Also, DT's buying on market was nothing whatsoever to do with...

Also, DT's buying on market was nothing whatsoever to do with the process of cashless conversion.

He committed to spend the money he "saved" by doing cashless conversion to buy up additional shares on-market. This is a win-win for the shareholder... cashless conversion means fewer new shares issued to DT (less dilution), plus more of the on-market supply is soaked up and locked into DT's diamond hands (these shares are effectively removed from the market).

The "loser" in this case is Race the company, as it did not receive any money from DT in exchange for the shares issued.

There is still dilution in the case of cashless conversion, as new shares are issued by the company. However, the number of shares issued under cashless conversion is always less than the number of options being converted.