Cyrus, and any federal employee or official, is barred from accepting only certain gifts, not all gifts. He can accept a gift of any value from a friend, for instance, but not any gift that could be seen as corrupt or attempting to sway him politically. Fenton Glackland's gift is a borderline case, because he is a top political donor, and wanted a favor from Cyrus: helping him with politics. Fenton may only have had innocent advice and mentorship in mind, or unethical work on the part of the White House to endorse him in a race. On the other hand, Fenton has feelings for Cyrus and could make the case the gift was entirely out of personal affection.
In any case, no official must make this call on their own, and Cyrus could put the case to ethics officials for guidance (and, given the painting's value, would be required to disclose the gift to an ethics body). Unfortunately, the loophole he found--paying Fenton a token amount for the painting, as gifts under $20 won't receive scrutiny--doesn't hold water. Federal guidelines are clear enough about valuing an object's worth that such an unethical accounting measure would not only still be proscribed (if the gift itself is unethical) but the deception would also set Cyrus up for being accused of graft.
In any case, no official must make this call on their own, and Cyrus could put the case to ethics officials for guidance (and, given the painting's value, would be required to disclose the gift to an ethics body). Unfortunately, the loophole he found--paying Fenton a token amount for the painting, as gifts under $20 won't receive scrutiny--doesn't hold water. Federal guidelines are clear enough about valuing an object's worth that such an unethical accounting measure would not only still be proscribed (if the gift itself is unethical) but the deception would also set Cyrus up for being accused of graft.