Allowing players to run into the final year of their contract is a dangerous game for elite clubs. Watching a star player leave hurts, but watching a star player leave for nothing hurts many times more.
For this reason, it is hugely surprising that Manchester United has allowed a ridiculous 12 players to enter the final year of their contract this summer (Andreas Pereira and James Wilson don't feature on this list as we are focusing on first team players).
This mismanagement at Old Trafford is almost laughable and it seems that Manchester United have not learned from the most high profile contract mistake they made - Paul Pogba. The Frenchman moved to Juventus for nothing in 2012 before United embarrassingly brought him back for a then world record fee of €105 million.
To compare, Manchester United's 12 players with less than a year left on their contract is more than Chelsea (5 first team players, 3 reserve/youth players), Liverpool (6 first team players, 1 youth player), Arsenal (5 first team players, 1 reserve player), Man City (2 first team players, 2 reserve/youth players), and Spurs (4 first team players, 1 reserve player).
An expiring contract grants players the power to utilize the Bosman rule, a law designed to protect the rights of players and allow them to choose if they would like to move clubs without any consequences to their current salary or treatment as an employee of their current club. Players can open discussions with new teams once they have less than 6 months left on their contract.
There has been numerous high profile transfers down the years because of this rule including Manchester United's very own Paul Pogba as noted earlier. Will any of the players on this list exert their right to talk to other clubs and leave Old Trafford without a transfer fee next summer?
Listed below, in ascending order according to market value, are the 10 Manchester United players whose contract expires in 2019.
Contract data is provided courtesy of Transfer Markt and is correct at the time of writing.
#10 Ashley Young
Market Value: €7 million
Last Contract Extention: March 19, 2018
Contract Expiry: June 30, 2019
Age: 33
A constant presence in the Manchester United back line over the past few seasons, Ashley Young has proved hugely reliable since moving from midfield to fullback. The England international made 38 appearances in all competitions for United last season and is expected to play as the first-choice left back in this coming campaign.
His contract was initially due to expire in June 2018, however, Manchester United triggered an extra 12-month clause which means his contract now expires in June 2019. There are no further clauses in his contract meaning Manchester United will need to negotiate a new deal if they want the 33-year-old to remain at Old Trafford longer than one more season.
Verdict
Ashely Young has proven indispensable to United over the past few seasons and still has plenty left in his tank. While he is no longer a spring chicken, he deserves another contract at the very least as a squad player and as an influence on younger players.
#9 Antonio Valencia
Market Value: €8 million
Last Contract Extention: May 26, 2017
Contract Expiry: June 30, 2019 (one year option)
Age: 33
Another everpresent in the United defense, Antonio Valencia has worn the captain's armband for the Red Devils on several occasions. The Ecuadorian is another player who moved from an attacking wing position to a fullback role and has excelled over the past few years. He played 39 times last season and is expected to have a big role in the upcoming campaign.
Valencia last signed a contract in May of last year after he was voted Manchester United's Player's Player of the Year. While his deal expires next summer, there is a clause which Manchester United can trigger to keep Valencia at the club for a further 12 months.
Verdict
The right fullback has proven an excellent and reliable player for Manchester United over the past few seasons. Although he will be 34 by next summer, United should trigger the year extension clause and keep him at Old Trafford.
#8 Matteo Darmian
Market Value: €10 million
Last Contract Extention: July 11, 2015
Contract Expiry: June 30, 2019 (one year option)
Age: 28
Matteo Darmian arrived at Old Trafford in 2015 as one of the most highly rated fullbacks in the world. However, the Italian has struggled to get consistent playing time for the Red Devils and has made only 54 Premier League appearances in three seasons. Last season, Damian played only eight times in the league.
His exclusion from the team for most of last season has led to speculation that the 28-year-old would move back to Italy this summer. With a deal yet to materialize, United must proceed with caution or risk losing the €18 million they initially invested.
Verdict
While Damian has a clause which could trigger an additional year on his contract, it seems like the right time for United to cut their losses on the Italian. With a handful of Serie A clubs interested in his services, we are likely to see Damian depart Old Trafford this summer.
#7 Luke Shaw
Market Value: €15 million
Last Contract Extention: July 17, 2018
Contract Expiry: June 30, 2019
Age: 23
Luke Shaw has been extremely unlucky since moving to Old Trafford in 2014. The left-back endured a horrific leg break and has struggled to regain fitness since. Mourinho's well-documented comments about the player in the media, calling him out on several occasions for poor performances or lack of fitness, has led to speculation about the full back's future at Old Trafford.
Manchester United triggered a 12-month extension written in Shaw's contract this summer to keep him at the club until 2019. There has been many reports and stories in the media claiming Shaw could potentially find a new contract offer on the table if he impresses Mourinho during this coming season.
Verdict
Luke Shaw has been an unfortunate story at Old Trafford over the last few years. He arrived with bags of potential and at just 23 years old could still become an exceptional player. Manchester United should keep faith in the former Southampton man and extend his contract to tie him to the club for the foreseeable future.
#6 Chris Smalling
Market Value: €18 million
Last Contract Extention: April 21, 2015
Contract Expiry: June 30, 2019
Age: 28
Chris Smalling is almost an anomaly for Manchester United. The center-back is often criticized for his performances with claims he is not good enough to play for Manchester United. However, the 28-year-old has played consistently for the Red Devils and been a part of one of the stingiest defenses in Europe over the past two seasons.
