The politics of Oscar wins are complicated and often people end up winning not for the particular piece of work they were nominated for, but either for their whole body of work or for something they were overlooked for previously. Not saying it will happen because there is likely to be stiff competition but Timmy could win as a way to welcome him formally to the Hollywood A list, or as a kind of late recognition for CMBYN (for which he would’ve been a more deserving winner than Oldman that year, but Oldman was also winning for his entire body of work, etc).