Oliver Skipp's time at Spurs ending? His departure would continue unfavorable trends

Oliver Skipp's time at Tottenham may be coming to an end. It's hard to believe that the plucky academy player could leave the club permanently, but it does seem to be the end of his Spurs tenure. The arrivals of new midfield signings plus the possible integration of other academy players with more hype around them are surely spelling trouble. Skipp's time at Tottenham has not been easy, with managers coming and going, new tactical philosophies, and football directors willing to cash in on more signings. Skipp could be the next player on his way out.

Reports from Football League World suggest that Leeds United are preparing a bid for Skipp to bolster their promotion charge in the Championship. Leeds lost in the playoff to Southampton, and recently sold highly-rated teenage midfielder Archie Gray, who looks to be heading into the first team almost immediately after joining Spurs for £40 million. Skipp, 23, is looking for more consistent minutes after he's played a bit part role under Ange Postecoglou.

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Oliver Skipp could move to Leeds United, furthering casting doubt on Spurs' academy

There was hope Skipp could revert to a fullback role in the absence of Destiny Udogie when the Italian left-back suffered a quadriceps injury. Emerson Royal was initially deputized as a stand-in left-back, but his repeated calamities while trying to play the inverted role forced Postecoglou to rethink. Skipp played most of the second half of the 4-2 loss at Liverpool at left-back and showed some flashes of brilliance, but he was never seen as the long-term solution. Micky van de Ven would finish out the season at left-back and do so quite brilliantly.

Skipp's time at Spurs is reflective of trends under previous managers: they don't give Tottenham academy players a clear path into first-team football. Sometimes the players aren't at the level needed, but other times it is down to managerial preferences. Skipp, in many ways, is following a path similar to that of Harry Winks, another Tottenham academy player who sparkled at times but could not carve out a permanent role under several managers. Winks went on a few disappointing loans before being sold to Leicester, where he became a key piece to the Foxes' promotion back to the top flight. Skipp's career seems to be heading in the same direction. He hasn't been able to crack the Spurs bench at times, and Postecoglou made it known he preferred Rodrigo Bentancur, Yves Bissouma, or Pierre-Emile Hojbjerg – even as substitutions.

The arrivals of Lucas Bergvall and Gray make it even harder for Skipp to find a role in the first team. Perhaps Spurs should take the money and reinvest in a key transfer, as the shopping is still not done. There are also prospects like Jamie Donley and Mikey Moore, midfielders with an incredible amount of hype after dazzling with the U-21s for club and country. Moore has been compared to some legends of the game, but his full potential isn't clear yet. However, even their future at Tottenham is murky with how many senior midfielders there are, and none have departed the club yet.

Skipp might be better off leaving if he wants more consistent game time. However, depth will be important for the next season, especially as injuries pile up because we know they will. If he's not up to the Postecoglou style, it may be best to let him join a promotion-favorite in Leeds. If the England international does move, it will show the academy still needs revamping so players can integrate faster. Chelsea and the Manchester giants are good examples of how having a strong academy pipeline can be incredibly beneficial.

Skipp impressed after a very fruitful loan with Norwich in the 2020-21 season and started decently when he returned to N17 in 21-22, but managers lost faith in him. He had some good moments, like his long-distance rocket against Chelsea in 2022-23. Those have been few and far between, though.

He is young enough that his career isn't even close to over. He still has time to refine his game and reach the potential some scouts believe he has. The question will be whether he will do it in a Tottenham kit or another.