Law already has deep connection with Drake and they are probabaly collaborating together lowkey, a lot of hints point at that:
They met in Sabaody and had a particular interaction
Law is the only one who, during the 2 years TS, decided to become a Shikibukai.. going near the WG/Navy.
They share the same flashback, losing their 'father figure' (be it good or bad) the same night, on the same island, in the same Ope-Ope deal
Drake is an undercover operative (same profession as Cora) working for SWORD
and another SWORD member is Coby, considered the hero of the mysterious Rocky Port incident
The same incident of which Law is considered the mastermind
After Doflamingo defeat, Drake reacted in an enigmatic way to the news when reading about Law
In Wano, Hawkins noted how Drake was behaving strangely after Law's capture
and Drake himself later freed him, in this occasion they met each other again (last time on panel was Sabaody) and even here the dialogue is pretty enigmatic
This way Drake blowed his cover,
for Law
Now, I think is clear that these 2 have a connection and that SWORD is involved.
Don't know when/where/why, but these 2 will have a common objective in the future, after Onigashima.