If you’re anything like me, the most exciting part of the year long campaign is undoubtedly the Transfer Market, and if you’re just like me, you’re rather bummed on the day the Market window slams shut, and secretly counting the days until January 1st in hopes that Milan pick up where they left off in negotiations that didn’t come to fruition or in their ambitious recruiting of talent previously left off their public shortlist.

While January 1st is obviously the beginning of the next month-long transfer window, it is June 30th that player deals are written to structurally expire - thus creating the soccer version of the Unrestricted Free Agent, or the infamous Bosman on July 1st.

Unlike the last few years of the Berlusconi/Galliani ownership tandem - which saw Milan add non-contracted players that were seemingly stopgaps (or so we had hoped at the time) or placeholders for younger talent - this past summer alone the new management group of Leonardo and Maldini added a few notable players on a free transfer including goalkeeper Pepe Reina, wingback Ivan Strinic, and winger Alen Halilovic.

Since I’ve been thinking about this new ‘project’ since the dismissal of former owner Li, and his management team of Fassone, and Mirabelli, and since I can’t contain my excitement for the development of this new new Milan, I’ve decided that here and now will be the best place and time to preview players that could be of heavy interest to AC Milan with contracts set to expire on June 30th, 2019... that probably will be renewed immediately after this article gets posted making this entire dissertation and opinion piece worthless, but I’m going to try anyways.

All figures, dates, terms are listed at www.transfermarkt.com, all opinions are my own.

No. 5

Alan Dzagoev
Central + Left Midfielder
CSKA Moscow
Market Value: 15M EUR

The Bargain

It seems like it was only yesterday where this young Russian midfielder was scoring goals by the bunches and making defenders look silly in the Russian Premier League, where he was named “Best Young Player of the Year” at the age of 18. By following that up with some brilliant Champions League games against Manchester United, Inter Milan, Bayer Leverkusen, Tottenham Hotspur and Real Madrid - who were rumored to have inquired about obtaining his services - mixed in with some dominant performances for the Russian National Team, Dzagoev would help put his name in the thoughts of many a top European club’s technical director.

A technically gifted and incredibly quick player who is not only great with the ball at his feet, but also a dangerous shooter from distance, Dzagoev would slot in nicely in as a vice-Giacomo Bonaventura an alternative option as the left midfielder in Gattuso’s current 4-3-3 formation, but could also feature as an alternate to Calhanoglu as a trequartista in a 4-3-1-2.

No. 4

Moussa Dembele
Central Midfielder
Tottenham Hotspur
Market Value: 18M EUR

The Seamless Fit

One of the two true central midfielders on this list, Dembele has exploded onto the global soccer scene over the last 3 years. A product of the Beerschot program in the Belgian Pro League, he would eventually hone his trade in the Eredivisie with AZ Alkmaar under Louis van Gaal before making the jump to the Premier League with Fulham. It was in England that his career trajectory would shift, as Martin Jol started to experiment in using him in a more creative central midfield position, maximizing his tremendous technical and passing ability, which would become his calling card. Quickly snapped up by Tottenham in 2012, his impact has been felt both on the pitch when he’s dominant, and off the pitch when his recurring injuries forced him to miss long stretches of time.

Dembele might not seem the tallest player, but he is a physically imposing player on the ball which allows him to hold the ball as long as he needs to before using that precise passing ability to pick apart clusters of opponents. Former teammates of his liken his style of play to a vacuum cleaner, in that he is capable of positioning himself deep in the midfield, ‘sucking in all the pressure’ and releases the ball at the right moment. He is also a technically gifted dribbler as well, being content to skip past a defender in the blink of an eye.

While he would seemingly slot in as a player who can give rest to Lucas Biglia at the holding midfielder or regista position, and as player who could play alongside the Argentine, should Gattuso dabble in a 4-2-3-1, he could easily play up in any of the three midfielder positions in a 4-3-3 as well.

No. 3

Angel Di Maria
Right Winger
Paris Saint Germain
Market Value: 40M EUR

The One You Didn’t Know You Wanted

Whats there not to say about the prolific Argentine winger? Between being a star player for Manchester United, Real Madrid, and Paris Saint-Germain, as well as being a full international since the age of 20, he’s won a slew of domestic and international trophies with the 2013-14 Champions League title being the cherry on top.

At the age of 30, el Fideo seemingly hasn’t lost a step and would instantly bring an additional creative dimension to an AC Milan attacking trident as a 4-3-3. While the analysis of his game is focused primarily on his quickness and his high end technical skill, his ability to cross the ball with pace and precision as well as his proficiency in dead ball situations seem to get overlooked. His dribbling is of another level, and coupled with his exceptional agility, acceleration and his left-foot preference, he seems to strike a resemblance to current winger and star Suso. But the difference is his versatility, with capability to be deployed on either wing, as well as an attacking midfielder (which is where he primarily featured under Carlo Ancelloti at Real Madrid) in a 4-3-1-2, or even a 4-4-2.

