I'm not sure why people aren't getting this.
If you trade or release him in the off-season, or he decides to retire before June 1st, this is how it works:
*The remaining prorated bonuses immediately accelerates. That's $19,600,00 (2017 - $10.7M, 2018 - $5.7M, 2019 - $3.2M).
*His 2017 salary cap hit is scheduled to be $24,700,00, the combined total of his 2017 prorated bonus of $10.7M and his 2017 base salary of $14,000,000. So $24.7M minus $19.6M equals $5.1M in additional cap room (slightly less since the 52nd highest salaried player now counts against the cap).
*Romo' s contract is completely off the books when the 2018 season officially begins.
If he is released or decides to retire AND is designated a June 1st cut, this is how it works:
*His 2017 prorated bonus of $10.7M immediately hits the cap, freeing up $14M (his base salary) in cap room, BUT not until June 1st, 2017. Most players have signed new contracts well before June 1st.
* The 2 remaining years of prorated bonuses (2018 - $5.7M, 2019 - $3.2M) hit the 2018 salary cap, meaning $8.9M of dead money from Romo will be on the cap, even though Romo will have been gone for over a year by that time.