Loser - Philippe Coutinho
Last January was truly monumental for Liverpool, and could one day be looked back as the transfer window that began Liverpool's ascendance back to the upper echelons of European football. Liverpool sold star man Coutinho to FC Barcelona for an initial £105 million, rising up to a £142 million in bonuses and appearance clauses. That money helped Liverpool buy Naby Keita and Virgil Van Dijk, both of whom will certainly be pillars of the Liverpool side we will see for years to come.
The flashy little Brazilian wanted to leave in search for trophies and success, both of which he certainly will get at Barcelona, but his status has certainly taken a nosedive, as he is no longer the same kind of attacking threat as he was during his time at Liveprool, mostly due to the role he now fulfills in the system at Barcelona.
Instead of having the game go through him, he's just another guy in the team now. Not that that's a bad thing, especially when you're at Barca. His team's defeat and elimination at Anfield feels a bit like make-believe, but it's also quite poetic.