In 2022, Chicago traded Alex DeBrincat to Ottawa in the afternoon before the first round of the draft for three picks, including 7OV.
And I don't think any of these happened with the team on the clock.
2022: Alex DeBrincat for 7OV, 39OV, & ’24 3rd
Alexander Romanov & 98OV for 13OV
Kirby Dach for 13OV & 66OV
Kevin Fiala & rights to Brock Faber for 19OV
2021: Oliver Ekman-Larsson & Conor Garland for Loui Eriksson, Jay Beagle, Antoine Roussel, 9OV, 47OV, & 203OV
Seth Jones, 31OV, & ’22 6th for Adam Boqvist, 11OV, 43OV, & ’22 1st (top 2 protected)
Rasmus Ristolainen for Robert Hagg, 13OV, & 39OV
2020: Kasperi Kapanen, Pontus Aberg, & Jesper Lindgren for Evan Rodrigues, Filip Hallander, David Warsofsky, & 15OV
What trade are you thinking of?