aren't aware of the requirement or would prefer not to receive a 1099 as no 1099 means that they won't be reporting the income received. Somehow I don't think a Canadian based broker would get a pass.. every US carrier would prefer to work for Canadian brokers otherwise.