45. William Nylander
Nylander made the Maple Leafs sweat in 2018 when he took his contract negotiations down to the wire. The deadline was 5 p.m. and Nylander signed the deal at 4:55 p.m.. This was because he wanted the franchise to prove its commitment to him moving forward (via Sporting News).

He threatened to leave his teammates high and dry if the franchise didn’t bow down. If Nylander failed to sign, he would have sat out the remaining games of the season. This wouldn’t have helped anybody except himself. Nylander became unpopular when his form declined after the deal.