New York Yankees General Manager Brian Cashman made a lot of moves to help bring the team to 99 wins, but not all were successful. Being a MLB General Manager is one of the hardest jobs in sports, as you get blamed for losses and are rarely credited for the wins. The team that Cashman has built is able to challenge the best the American League has to offer, but glaring mistakes still slow them down.The biggest move made by Brian Cashman in the offseason was the acquisition of Josh Donaldson and Isiah Kiner-Falefa. In exchange, the New York Yankees sent Gio Urshela and Gary Sanchez to the Minnesota Twins. With the benefit of hindsight, many Yankees fans point to this move as what is holding the team back.New York Yankees fans do not need any added motivation to criticize their team when they believe a mistake has been made.Max Mannis@MaxMannisAll things considered, the IKF/Donaldson deal might legitimately be Brian Cashman's worst trade of my lifetime (December 2001)154244All things considered, the IKF/Donaldson deal might legitimately be Brian Cashman's worst trade of my lifetime (December 2001)Acquiring a player of the caliber of Josh Donaldson makes sense on paper, but has certainly not played out the way Brian Cashman hoped. Donaldson is seven years removed from his MVP season and six years removed from his last All-Star selection. Expecting him to reach those heights once again in the 12th year of his career was a stretch.Larry McCulloch@LarryMcCulloch5You got that right!!! twitter.com/MaxMannis/stat…Max Mannis@MaxMannisAll things considered, the IKF/Donaldson deal might legitimately be Brian Cashman's worst trade of my lifetime (December 2001)154344All things considered, the IKF/Donaldson deal might legitimately be Brian Cashman's worst trade of my lifetime (December 2001)You got that right!!! twitter.com/MaxMannis/stat…Rapheal Suarez Gonzalez (temp Astros fan)@RedsoxDevers@MaxMannis Seems I was right once again little Maxy twitter.com/redsoxdevers/s…Rapheal Suarez Gonzalez (temp Astros fan)@RedsoxDeversYankee fans will hate josh Donaldson by June.1Yankee fans will hate josh Donaldson by June.@MaxMannis Seems I was right once again little Maxy twitter.com/redsoxdevers/s…Billy 🕸er🎃👻⚾️@Bwebs622I hated the IKF part of the trade for obvious reasons, but I thought they would get a lot more out Donaldson twitter.com/maxmannis/stat…Max Mannis@MaxMannisAll things considered, the IKF/Donaldson deal might legitimately be Brian Cashman's worst trade of my lifetime (December 2001)154344All things considered, the IKF/Donaldson deal might legitimately be Brian Cashman's worst trade of my lifetime (December 2001)I hated the IKF part of the trade for obvious reasons, but I thought they would get a lot more out Donaldson twitter.com/maxmannis/stat…At best, this trade is seen as a net equal, having no strong impact on the season. The Yankees still managed to win 99 games, good for second best in the American League. However, playing in New York means playing with heightened expectations. Brian Cashman and everyone in the Yankees organization are well aware of this fact.Kevin Ray@whatthefach@MaxMannis Eh, bad assets for bad assets. Kind of a wash in the end. At least there was a little spark sometimes.2@MaxMannis Eh, bad assets for bad assets. Kind of a wash in the end. At least there was a little spark sometimes.Charlie HP@accord5speed@MaxMannis looks bad now but earlier on the season they were unstoppable when Donaldson was actually hitting which allowed them to get a 15 game lead@MaxMannis looks bad now but earlier on the season they were unstoppable when Donaldson was actually hitting which allowed them to get a 15 game leadEl Coyote@kbo_coyote@MaxMannis Could be noted that the Yankees have out-lasted 26 other teams to get this far.1@MaxMannis Could be noted that the Yankees have out-lasted 26 other teams to get this far.While the Donaldson and Kiner-Falefa trade was the primary move Cashman made, they also acquired pitcher Frankie Montas. Unfortunately for them, Montas has also under-delivered and is another mark against Cashman. Much like players, general managers can only make so many mistakes before the team looks to move on.Bobby tam@Bobbytam333@MaxMannis Montas was pretty bad also2@MaxMannis Montas was pretty bad alsoredbow@chawheeelgrandeHopefully it gets him fired. But it won’t. twitter.com/maxmannis/stat…Max Mannis@MaxMannisAll things considered, the IKF/Donaldson deal might legitimately be Brian Cashman's worst trade of my lifetime (December 2001)154444All things considered, the IKF/Donaldson deal might legitimately be Brian Cashman's worst trade of my lifetime (December 2001)Hopefully it gets him fired. But it won’t. twitter.com/maxmannis/stat…Kevin Schappert@SchappertKevin@MaxMannis Maybe so.It was horrible. And it will get worse when JD sits next year when Volpe arrives.@MaxMannis Maybe so.It was horrible. And it will get worse when JD sits next year when Volpe arrives.The Yankees have built a strong team, but there will always be fans who expect nothing but the best.Brian Cashman has been the decision maker for the New York Yankees since 1998League Championship Series - Houston Astros v New York Yankees - Game FourCashman has built the Yankees over the past 20 years, and some fans believe that his time is coming to an end. With the amount of money the Yankees put into their roster, a World Series is expected every year. They have not won it since 2009. Brian Cashman has done great things in his tenure with the Yankees, and only time will tell what more he can accomplish. But as things stand, he is under increasing pressure to deliver.