On March 10, 2019, the Raiders agreed to trade Osemele and a 2019 sixth round draft pick (originally acquired from the Chicago Bears) to the New York Jets in exchange for a fifth round pick. The deal was completed on March 14, 2019. On October 15, 2019, it was revealed that Osemele suffered a shoulder injury and was contemplating surgery. Osemele’s doctors told him that he needed surgery for his injury, but the Jets organization was not approving his surgery, so he was fined for every practice that he missed due to his injury. On October 26, 2019, Osemele was released from the team after undergoing shoulder surgery.