He could be feasibly trapped if he wanted to leave, but that would depend on whether you have any non-restrictive covenants within your role. My recent situation might be worthwhile taking into consideration:
I had a standard contract, replete with a broad array of non-compete clauses. I then took on a chunk of the company as a Director and shareholder. I was offered 20% of the firm but retain my salary and commissions or 40% of the company but my compensation broadly paid in dividends and as tax efficiently as possible, without the salary or commission.
I didn't trust the two guys whom I was going into business with, so I took the 20% + salary + commissions. When I was given the shareholders agreement (SHA) to review, the SHA included all of my non-compete clauses as well. I didn't think too much of it at the time.
My resignation was an open and drawn out process, however having spoken to a couple of friends who are employment lawyers, they both indicated that the terms set out in the SHA would take precedence over the contract - i.e. my non-compete clauses didn't start the day I resigned, but started the day my SHA was cancelled. The two directors took absolutely ages to get the SHA cancelled - kept on delaying and delaying.
The result was that my 12 month non-compete clauses didn't start at the end of November when I resigned from my contract, but in fact began in June when the SHA was nullified. Fortunately I have no intention of breaching the non-compete clauses, but something to be wary of when reviewing the SHA.
