One of the trickiest scenarios for a club is when a star player enters the last year of their contract. With the threat they might leave on a free transfer in 12 months' time, the leverage in negotiations moves toward the player and their agent.
Broadly speaking, a club is left with three choices: persuade the player to sign a new deal, play the high-risk strategy of keeping that player and hoping talks progress, or accept defeat and sound out the market to find a suitor -- though any interested parties will often be able to negotiate a lower transfer fee because of the expiring contract.
As this season comes to an end, there are some world-class players who could face such a predicament soon. Real Madrid's Vinicius Junior, Arsenal's Bukayo Saka and Paris Saint-Germain's Marquinhos -- as well as Rafael Leao after recent developments with AC Milan over his future -- are more than likely to sign new deals in the coming weeks, while West Ham should exercise a one-year extension option in £100m-rated midfielder Declan Rice's contract until 2025. But there are still a host of top names who could be snapped up.
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Harry Kane, 29, centre-forward, Tottenham Hotspur
The long-term future of the record-breaking Spurs and England centre-forward is arguably the most heavily anticipated decision in world football. Kane's next contract will carry him toward the tail end of his career, and he wants to ensure that he has some silverware when it finishes.
Whether he chooses to further cement his legendary status at Spurs, or succumb to the lure of Chelsea or Manchester United (both are reported to hold an interest, with prospects of a better financial deal if not necessarily trophies), or even move abroad to Bayern Munich or Real Madrid, he certainly has options.
However, Kane's contract is just one of many interlinked predicaments Spurs' omnipotent chairman Daniel Levy has to grapple with. Finding a head coach who matches the striker's expectations is another.
Marcus Rashford, 25, forward, Manchester United
As much as the Manchester United fans are waiting impatiently to see one of their most important players commit to a new deal, time is less of an issue here. There's little to suggest that Rashford is keen to move away from Old Trafford -- he's an academy graduate with a sky-high standing at the club -- and the end game appears to be securing an improved contract that could see him become the squad's best-paid player.
With takeover talks set to reach a conclusive phase at Old Trafford, getting the club's top scorer to secure his long-term future would be a pleasant, early statement of intent for the new ownership to announce its arrival. Sure, the sooner the better, but even if the negotiations were to linger long beyond the summer, one would expect United to offer Rashford as good a sporting and financial project as anyone.
Mason Mount, 24, attacking midfielder, Chelsea
On the back of the recent chaos at 11th-placed Chelsea and a season affected by injury, it's hard to gauge how much the England international is appreciated at Stamford Bridge. With a plethora of new teammates who also thrive in the attacking half and RB Leipzig's Christopher Nkunku set to arrive for €70m this summer, the prospect of Mount being a first-choice option for next season looks unlikely.
While Chelsea face a summer of serious squad trimming after spending over €600m in two transfer windows, the homegrown Mount is ideally a player they would like to keep in order to abide by Premier League rules that cap a squad to 17 foreign stars. But given that the 24-year-old's departure would command a significant fee, and with the player having no guarantees of being more than a useful squad player, a move seems the probable outcome. Liverpool, Arsenal and Newcastle have all been linked.
Christian Pulisic, 24, attacking midfielder/winger, Chelsea
Much in the same vein as Mount, the United States international has a decision to make. Though adverse form and injuries have played their part this season, Pulisic runs the risk of dropping further down the attacking pecking order after Chelsea's extravagant spending spree.
One mitigating factor for the 24-year-old could be his ability to feature as an out-and-out winger on either side (something the squad doesn't possess much of already), which might present the incoming head coach with some options. But Pulisic is not considered indispensable and doesn't appear happy to play a bit-part role, either, so it's likely he will move on.
James Maddison, 26, attacking midfielder, Leicester City
Embroiled in a relegation fight, Leicester might end up paying the ultimate price for failing to extend the contracts of their top performers (defender Caglar Soyuncu has already agreed to sign for Atletico Madrid, while midfielder Youri Tielemans is also set to leave on a free in the summer).
Even if Leicester do beat the drop, the prospect of keeping Maddison beyond the last year of his contract is slim. The England international is a technically gifted attacking midfielder who can strike a free kick and poses a great goal threat, so there will be plenty of interest from clubs fighting for European places like Tottenham and Newcastle.
Dani Olmo, 25, attacking midfielder/winger, RB Leipzig
Four seasons into his Bundesliga career, one might have expected the former Barcelona youth team winger to cut more of a dominant figure for club and country. Now 25, there's still a feeling that there is more to come from Olmo, and while the Spain international's ability to take on defenders, his excellent turn of pace and inclination to shoot from distance are often in evidence, he needs to step up in his prime.
Leipzig have reportedly offered the €29m signing from Dinamo Zagreb a contract extension, but the top clubs in England and Spain are keeping close tabs on developments.
Sergej Milinkovic-Savic, 28, central midfielder, Lazio
Few players have been subjected to more transfer speculation over the past few years than the Serbia midfielder. Yet, in his eighth season at Lazio -- with more than 300 appearances -- Milinkovic-Savic is still with the club.
What makes the 28-year-old such an attractive player is his unique skill set of physical power, aerial dominance, wonderful off-the-ball movement, fine passing, an outstanding knack for timing his attacking runs and expert finishing. In other words, pretty much the ideal profile for a box-to-box midfielder.
While Lazio are reported to be preparing an improved contract to keep the club legend in Rome, the midfielder has sent mixed signals and his agent claims his client's future won't be discussed until the end of the season. Either way, an array of big clubs like Arsenal, Manchester United, Real Madrid, Newcastle and Juventus are sure to enter the race to sign him.
Hirving Lozano, 27, winger, Napoli
Despite being crowned a Serie A champion last week, there are signs that the Mexico winger could leave Napoli. Having arrived in the summer of 2019 for a then-club-record fee of €45m from PSV, "Chucky" is yet to command the status of an undisputed regular. Indeed, the reigning sentiment in Napoli is that as much as he's a valued squad member with match-winning abilities, he still doesn't make enough of a continued impact to justify his reported €7.2m yearly salary.
While recent links to Liverpool are premature, several Premier League clubs would reportedly be interested in the event that Napoli were ready to negotiate a transfer in the range of €18m to €25m.
Alessandro Bastoni, 24, centre-back, Inter
The Italy international has seemed to get better every year after making his debut for Inter in 2019. Left-footed, safe in possession, strong in the air and assertive in duels when he needs to be, it's no wonder Bastoni is on the short list of several elite European clubs.
Though he's almost exclusively featured to the left of a back three, the defender's intelligent and calm style should see him succeed with one central defensive partner too. No matter how the season ends for Inter, they'll need to come up with something special to keep their outstanding defender, and with Milan Skriniar heading to join PSG on a free transfer, there's a major defensive rebuilding job to be done in the summer.