Two 310 Telestos in 20 minutes. (Did Nightfall, Three of Coins dropped an special Engram, Nightfall gave me a 310 Telesto, went to the tower and decoded the Engram, got another 310 Telesto) I can't think of anything worse, because I have generally good luck in this game. I got 9 Hawkmoons in year one (first was from a legendary Engram...) and my first VoG hard gave me Fatebringer and Vex Mythoclast in the same run, just for some examples.