2 aircraft cleared onto the same runway at the same time

This was a new one for me.

I was IFR this afternoon out of HPN for short practice flight. I was in
sequence number two at the runway waiting for departure. As the tower
controller cleared the Cessna in front of me to position and hold, he
asked him his direction of flight. The Cessna pilot responded
"Northbound". The controller then instructed the Cessna to position 50
feet north on Rwy 34, and then he cleared me to position and hold
behind the Cessna. The Cessna was VFR. I questioned the clearance,
reminding him that there was an airplane on the runway in front of me.
He told me to position and hold behind the traffic. As I taxiied into
position, he cleared the Cessna for takeoff and as soon as the Cessna
broke ground he cleared me for takeoff. I was using a DP which includes
a turn to the left. The Cessna was instructed to turn out to the right.

I've been flying out of HPN since 1992 and I have never seen or heard
of anything like this being done there before, ever.

Did I miss something??