Liverpool were hours away from landing both Alexander Isak and Marc Guehi on the same deadline day. One of those deals actually happened. The story of the one that didn't is a genuinely painful "what if."
Isak's British-record move from Newcastle is history now — confirmed, completed, and a major part of Liverpool's attacking picture this season. What's less remembered is that Liverpool were simultaneously closing in on a second major deal that same day: a £35m agreement with Crystal Palace for captain and England international Marc Guehi.
This wasn't speculative transfer gossip. Guehi started and captained Palace in a 3-0 win at Aston Villa, scoring a brilliant curling goal, then was given permission to travel for a medical in London the same day. Personal terms were agreed. The medical was passed. By every normal measure, this deal was done.
It collapsed anyway. Crystal Palace pulled out with hours left on the clock because they hadn't sourced a replacement centre-back in time, reportedly under pressure from manager Oliver Glasner not to sell without cover in place. Guehi, by multiple accounts, was upset — he'd already told Palace he wanted the move.
Guehi had already made clear he wouldn't be signing a new Palace contract. That set up a straightforward expectation: if the summer deal fell through, Liverpool would simply return for him as a free agent when his contract expired. Instead, Manchester City moved first — agreeing a deal with Palace in January 2026 after injuries to Josko Gvardiol and Ruben Dias made a mid-season centre-back a priority for them. Liverpool, by most reporting, never even made a formal bid that window. Palace accepted a fee from City reportedly lower than what Liverpool had already agreed to pay months earlier.
Two chances, two misses, and a player who wanted to join in the first place ending up at a direct rival.
Picture the version where Palace found their replacement in time. Isak and Guehi arrive on the same day — a statement of intent that would have been the headline of the entire transfer window. A settled, England-international centre-back partnership alongside Virgil van Dijk, with Jeremy Jacquet developing in the background rather than being rushed into the picture. One fewer defensive question mark heading into a season that was always going to be defined by change at the top.
Instead, Liverpool head into this campaign with real centre-back questions still unresolved, and a player who wanted to be at Anfield now lining up for a direct title rival instead. Few "what ifs" in recent Liverpool history sting quite as specifically as this one — not because it was unlikely, but because it was already agreed, medically cleared, and lost in the final hours anyway.