#2 Loser: Gennaro Gattuso and Milan

Ultimately, Milan's faith in Higuain was well and truly shattered. The move was bold, though it was only going to be a masterstroke acquisition or a flop that massively backfired. It has.
Krzysztof Piatek joined for a reported €35m (£30.5m) earlier this month from Genoa and already netted a brace on his full Milan debut during their Coppa Italia win vs. Napoli last night. The Polish forward, 23, has plenty of upsides and is enjoying a breakthrough campaign in Italy's top-flight, but the Higuain deal was a serious investment, even temporarily, for a striker with a pedigree in the division.
Not as though they were taking a gamble on a youngster with no experience nor someone who had yet to acclimatize to the league, Higuain has been there for five years!
Despite flashes of progression, the team isn't yet good enough to get into the Champions League and players like Higuain prove an unnecessary hindrance. Gattuso hasn't had to deal with this type of personality before during his managerial career to date, it isn't unclear whether he even privately approved of the deal.
It's poor and frustrating for a team seemingly on the up, who are slowly but surely aiming to return to their glory days. Luckily for them, Piatek is flourishing and they have a young core of players hungry to prove themselves.