The Toronto Maple Leafs are shaking things up with some significant signings, adding Chris Tanev to their roster with a six-year deal while Jani Hakanpaa's NHL future remains uncertain. Hakanpaa, previously teammates with Tanev on the Dallas Stars, missed the playoffs due to his severe knee injury. Currently, there's no timeline for his return to the ice. <div align='center'><blockquote class='twitter-tweet' data-lang='en'><a href='https://twitter.com/sportsnet/status/1807866547169632557'> </a></blockquote></div> Steve Simmons of the Toronto Sun highlights the grim reality facing Hakanpaa. <q> A year ago, maybe two years ago, Hakanpaa would have factored rather nicely on the Leafs defence. He's a giant of a man at 6-foot-7, popular in the room, that great hockey vernacular, and a penalty-killer beyond compare. But one with a knee so bad that some think — although the Leafs disagree — that he may never play again. The Leafs signed him to play but many doubt he will. It's said to be bone-on-bone with not much knee left. It's said to be trouble. Two years ago, Hakanpaa was playing 18 minutes for the Stars. He might have played his last NHL game in March. If he plays again, plays at all for the Leafs, it will shock those who were around in recent seasons. </q> With doubts about his knee condition, the decision to ink a deal is interesting. Despite the Leafs' optimism, outsiders aren't sure Hakanpaa can return to the NHL. It's possible the investment by GM Brad Treliving can be for naught. <div align='center'><blockquote class='twitter-tweet' data-lang='en'><a href='https://twitter.com/thetorontosun/status/1807922149350400442'> </a></blockquote></div> As seen on Daily Hockey Dose: <a href='https://www.dailyhockeydose.com/nhl-team/toronto-maple-leafs/bad-news-confirmed-for-jani-hakanpaa-and-the-toronto-maple-leafs' class='lien_marqueur' target='_blank' rel='noopener'>Bad news confirmed for Jani Hakanpaa and the Toronto Maple Leafs</a>