Winners and losers from Tottenham signing Andy Robertson

Well, I certainly didn't envisage writing about Andy Robertson this month.

The modern-day Liverpool legend has been usurped by Milos Kerkez on Merseyside, and with six months remaining on his contract, Tottenham, desperate to sign every left-back in the world, are aiming to get ahead of the pack by offering the Reds a sum for his services.

While any transfer fee would be small, Robertson's healthy salary at Anfield means the 31-year-old could emerge as one of the club's highest-earners, should a deal go through this month.

The proposed move has divided supporters, with benefits and caveats already widely discussed. Here are the winners and losers from Tottenham signing Robertson before the January transfer deadline.

Winners and losers from Tottenham signing Andy Robertson

Winner #1: Destiny Udogie

We were supplied with more proof on Tuesday night that Destiny Udogie makes a hell of a difference when he's fit and firing. Unfortunately for Spurs, the imposing Italian full-back is seldom that.

Udogie has missed 27 games for club and country since the start of the 2024/25 campaign with five different injuries. Knee and hamstring issues have hindered his development into one of Europe's standout left-backs. Thomas Frank has been without him for 14 games this season.

While Robertson is direct competition, he isn't a usurper. The Scot is not the driving force he once was, but is a steady Premier League left-back who can offer Udogie respite. He should be a better fit for Frank than Djed Spence, who now looks awkward on his wrong side, given the demands of the manager.

Frank needs a left-footed left-back. It's that simple. While Udogie will remain first-choice, Frank shouldn't feel the need to overuse the brittle Italian. Preserving the former Udinese starlet will be key during the second half of the season.

Loser #1: João Souza

Robertson won't be the first left-back Spurs have added to their ranks this summer. Earlier in the week, the club finally announced the arrival of teenager João Souza from Santos.

Souza is an unknown commodity. We can all watch the compilations and highlight packages to get a sense of the kind of defender he is, but we don't have a clue how he'll acclimatise and adjust to a wildly different environment.

The addition of Robertson may serve to benefit Souza, easing the pressure on him to settle right away. However, given our transfer needs elsewhere, signing another left-back almost immediately after confirming Souza's arrival isn't exactly the biggest endorsement of the teenager. Perhaps we merely needed a replacement for Ben Davies.

The club may not think he's ready for the jump, and they may be right. It's not necessarily a bad thing, but you might wonder why we signed Souza in the first place.

Winner #2: Thomas Frank

There's a genuine possibility that by the time Robertson is signed, Frank is no longer Tottenham manager. Whether that changes the club's plans, who knows? Nevertheless, I think Spurs' pursuit of the 31-year-old suggests they're still thinking about the incumbent in the dugout.

I see Robertson as more of an 'intangibles' signing. As I've noted, he's not the full-back he once was. While still an excellent crosser, he's never been particularly intricate in the build-up phase. His waning athleticism may limit his impact in the final third, too.

However, the current squad needs a Robertson-like figure. A two-time Premier League champion, Robertson is capable of elevating standards and holding teammates to account. The "winning mentality" aspect I buy into less, because there are plenty of title and trophy winners in our dressing room already. Randal Kolo Muani has won league titles, but he's not exactly brought about a culture shift.

It's Robertson's character that renders him a useful addition. Concerns over tactical fit and physical decline are fair, but the 31-year-old will provide a young and occasionally immature dressing room with added grit, resolve and experience. Intangibles matter, folks!

Loser #2: Transfer priorities

Similar to the Conor Gallagher deal, I quite like it. But, if we fail to bring in a passer in midfield and boost our attacking depth chart, then this transfer window would've been incredibly peculiar from a strategic perspective.

Spurs are down two wingers since the first day of the new year. After selling Brennan Johnson to Crystal Palace, Mohammed Kudus suffered a thigh injury that's set to keep him out until March. That has left Wilson Odobert has our starting right-winger, and unless Kolo Muani discovers some hidden motivation from underneath his bed, the former Burnley man is currently the only useful option at Frank's disposal.

We've turned to Spence to supply cover on the opposite side, while Mathys Tel is disgruntled. The return of Dominic Solanke is huge, but Frank only has five players (including full-back Spence) to cover three forward positions until Kudus, Dejan Kulusevski and Richarlison return. We're setting ourselves up for failure by not adding to our attacking ranks.

In midfield, the issue has been glaring since day one. Frank has an infinite number of eights but no one who excels as the midfield distributor at the base of midfield. Yves Bissouma is probably the best, but he only made his first appearance of the season last week!

We thought our priorities were clear heading into the window, but with just a few days until the deadline, those gaping voids in Frank's squad remain.

Winner #3: Micky van de Ven

Micky van de Ven is contracted at Spurs until 2029. He may be hesitant to sign a new deal, and understandably so, but the club has plenty of leverage to fight off potential buyers this summer.

There's talk of Liverpool making a move, and Robertson's arrival would at least give Micky a taste of Merseyside. Moreover, discussions with the Reds for the experienced Scot could ease relations if the champions decide to push hard for the Lilywhite's superhero defender anytime soon.

For us, that's not particularly good news. Van de Ven, though, once said it was his "dream" to play at Anfield, and he generally seems smitten by the club as a whole. If the second half of Tottenham's season is as dire as the first, the defender may consider a departure, and if Liverpool start lurking, we may be in for a summer saga.

Loser #3: Daniel Levy

I did warn supporters to be careful what they wished for after the departure of executive chairman Daniel Levy sparked widespread joy.

We all lapped up the "ambition" cries from the new-look board in the wake of Levy's exit, and the addition of Xavi Simons for big wages seemed to signal a shift in approach. However, our direction since has appeared confused and panicked. The ambition so far looks misguided.

Curious squad planning remains an issue, and Levy must be fearing that the frugality of his reign will soon be compromised by overzealous spending. If Spurs are to reach the so-called 'next level', breaking Levy's limited wage structure is a necessity. However, the club must only be willing to breach financial thresholds for the right players.

By making Conor Gallagher and Andy Robertson two of our highest earners, ENIC 2.0 may believe they're appeasing supporters, but the overall strategy still comes across as muddled and short-termist. These aren't players you break wage structures for, and the move for Robertson certainly isn't one the ex-chairman would've sanctioned.