Reese and Finch are pretty certain that the person associated with the next number dispensed by the machine is going to be the perpetrator of the upcoming crime. He is mob enforcer Riley Cavanaugh, who works for a mid level gangster named George Massey. That is why they, but especially Finch, have mixed feelings when they learn that Riley is the intended target. Reese, however, looks at the bigger picture when they learn that Riley is protecting an innocent party, she being Annie Delaney, the widow of one of Massey's former thugs. Massey had always been attracted to Annie, but instead Annie and Riley fell in love after the death of her husband, about which Massey does not know, or so Annie and Riley believe. The difficulties of this case include different people targeting Riley and Annie which means that Reese and Finch have to keep abreast of these different groups; Riley having no qualms about killing even Reese, the mysterious suited man following and seemingly helping him; and Carter having to throw her colleagues off the trail during a murder investigation as they they themselves track Riley. Finch calls in some help from an unusual source, who has an unusual request of his own in return.