16 weirdest moves of the summer transfer window

Updated: September 3, 2019

Last summer, some of the most outlandish and unexpected transfers included Paulinho to Guangzhou Evergrande, Gervinho to Parma, Eric Choupo-Moting to Paris Saint-Germain, and Marco Borriello to Ibiza.

A year later, and 2019’s showpiece shopping season was as peculiar, with clubs making additions that raised eyebrows and elicited guffaws. Here’s a look at the 16 weirdest transfers of the summer window in no particular order:

Bojan Krkic (Montreal Impact)

From La Masia prodigy to breaking Lionel Messi’s record for youngest Barcelona debutant to a cold Tuesday night at Stoke City, 28-year-old attacker Bojan Krkic‘s footballing slump has now landed him in MLS. The two-time Champions League winner penned a year-and-a-half deal with the Montreal Impact on Aug. 7 and opened his account in style. Time to read this gem again.

Shinji Kagawa (Real Zaragoza)

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Few players are as synonymous with Borussia Dortmund‘s modern successes as Shinji Kagawa. The Japan international made 148 league showings over two spells, bagging 41 goals on the way to two league titles, but after being exiled on loan to Besiktas, an exit seemed inevitable. Few would have guessed that it’d be to the second tier of Spanish football with Real Zaragoza.

Jasper Cillessen/Neto (Valencia/Barcelona)

In July, Barcelona sold ‘keeper Jasper Cillessen to Valencia for €35 million. The next day, Los Che sent shot-stopper Neto to Barcelona for €26 million with €9 million in add-ons. Valencia made a vital sale before the July 1 Financial Fair Play year’s end, while the Catalans curried favor with a potential destination for Denis Suarez and Rafinha. Shady.

Kieran Trippier (Atletico Madrid)

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Following a stellar 2017-18 campaign, Kieran Trippier was one of several Three Lions mired in a post-World Cup hangover while with Spurs last season. Somehow, the 28-year-old right-back overcame that drop in form to secure a €22-million move to Atletico Madrid. Trippier is now just the 20th Englishman to ply his trade in Spain’s top flight. Try the huevos rotos, Trippy.

Radja Nainggolan (Cagliari)

Who could have foreseen Radja Nainggolan‘s swap move to Inter from Roma for Nicolo Zaniolo and Davide Santon going so poorly? Zaniolo is a budding star, while the robust Belgian was, for the most part, a waste at San Siro, prompting a return to Cagliari on loan five years after the mohawked merchant of missiles last plied his trade in Sardinia.

Daniele De Rossi (Boca Juniors)

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Like Francesco Totti before him, local boy Daniele De Rossi had become a Roma emblem on the way to registering 616 appearances for the club. The 36-year-old midfield bulwark’s summer switch to Boca Juniors was a shock, even with former Giallorossi mate Nicolas Burdisso acting as sporting director with the Argentines.

Jason Puncheon (Pafos)

If you thought Lewes’ famed Dripping Pan ground was the most random place veteran Jason Puncheon has called home, well, we have news for you. The Croydon-born 33-year-old has signed with Cypriot minnows Pafos, who in their six-year history count ex-Scotland defender Steven Pressley as a former manager. Ah well, at least we’ll always have this objectively hilarious bathroom break.

David Luiz (Arsenal)

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Considering Chelsea are hampered by a transfer ban, the decision to sell wantaway center-back David Luiz to rivals Arsenal for a scant £8 million came as a surprise as the Gunners sought a stopgap at the back. Floppy-maned Luiz reminded Arsenal supporters of his error-prone ways when he was at fault for the penalty versus Liverpool and oddly out of position for the Reds’ third goal.

Lee Cattermole (VVV-Venlo)

Anyone privy to Netflix’s stellar “Sunderland Till I Die” docu-series will have fond memories of Black Cats disciplinary misfit Lee Cattermole, and now those who fancy the top-tier of Dutch football can relive it all. The 31-year-old moved to Eredivisie lot VVV-Venlo in the summer, and a yellow card on his first foul amounts to the most felicitous thing in football.

Wayne Rooney (Derby County)

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England legend Wayne Rooney is set to cut his MLS tenure short with a casino-funded move to Derby County sponsored by bookies 32Red. It figures that the follically challenged forward would fancy any form of a plug, which in this instance is for an industry whose negative influence on English football knows no limits; Rooney will sport the No. 32 kit as a death knell for subtlety.

Ravel Morrison (Sheffield United)

Few footballers have experienced a career arc as unique as former Manchester United academy prodigy Ravel Morrison. Mercurial terms across England saw the midfielder enjoy a stretch with Mexico’s Atlas and a cup of tea with Swedish upstarts Ostersunds, and now, the 26-year-old has made Bramall Lane his latest stop on a one-year deal with Sheffield United.

Malcom (Zenit St. Petersburg)

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Malcom was set to join Roma last summer, but as fans waited for the winger at the airport, the 22-year-old signed with Barcelona. He barely got a match at the Camp Nou before a €40-million move to Zenit this summer. The Russians poked fun at Roma with their announcement, then Zenit fans racially abused Malcom on his debut. Hard not to feel for the lad.

Kemar Roofe (Anderlecht)

Striker Kemar Roofe played a massive part in Leeds‘ perpetual flirtations with promotion, but with a year left on his deal at Elland Road, the 26-year-old made an unlikely move to Anderlecht. It hasn’t quite gone to plan under Manchester City legend Vincent Kompany, whose player-coach role has been curtailed with two defeats and two goalless draws through five fixtures.

Nabil Fekir (Real Betis)


A year on from a reported €60-million transfer to Liverpool that broke down last June over a dodgy medical, Nabil Fekir moved to midtable Real Betis from Lyon for €19.75 million plus a potential €10 million in add-ons. What? Another shrewd move for a Betis side that secured Giovani Lo Celso‘s services from PSG for €22 million before flipping him to Spurs for a potential €60 million.

Vincent Janssen (Monterrey)

Managing a scant six goals in 42 appearances following a move from AZ Alkmaar in 2016, Vincent Janssen might as well have opened a fish-and-chips shop in Tottenham‘s vacant trophy case after Mauricio Pochettino admitted the Dutchman had no future in north London. Naturally, the next step was a switch to Liga MX’s Monterrey. Will he be the next Andre-Pierre Gignac? No.

Martin Skrtel (Atalanta)

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Atalanta‘s first foray in the Champions League begged for reinforcements, and that’s exactly what Gian Piero Gasperini’s lot got in landing former Liverpool center-back Martin Skrtel. Three weeks later, and with one match played, “mutual consent” nixed the deal following an alleged row with Gasperini. Hours after that, Skrtel signed with Istanbul Basaksehir. Veni, vidi, vamoose.

Honorable mention: Remy Cabella (Krasnodar), Andre Schurrle (Spartak Moscow), Ivan Perisic (Bayern Munich)

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