Chelsea losing Willian and Pedro at the worst time to buy a new winger

LONDON, ENGLAND - OCTOBER 19: Willian of Chelsea and Ciaran Clark of Newcastle United during the Premier League match between Chelsea FC and Newcastle United at Stamford Bridge on October 19, 2019 in London, United Kingdom. (Photo by Justin Setterfield/Getty Images)
LONDON, ENGLAND - OCTOBER 19: Willian of Chelsea and Ciaran Clark of Newcastle United during the Premier League match between Chelsea FC and Newcastle United at Stamford Bridge on October 19, 2019 in London, United Kingdom. (Photo by Justin Setterfield/Getty Images)

Willian and Pedro will likely leave Chelsea this summer, which means the Blues will have a critical need in the most uncertain transfer market in history.

For obvious reasons, the near to medium-term future of football is all but guaranteed to be an absolute mess. Decision makers at every level are unable to offer much more than a collective shrug of the shoulders as to when football will return, how it will be organized, and what the off-field implications will be given the financial repercussions of the worldwide shutdown.

Of the many facets of football destined to resemble a Tilt-a-Whirl ride gone awry, the summer transfer market has the greatest chance to go into a complete tailspin.

At the moment, the very thought of spending money on transfers feels like an irredeemable sin. Any transaction that isn’t either paying non-playing staff or charitably funding the healthcare system would be considered outright villainous in the court of public opinion.

That sentiment isn’t likely to disappear in the next few months, even as sports eventually return to our lives.

And yet, despite the inevitable moral judgment, Chelsea have no choice but to dive headfirst into the murky abyss this summer.

The club’s current unenviable situation is partly a result of what now looks like an exceptionally ill-timed transfer ban. That, mixed with poor foresight in negotiations with current players, leaves Chelsea needing to bring in quality signings while presumably earning little to no money from outgoing players.

Pedro and Willian are the figureheads of the latter factor. Chelsea’s inability (or unwillingness) to extend the two wingers’ contracts means both are likely to leave on free transfers after the season ends. In Willian’s case, Chelsea were willing to break their typical policy of only offering one-year extensions to players over 30 by offering the Brazilian a two-year deal. Willian is demanding three years, and that’s apparently a bridge too far for Marina Granovskaia. Unfortunately, that means he’ll walk out door for free this summer.

Pedro’s situation is similar, albeit less damaging. Having made only 18 appearances this season, it’s clear that Frank Lampard doesn’t see a future for him at the club. In speaking with the club’s website, Pedro himself was uncertain at best regarding his contract situation.

The club has said it is postponing all negotiations for the time being, while Pedro is free to negotiate with any club for a summer move. The odds of him suddenly agreeing an extension — presumably for just one year — are unlikely.

So in a squad that would have benefited from reinforcements all season in other positions (i.e., left back, striker), another winger is suddenly the top priority.

If the new season kicked off tomorrow, Chelsea would have two first-team wingers in Christian Pulisic and Callum Hudson-Odoi, or three if you include the incoming Hakim Ziyech. All three are unknown quantities due to injuries, youth, or, in Ziyech’s case, having played his entire career in the Eredivisie. With Willian and Pedro headed for greener pastures, Chelsea absolutely need to bring in another winger, for the sake of both depth and some degree of consistent production.

The optimistic fan will immediately recommend Jadon Sancho. Unfortunately, though, Chelsea were reportedly drifting out of the race as Manchester United looked increasingly likely to pay Dortmund’s absurdly high asking price.

Given the inbound hurricane of economic uncertainty, the idea of Chelsea even considering a nine-digit transfer fee is laughable, at best.

Loathe as I am to say it, Manchester United’s seeming financial impenetrability makes them the only club (along with maybe Real Madrid) capable of writing that check with a steady hand. The best hope is that Dortmund hold onto him and Chelsea try again next summer, when Sancho will only have one year left on his contract. Unlikely, but one can dream, right?

Who, then, are the more practical names? Well… there really aren’t any, at least none who have been linked to the club.

Most of the recent Chelsea rumors are focused on fullbacks and goalkeepers, with the odd Lautaro Martinez or Luka Jovic thrown in to bait some clicks.

The closest thing to a realistic option is — and I hate to even type this for fear of speaking it into existence — Philippe Coutinho. A massive fee to loan a player who was deemed not good enough to consistently feature for underperforming Barcelona and Bayern Munich sides? Hard pass.

There are certainly players out there who would fit the bill. Maybe it’s a Jack Grealish or Leon Bailey, or perhaps a Lorenzo Insigne or Wilfried Zaha. But with so many clubs in such an extreme state of financial flux, the availability of anyone of value is entirely unknown. You have to imagine that many clubs will try to hold onto whatever assets they have. And yet, Chelsea will need to at least knock on all of those doors.

Grim as that may sound, there is another interpretation of how things could shake out. There’s no question that a number of top clubs aren’t exactly financially secure, Tottenham being one reported example. Those clubs running on tight budgets will most likely need some short-term injections of cash to pay all their wages, debts, and other expenses. The more well-funded clubs, Chelsea being one of them, should smell blood in the water. They certainly wouldn’t be the only buyers, though, and a bidding war for anything other than a player who is an absolute sure thing could be disastrous.

There’s opportunity, but it will take some expert maneuvering.

All of this is to say that Chelsea will be walking into a market where reasonable deals are few and far between. Chelsea may go in looking for a pack of four-ply toilet paper, but leave with a single box of store-brand paper napkins. Or, they may overpay for a bidet that never works properly.

In times of uncertainty, it’s not easy to be an effective shopper. There most likely is a mega-pack of Charmin Ultra Soft out there somewhere, but Chelsea will need to be quick and quiet in order to get their hands on it. What an exhausting metaphor.

The Ben Chilwell’s and Gianluigi Donnarumma’s of the world would undoubtedly be useful additions to the squad, but they aren’t absolute necessities. When it comes to wingers, though, Chelsea have painted themselves into a corner, and they’ve left themselves with no option but to go shopping for one this summer.

At this point, no one really has a handle on how the next few months will shake out in the football world, or the world in general. Chelsea’s main objective should be clear though: replace the Willian / Pedro spot in the squad.

It will be tough sledding to find the right fit, but the right player could give Chelsea a major boost in what is sure to be a wildly unpredictable 2020/21 season.