This is baseball, not Monopoly. "Winning" the trade market doesn't guarantee making the play-offs.
Not making a trade is the least of the Twins problems. Tying up a good chunk of the payroll on two unproductive "stars", signing declining vets instead of promoting in-house prospects, rigid, unimaginative coaching by stats, puzzling lineups, swinging for the fence on most every pitch, leading the league in strikeouts, poor bullpen management... the list is practically endless.
The only "trade" that will fix the Twins is a swap for a whole new front office and coaching staff.