Bayern Munich's search for a new winger began a long time ago. They knew it would not be easy either.
The contracts of veteran duo Franck Ribery and Arjen Robben were both due to expire at the end of the 2017-18 season. However, with Kingsley Coman deemed little more than a squad player because of his form and fitness struggles, the pair were given one-year extensions in order to allow Germany's most successful side more time to acquire adequate replacements out wide.
Serge Gnabry returned from loan last summer to bolster Bayern's ranks but they still wanted to sign another winger as part of the succession plan.
Canada's Alphonso Davies, 18, arrived in January and played six games before the end of the season. Bayern had also tried to land another teenager during the winter window but their public pursuit of Chelsea's Callum Hudson-Odoi ended in embarrassing failure.
As a result, Bayern began their 2019-20 campaign with just three wingers: Coman, Gnabry and Davies. Only Coman started the dismal DFL-Supercup loss to Borussia Dortmund a fortnight ago.
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Gnabry was absent with a thigh injury, meaning Thomas Muller played in his place, while Davies began on the bench.
Even when the latter was brought on midway through the second half with Niko Kovac's side trailing to Paco Alcacer's 48th-minute opener, Bayern looked blunt and Dortmund eased to victory adding a second goal through Jadon Sancho just minutes after Davies' introduction.
Gnabry was badly missed on the day. He has been a real success story at Bayern, surpassing expectations following his move to the Allianz Arena from Arsenal.
Initially signed by Werder Bremen, and then permanently by Bayern, he scored 10 league goals on loan at Hoffenheim in 2017-18 and matched that tally last term, after finally getting his chance to shine in Munich.
Coman netted just six times, but injury meant he played just 21 matches – nine fewer than Gnabry. Of course, that came as no surprise. Coman has never managed to feature in more than 23 league games in a single campaign during his entire career because of various ailments.
This should have put further pressure on Bayern's bosses to find a new winger, especially after club president Uli Hoeness and sporting director Hasan Salihamidzic used the media to court Hudson-Odoi in January only for Chelsea to refuse his transfer request. The England international later injured his Achilles tendon, which ruled him out for the remainder of the season.
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With Hudson-Odoi off the market, Bayern turned their attentions to Leroy Sane: a young and exciting winger who would have been as big a coup for Bayern as Robben 10 years previously.
The 23-year-old is considered one of the game's biggest and brightest stars, and has been frustrated by a lack of game time at Manchester City.
However, Bayern's hopes of landing Sane were hindered by Kovac publicly describing the Germany international as his "dream player", which upset chief executive Karl-Heinz Rummenigge, and then completely dashed by the attacker suffering an ACL injury in the Community Shield clash with Liverpool earlier this month that is likely to rule him out until 2020.
That left Bayern in a bind. In fairness, they did manage to sign a winger this week – just not one anything like their previous targets.
Ivan Perisic has arrived from Inter on a season-long loan that also contains a purchase option for €20 million (£18.5m/$22.5m).
He brings Bundesliga experience, having played for Borussia Dortmund and Wolfsburg before moving to Serie A, but is 30 – just five years younger than Robben – and is nothing like either Hudson-Odoi or Sane as a player.
Perisic is a short-term option for a team who should be building for the future.
Coman's persistent injury problems and Davies' inexperience mean that even after signing Perisic, Bayern remain in the market for another winger. Ajax ace Hakim Ziyech, 26, fits the bill in terms of attributes and age, but he has now signed a new deal in Amsterdam after losing patience with Bayern.
"I could have waited for them, yeah. But it felt like the right moment to clarify my situation, both for Ajax and myself," he told AD. "If a club wanted me, they could have made their move."
Of course, signing Perisic on loan means Bayern still have plenty of scope to spend big. As a result, Real Madrid's Gareth Bale and Barcelona duo Philippe Coutinho and Ousmane Dembele have all been linked with the Bavarians, as La Liga's two biggest clubs look to balance their books and finance a Neymar pursuit.
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Bale's proposed move to China may have collapsed but with Blancos boss Zinedine Zidane still planning for the new season without him, the Allianz Arena is a possible destination for the Welshman, if only for the fact that Bayern are one of the few clubs that could afford the 30-year-old.
Dembele, of course, represents a younger, more attractive choice but the acrimonious nature of his Dortmund exit, coupled with disciplinary issues at Barcelona, have provoked questions over his attitude.
Indeed, Bayern legend Lothar Matthaus doubts Dembele would embrace the club's 'Mia San Mia' mindset.
"Dembele is a high-quality football player, but I don't believe in his mentality because I know his story from the last three or four years," Matthaus told ESPN. "He protested to leave Dortmund and then at Barcelona, he came late to training and this is not good for team spirit.
"Gareth Bale is not what Bayern Munich are looking for because of his age. He also has his problems in Real Madrid and he is not the type of player for Bayern Munich to plan for the future."
Bayern's chances of getting Coutinho, meanwhile, depend on whether the Brazilian will be used in any potential Neymar trade and thus leaves the German club waiting on other European giants to do business before they can even make a move themselves.
After the delays with Hudson-Odoi and Sane, this once again reflects poorly on the Bayern bosses, who cannot seem to get deals done quickly.
Ziyech's Eredivisie rival, PSV's Steven Bergwijn, has also been a summer target for Bayern, while RB Leipzig forward Timo Werner has long been linked with a switch to Munich. However, Bayern have yet to submit a bid for either player despite the Bundesliga season starting this weekend.
Perisic, for his part, brings experience to Bayern's wing but he is little more than a stop-gap solution to a problem that the club have been trying to solve for two years.