Recapping Roma's Transfer Market: New Expectations, Missed Chances and What's Next

We'll spare you the drawn-out Moby Dick analogy, but needless to say, Tiago Pinto didn't manage to land his white whale. The worst kept secret in all of European football was Roma's dogged pursuit of a defensive midfielder. From Florian Grillitsch to Denis Zakaria to Boubacar Kamara, Roma had no shortage of options to shore up their midfield. There was just one problem. An Amadou Diawara-sized problem to be exact.

Through no fault of his own, Tiago Pinto spent the dying hours of the transfer market in a fruitless attempt to find a suitable (or acceptable, to be more apt) team for Diawara. With his €2.5 million salary weighing the club down, Pinto had no wiggle room in the transfer budget to satiate José Mourinho's much-publicized thirst for a defensive midfielder.

Still, despite Diawara's intransigence, Pinto did manage to secure two incredibly useful assets: midfielder Sérgio Oliveira and super-utility man Ainsley Maitland-Niles. With both new acquisitions hitting the ground running, Roma are certainly in better shape than they were a month ago.

And now that transfer season is done and dusted, we assembled the crew (well, part of it anyway) to discuss Roma's new additions and what comes next.

Enjoy and please share your thoughts in the comment section!

Sérgio Oliveira: The Missing Piece?

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Our earliest glimpses of Sérgio have been sensational, but what aspect of his game excites you most?

ssciavillo: I must admit that I haven’t been able to watch Oliveira as closely as I’d like so far thanks to work and baby preparations, so I’ll be looking forward to sitting down on Saturday morning and focusing on Sergio. However, from what I’ve seen during my multitasking, I like his coolness on the ball and head for the game in the midfield. He really adds a different dimension to Roma’s midfield.

JonAS: Yaaaay, baby preparations! Baby shower! Gender reveal party! Blue cake, pink cake! To answer the question at hand: His man bun. So sexy. And his calmness on the ball. He looks smarter and thinks faster than Cristante too.

Bren: Steven, what’s more important: your first child or Roma’s new midfielder?

To be quite frank, I knew very little of him prior to this signing–apart from his name. So in that respect, I’ve been impressed by everything. You can just tell by the way he carries himself and how he interacts with his teammates, this guy just knows how to play football. But in terms of specifics, I’ve been incredibly impressed by his playmaking ability, which will not only help Roma’s attack create better chances, it should take some of the pressure of Lorenzo Pellegrini.

Dude is just a footballer, straight up. And I love it.

He’s not likely to sustain this pace, but where do you see him fitting in once Roma’s midfield is back to full capacity?

ssciavillo: Based on what we’ve seen so far, I expect Oliveira to be a regular starter in Roma’s three-man midfield in the 3-5-2, along with Pellegrini. I think he’s going to take minutes from both Jordan Veretout and Bryan Cristante as those two battle it out for the third starting spot. All four will get plenty of minutes, but I see Lolo and Sergio playing the most.

JonAS: Yeah, he’s already a Mou favorite and Pellegrini is also a certainty. So in the current lineup or the 4-2-3-1 one of Cristante and Veretout will be doomed to sit on the bench when both are healthy. Once the DM arrives, I think it’s DM - Oliveira - Pellegrini with Cristante as the joker. And Veretout will be sacrificed for a cash injection.

Photo by Giuseppe Maffia/NurPhoto via Getty Images

Bren: I was tempted to say he’ll be a piece of the puzzle–albeit a big one–but you’re spot on Jonas—he has Mourinho’s ear already, so I think he’s going to be a lock week-in-week-out starter. I think some combination of Sérgio, Pellegrini, and Mkhitaryan should keep the supply chain moving—now only if he could do the same thing with used cars.

Despite his terrific start, is there anything about this transfer that worries you? Is there any scenario in which Roma doesn’t exercise the option on his deal?

ssciavillo: I mean the only thing that could worry me from a Roma perspective is that he’ll be 30 years old if Roma exercises his option. So, he may have some issues toward the end of his contract with the club. However, I think at €12 million—if he plays anywhere near the level we’ve seen so far—then a permanent deal seems like a no-brainer and a formality.

