An example of how Ujiri and Webster differed: it was Ujiri who was resistant to signing Pascal Siakam to an extension in the season prior to him being traded to the Indiana Pacers in January of 2024. Ujiri didn’t want the risk of a long-term deal on his books for a player who he was no longer sure was a fit with Scottie Barnes’ timeline. An injury to Siakam after he signed, or even just a downturn in performance, would have left the Raptors in a difficult situation. But not signing him also meant that they had less control over where Siakam could be traded as he headed into the final year of his contract, likely less leverage for extracting a top price. Webster was in favour of extending Siakam, which would have given the Raptors more control in the trade market if they wanted to go that route, as they would be trading a player under team control for multiple years.