8. Jonathan Drouin to the Montreal Canadians (2017)
From the get-go, it was clear that Tampa Bay would have their hands full with Jonathan Drouin. A third overall pick in 2013, Drouin looked to be an excited winger for the Bolts. Despite some early promise, problems arose in January 2016 when he was suspended indefinitely by the team. Drouin had previously requested a trade and his agent had tried to force the move through. As a result, Tampa had attempted to send him to AHL side Syracuse Crunch while a trade was worked out. Drouin refused to report resulting in suspension.
It was made apparent that he had no desire to play for the side that drafted and wanted a move immediately. GM Steve Yzerman was put in an untenable situation and advised they were looking for a potential suitor. Finally, two months later Drouin reported to Syracuse and the stand-off ended. While he would continue to play well for the Lightning in the remainder of the season, the hierarchy was irked. Keen to be rid of their disgruntled star, the Bolts traded Drouin to Montreal for Mikhael Sergachev, a conditional second-round pick and a sixth-round pick.
Tampa Bay went to claim their second Stanley Cup three years later. While Drouin has performed consistently for the Habs, you have to wonder what could have happened had this stand-off not occurred?