If we look at Ben's attempts to secure a closer, he made 3 separate trades for high profile closer types-Bailey, Melancon and Hanrahan, all of which failed. He traded away quite a few players in the process-Reddick and Lowrie the only ones who may have been missed, I think.
Ben also signed Koji Uehara, which was a brilliant success and one of the best moves of his tenure.
Dombrowski went for the conservative and expensive play with Kimbrel. Dombrowski had come in for a lot of criticism in his tenure with the Tigers about his bullpens and closers. Tigers fans may forever believe they would have beaten us in 2013 if they had a real deal closer who wouldn't have blown Game 2.