Yes he did. on 2 different occasions actually.
he tried to get him at the 2016 draft but as I heard, Pittsburgh wasn't doing it for less than a first round pick. Flames took Tkachukk that year.
He tried again the deadline but Pittsbrugh worked out a deal with Vegas to ensure that MAF was going to be their selection in the expansion draft. They didn't want to lose their young dman at the time, Doumalin in particular.