As the deadline looks on the winter NBA trade window, we look at the three losers from the most eventful windows of recent times. Teams have made multiple complex deals due to it being an on-season trade. And this is why desperate times call desperate measures but some teams have likely fumbled not only their current season but also the future ones through the trade they have gone on to conduct.Toronto Raptors are sitting at the 13th position in the Eastern Conference with a tanking record of 9-40 in 49 games so far this season. The front office was indeed looking for desperate measures and they made one on Thursday. In a multi team deal, Raptors got hold of Ingram while giving away 4 first round picks.Yes, 4 first-round picks for a player who has been constantly injured. On top of that, Brandon Ingram is in his final months of contract. What if he doesn't extend for the Raptors in the off-season? With such a desperate move, the Canadian franchise has not only gambled their current season but also their future ones.The Suns are another franchise that is tanking rapidly and are likely to not see the face of the playoffs. Clearly for them, the Kevin Durant, Devin Booker and Bradley Beal experiment hasn't worked out. All three players are on heft contract limiting the front office of any business. The Suns were close to letting Kevin Durant leave this week given his expiring contract at the end of the season.But Suns fumbled that deal and to make matters worse also the Jimmy Butler deal. How come you don't manage to bring a player both desperate for you and that gels perfectly well given the offensive woes. This one has to shake up the front office of the Suns.The story of Dallas Mavericks trading their young superstar player Luka Doncic made shockwaves through the NBA. In return, what they got was merely Anthony Davis and a draft pick. Even if, Dallas Mavericks had to move away from Doncic, the front office had all the time in the world to get what they wanted, to attract more assets. The General Manager and the whole management will have to reflect on what they just did.