I think there is more to this line that the obvious connection to Dave Free, Rich Baby Daddy, and both Kendrick and Drake’s respective versions of For Free. Drake is incredibly intentional with his bars and how he phrases certain things. Tons of sneak disses in FATD, Meltdown, etc. all make perfect sense with the hindsight we have now.

The lyrics begin to reveal themselves over time periods.

I wouldn’t be surprised if Drake smashed Whitney and is still sitting on the info. Especially after hearing Hi Whitney. I still think Hi Whitney is not AI and was Drake giving Kendrick a warning about what direction the beef would go, basically giving him a chance to bow out before shit got too personal.