With 21 goals and 12 assists in 45 appearances across all competitions last season, and already opening his account with 3 goals and 3 assists in 5 games so far in this young season for PSG, he is proven to possess the one thing that Milan have sorely lacked in the last few years: the ability to assist and finish in the final third.

No. 2

Anthony Martial
Left Winger
Manchester United
Market Value: 65M EUR

The Wish List

While Milan have been persistently linked to the young Frenchman all summer, this one has some uncertainty wrapped around it. While it has been reported that there is some type of rift between Martial and head coach Jose Mourinho - presumably the catalyst for all the talk about him leaving this last August - there has been an equal amount of reporting being done as of that Manchester brass has been negotiating an extension with his agents, squashing all the departure talk.

One year removed from an 11 goal and 9 assist campaign across 45 total appearances for the Red Devils, he has yet to make his presence felt in 2018-19. Should he not extend his current deal, you can count on all technical directors from across the European soccer world - including Leonardo and Maldini - will be monitoring his usage and plotting their respective attempts to lure the talented goalscorer to greener (or redder and blacker) pastures.

A player very much in the mold of another Frenchman, Thierry Henry, he possesses great power and acceleration, and couples that with elite technical ability. Capable of blowing right past defenders in a one-on-one situation, he is adept at playing both wings in a 4-3-3 formation. However, he does profess a preference to play as the central striker in a 4-3-3 or a 4-2-3-1. He would fit Milan well, as he is capable of splitting time with Higuain, Cutrone, Calhanoglu and Suso.

No. 1

Adrien Rabiot
Central Midfield
Paris Saint Germain
Market Value: 50M EUR

The Obvious, But Also The Perfect Fit

Ah yes, the one you’ve probably been waiting for. So many inches of newspaper pages have been devoted to the future of the young French midfielder and the interested parties which have so far been reported to include Barcelona, Real Madrid, Manchester United, Liverpool, Juventus, and of course, AC Milan - whereas Leonardo has a unique relationship with both the player and his mother who doubles as his agent dating back to his time with Paris Saint-Germain.

He is only 23 years old and possessing both already developed technical skill that rank him among Europe’s elite in terms of young talent, and a seemingly untapped potential waiting to be exploited. But with that age comes immaturity, a lot of which has gone public - including his self-omission from the eventual World Cup champion France squad because he felt he didn’t belong on Didier Deschamps’ standby list (and he was probably right at the time, but who will question those decisions now).

His skill set is a perfect mesh for Gattuso’s style of play, as Rabiot loves to play the quick pass game out of the defensive end, using his tremendous dribbling skill and precise passes to unlock the opponent’s midfield formations. It was just a couple of years ago where he would have stretches in Ligue 1 where he would complete almost 90% of his passes and averaging more than 60 passes per match, with a majority of them being passes for forward progress. Additionally, he can play deep in his own half to start the breakout, an area where he is known to thrive, sneakily winning a tremendous about of balls back - on the ground and in the air. He would be a perfect candidate to play in the central midfield in a 4-3-3, or play alongside a ball-winner like Kessie or Bakayoko in a 4-2-3-1.

Of course all this talent at a young age does not come without it’s frustrations, as Rabiot has a penchant for taking silly fouls and accumulating cards - although it seems lately as if he is growing out of this trend. Another area of concern is the lack of hesitation in openly vocalizing any complaint about his playing time or usage, coming from both him and his mother, with previous coaches like Carlo Ancelotti and Unai Emery not afraid to glue him to the bench to teach him a lesson.

All things said, the kid wants to play and is very obviously passionate - I guess that’s a French thing - and I couldn’t imagine him not starring in the AC Milan midfield. Professionalism can be taught, and the restructured organization - from Leonardo and Maldini to Gattuso to the entire locker room - seem to be teeming with it.

...and with reports already coming out in today’s Gazzetta dello Sport declaring that Milan might make a move for him in January to ward off any other attempts at other clubs dealing with him on a Bosman, it seems like my list is already obsolete.

Injury Time

Either way, it’s very rare that this level of talent (or really all of these players) reaches the end of their contract in their prime years or with their prime years still ahead of them. And with Financial Fair Play always hanging over the heads of the larger (read: most successful) clubs, acquiring a player like any of the above goes a long way on the field and in the books.

What do you think, did I botch this all up? Who do you think Milan should target on a free transfer? Drop us a line in the comments.