Sorry, I didn't explain it very well. Either way, if his contract expires, he can leave. However, if we have offered him a greater or equal contract to his current one, we would be entitled to compensation from any new club he was to join. This was the case when Grant Hall left us for Spurs IIRC.
Not if we've offered him a contract of greater or equal terms to his current one, no. I'm sure he would end up leaving in these circumstances, but we would be entitled to compensation from whichever club he joined.