His last contract extension came way back in 2105 and doesn't feature the option for a 12-month extension. Therefore, Manchester United will need to negotiate a new full contract with the England international if they wish to keep him at the club beyond next summer.
Verdict
At 28, Smalling should be entering the peak of his career. While he is prone to mistakes, he has also proved capable of playing at the highest standard for United. Allowing him to leave on a free could prove a big mistake and rather Manchester United should extend his contract and then seek a good transfer fee should they wish to replace him in the future.
#5 Phil Jones
Market Value: €20 million
Last Contract Extention: June 29, 2015
Contract Expiry: June 30, 2019
Age: 26
Yes, another defensive player meaning the whole United backline could be out of contract by next summer. Phil Jones may circle around social media with clips of his hilarious last-ditch defending, but the 26-year-old has proven an excellent asset to the United defense. Having played 23 times in the Premier League last season, it is obvious that Jones remains one of United's main men in the defensive line.
Jones last signed a contract in 2015 and while reports of a new contract were reported last year, pen was not put to paper on a new deal. At just 26, Jones still has many years left in his career and is certainly an asset at the club who should seek to open negotiations as soon as possible.
Verdict
Losing Jones on a free transfer would represent extremely poor contract management by Manchester United. With a market value that has continually increased over the last few seasons, Jones' stock is almost certain to maintain its steady climb over the coming years. United should urgently offer the defender a new deal.
#4 Ander Herrera
Market Value: €30 million
Last Contract Extention: July 1, 2014
Contract Expiry: June 30, 2019
Age: 28
Ander Herrera has been superb for Manchester United since joining in 2014, capturing the Player's Player of the Year award in 2017. The midfielder found competition difficult last season, but still managed 26 appearances in the Premier League. He most certainly still has a lot to offer Man United.
Herrera signed for Manchester United in 2014 after a farcical pursuit of his services the summer before. However, since arriving he has not signed a new contract and we are now left in a situation where he has less than 12 months remaining on his current deal. while there have been rumors of a new contract, nothing has materialized as of yet.
Verdict
The Spanish midfielder is an excellent player who certainly has a future role at Old Trafford. Considering the effort it took to get Herrera in the first place, United should look to extend his current deal as a matter of urgency.
#3 Juan Mata
Market Value: €30 million
Last Contract Extention: Jan 24, 2014
Contract Expiry: June 30, 2019
Age: 30
Juan Mata has enjoyed an excellent four seasons at Old Trafford since his arrival from Chelsea. The Spanish attacking midfielder offers United a unique creativity with his ability to split defenses and play cute through balls. He remains an important first-team player and made 40 appearances for United last season.
Another player signed in 2014 and not given a new contract as of yet, Mata's initial contract was extended by 12 months earlier this year. There has been no further word about whether United will seek to initiate negotiations for a new contract in the near future, but Mata undoubtedly still has a role to play at Old Trafford.
Verdict
While the Spanish maestro is entering his 30s he still has a lot to offer United going forward. Depending on his wage demands, the Red Devils could benefit from his presence off the bench and as a role model for younger players over the coming seasons.
#2 Anthony Martial
Market Value: €65 million
Last Contract Extention: Sept 1, 2015
Contract Expiry: June 30, 2019 (one year option)
Age: 22
Anthony Martial's arrival at Old Trafford was greeted with shock and disbelief at the huge transfer fee involved. However, the Frenchman has shown why United forked out such an extravagant fee for his services with some exceptional performances in the red shirt.
While he is still young and full of potential, Martial has been heavily linked with a move away from United this summer due to disagreements with Mourinho and lack of playing time.
As it stands, Manchester United has an option to trigger a further 12-month clause in Martial's contract and keep him at Old Trafford until 2020. However, triggering this clause and continuing to underuse the Frenchman will only lead to further frustrations and ultimately mean he will walk away for free in two years time.
Verdict
Martial is an outstanding talent with a long career ahead of him. Mourinho should sit down and talk to the young winger, explaining that he will get his chances over the coming season and to reassure him of his future at Old Trafford. Losing the Frenchman could prove to be a monumental error of judgment akin to the Pogba fiasco.
#1 David De Gea
Market Value: €70 million
Last Contract Extention: Sept 11, 2015
Contract Expiry: June 30, 2019 (one year option)
Age: 27
David De Gea has grown from an unsure kid into the best goalkeeper in the world during his time at Old Trafford. The Spanish shot-stopper has been United's best player consistently over the past few seasons, saving the team on countless occasions and deservedly winning countless personal awards.
Rumours linking De Gea with a move to Real Madrid have persisted over the past few transfer windows. However, the 27-year-old signed a new contract in 2015 with a further one year option which United can trigger to extend the contract until 2020.
As one of the best goalkeepers in the world, United are keen to tie De Gea down for a longer period and have reportedly opened negotiations over a new 5-year deal this summer.
Verdict
There is little doubt that De Gea will be offered a new deal in the near future. It is essential that United give the Spaniard whatever he wants to keep him at Old Trafford for many years to come.