Clint Dempsey to Liverpool, Weston McKennie to Cincinnati, Antonee Robinson to Milan: Wildest failed USMNT transfer sagas

It's wild to think just how much this would have changed the course of Premier League history.

The year is 2012 and Clint Dempsey seems all but set to go to Liverpool. Struggling midfielder Jordan Henderson would go the other way to Fulham. By all accounts, the deal was essentially done. Liverpool even accidentally posted a video on their official website confirming Dempsey's imminent arrival.

"We never talk publicly about our transfer targets," Liverpool chairman Tom Werner told GOAL at the time. "However, any team would be lucky to have Clint Dempsey playing on their squad."

"Clint's a player that we have inquired about," added then-Liverpool boss Brenden Rodgers. "It's as simple as that. Ian Ayre, our managing director has spoken with the club [Fulham] to see what the position is. And that's where it's at. So there's been nothing more than that. He's obviously a very talented player but we don't like to speak on other club's players. But that's as far as those went really. There's nothing else more."

The deal, though, was never consummated. And after it fell through, Fulham manager Martin Jol then publicly accused Dempsey of refusing to play. Complaints were filed. Investigations began. It got relatively ugly.

''I was probably a bit naive, asking, 'Clint, do you want to start?''' Jol said after a win over Norwich. ''All he said was, 'You know what I want' ... after that it was very difficult to communicate. He was not committed to the team."

Dempsey ultimately did get a big move, but not to Liverpool, as he moved to Tottenham later that summer. Henderson, meanwhile, survived another day at Liverpool, going on to captain the club to every trophy imaginable. Imagine how different things could have been.

For years, it's seemed as if Antonee Robinson has been linked to every team under the sun. Chelsea, Liverpool, Manchester City - all came into speculation. But the closest was AC Milan. It was just a medical away.

In January 2020, Robinson had agreed to a deal to leave Wigan for Milan in a $13 million transfer. It was a shocking step up. Here was AC Milan, one of the most legendary clubs, signing a fullback from the Championship? Unfortunately for Robinson, it was never completed. The medical revealed that Robinson had a heart irregularity and further testing couldn't be completed before the deadline, spiking any hopes of a deal.

"Being linked with clubs, especially after the AC Milan thing, me personally, it's obviously nice to see things like that," Robinson said a year later, "but I don't really take too much out of it because I just want to get on with the job that I'm doing at the club I'm at.

"You never know what's gonna happen in football. I don't like to get my hopes up or anything so I just work hard where I'm at and the rest will take care of itself another time."

Milan's interest was ultimately validated, with Robinson going on to establish himself as one of the Premier League's best left-backs at Fulham.

Back in 2014-15, Dempsey, Jozy Altidore and Michael Bradley changed the game. Despite being in-their-prime USMNT stars, they returned home to MLS. At that time, those were stunning moves - and they helped lift the league.

This past summer, McKennie reportedly had a similar opportunity. Frozen out at Juventus, FC Cincinnati came knocking and, according to reports, they almost pulled it off.

According to GiveMeSport, Cincy pushed hard for McKennie, beginning their pursuit earlier this year. They visited McKennie in Italy to sell their vision. McKennie, in turn, visited the club back in the States and met up with club leadership. In the end, though, McKennie earned a Juventus stay, signing a new deal with the club.

Cincy didn't stop with McKennie, however. They also pursued Josh Sargent but, in the end, came up short there as well. Either signing would have certainly changed the dynamic of the USMNT while also changing the perception of FC Cincinnati going forward.

This one always seemed more myth than reality, as if fans were trying to speak it into existence. But the rumor circulated for years.

During Pulisic's rise at Borussia Dortmund, he certainly impressed then-manager Jurgen Klopp, who was never shy when it came to making his feelings known about the American.

"At the moment he has a contract with Dortmund," Klopp said of Pulisic back in 2018. "He’s still pretty young and he’s at the perfect place for his development, but if he ever wants to come to England he’s more than welcome."

We all know what happened next. Pulisic went to Chelsea but, even while he was wearing blue, there was still speculation that he could someday wear red. That ended up happening, but it turned out to be the black and red of AC Milan, where he landed in 2023 in a transfer that now feels like a masterstroke.

All the while, Klopp remained an admirer, going so far as to praise Pulisic in one of his final interviews as Liverpool boss.

"When I left Dortmund, Pulisic came through," Klopp told the Anfield Wrap, "so I had him as a 16-year-old in training and I thought 'Oh my God! Wow!' And then you see him later, at Chelsea, doing well now at AC Milan. I would love to stay with all the people in the building."

And while it never actually seemed that close to coming to fruition, it does make you wonder: what if?

After Leeds' relegation, Tyler Adams was going somewhere. The question was where.

For a while, it appeared to be Chelsea. By transfer window standards, the deal was moving along in all the right ways. The Blues had bid $25M (£20m) to sign him, personal terms looked good and a medical was scheduled. Unfortunately for Adams, that medical seemed to undermine the deal.

According to reports, Adams' hamstring injury led to Chelsea pulling out of the deal at the last minute, with the club instead turning their focus towards Moises Caicedo and Romeo Lavia - they would ultimately sign both for boatloads of money. Adams, instead, went to Bournemouth, but has been limited by injuries throughout the last year.

Would Chelsea have gone on their midfield spending spree if the Adams deal was locked up? Would Adams have just gotten lost in the shuffle at Chelsea anyway, as numerous other players already have during the Todd Boehly regime? Maybe it'll work out best for everyone that it didn't go through.

Out of all of the ones on this list, this just may be the wildest.

Duncan McGuire had signed with Blackburn. Everything was apparently done. A fee was agreed, a contract was signed and the deal was complete. All that was left to do was file the paperwork.

Yeah... about that.

When filing the paperwork to complete the transaction earlier this year, Blackburn hit "save" and not "submit" on the documentation. They didn't fix the error until after the window closed, causing them to miss the deadline for submission, despite both Blackburn and Orlando City announcing the completed deal. An appeal was denied and McGuire was forced to awkwardly return back to Orlando.

"That was a pretty bad mistake, a pretty bad mistake by them," McGuire told GOAL in May. "I'd be open to maybe having a conversation but it would have to be a lot to get me to go back there. On the plane ride back, I just felt like my tail was between my legs. I asked my agent how often this happens and he was like 'This doesn't happen'.

"I didn't burn bridges with my teammates or have it be like 'Oh you wanted to leave and now you're back'. When I got back, it was like I never left."

McGuire has since signed a new deal with Orlando, but Europe remains in his future. Let's just hope that the next time, the club ticks the correct box to send the deal through.