JonAS: Well, he could be really good for six months and sign his well-earned definitive contract at Roma. And after Summer he could suddenly turn into a Santon or Fazio. Or a serious injury before June. But as long as Mourinho is here, it looks like he’ll remain an important part of the team.

Bren: Yup, that was my only worry as well: his age. We’ve seen it far too many times. A player in his late 20s or early 30s has a bright start and quickly fades away, so I’d be cautious going beyond three years with him, but he can at least replicate what Mkhitaryan has done into his early 30s, those fears will dissipate.

Ainsley Maitland-Niles: Value in Versatility

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He hasn’t had quite the same start as Sérgio, but what have you liked about AMN so far?

ssciavillo: I think the best thing about the Englishman so far is that he hasn’t looked out of place. The transition from league to league usually takes some time, but Maitland-Niles has looked like he belongs so far. I also like the fact that he’s already started on both flanks, which gives Mourinho more options down the stretch.

JonAS: His first game vs Juventus was decent, after being only one day in Rome. That alone impressed me. He didn’t really feel nervous or uneasy, he was ready to do his job. No nonsense. He’s healthy, can play multiple positions. A typical January move to tweak the squad. He basically replaces three persons who left: Calafiori, Reynolds, and Villar. Money well spent.

Bren: He didn’t make much of an impression in the Juve game, you’re right about that Jonas. Broadly speaking, he looks like a tremendous athlete, one who can definitely run with any attacker in the league, which will help him float from position to position. He showed some great forward bursts in the final match before the break. After speaking with our Arsenal colleagues, the impression I got was that he’s basically a Florenzi-type: not really great at one area—not to the point where he’ll displace anyone in the lineup—but I can easily see him playing, say, 80% of the available minutes down the stretch.

It may be too soon to tell, but what’s his ideal position/role under Mourinho for the next six months?

ssciavillo: I think ideally he gives Mourinho a viable option to spell Rick Karsdorp at right-back so the Dutchman doesn’t break down. I mean that’s why he was brought to the capital. Other than that, I think his versatility can be a big asset on a roster that isn’t the deepest.

JonAS: Just be ready when Karsdorp, Cristante, or Viña go down.

Bren: Haha, sad but true, Jonas. I think most of his time will be spent at right-back to keep Karsdorp fresh, but I’m really curious to see how he’d do in defensive midfield. I’m not entirely sure what his ideal role is, but I think he’s going to play an awful lot over the next few months.

Roma and Arsenal sort of left the final terms of this deal up in the air, so what must Maitland-Niles do to convince Mourinho and Pinto to keep him long-term? And at what price would you feel comfortable doing so?

ssciavillo: I think Maitland-Niles has to prove in the next six months that he has the goods to be a starting-caliber Serie A player. Mourinho always compares Roma’s roster to the other big sides and points out “starters” that those teams have as depth. Roma has to continue to build a roster with two starting-caliber options at every position, even if that’s 6-7 versatile players like AMN that can start at more than one position. The price tag could be an obstacle if AMN plays that well during his loan though. Without a set option or obligation to buy, Pinto might find himself between a rock and a hard place in negotiating with Arsenal. I don’t know what Roma’s budget will be this summer, but I’d find it hard to stomach spending more than €15 million on a right-back if Rick Karsdorp is still the starter.

JonAS: Yeah both teams can’t be winners in the long run. If AMN disappoints, Roma won’t buy him and Arsenal are still stuck with him in the summer. If AMN excels, Arsenal have the upper hand during negotiations and Roma will need to pay more, thus going for other options. I think AMN’s goal is to win something (Coppa, Conference League) while at Roma and end in the best possible position in Serie A. Then we’ll see how it goes but Roma better not waste their time with Arsenal for a second summer in a row.

Bren: Well, he’s 24, so there is still a little room left for growth. If he can improve the finer points of his game–passing, and playmaking–he could play his way into a permanent transfer. At its most basic, he just needs to be consistent and dependable, and if they can lock him down for anything less than €18 million, I think that’s money well spent given his age and versatility. He’ll never be the most exciting player in the world, but he can provide tremendous value to a club like Roma.

Missed Moves & Summer Priorities

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Will Roma regret not signing a genuine defensive midfielder this winter? Why or why not?

Bren: I don’t think so. Having or not having a legitimate defensive midfielder likely won’t mean the difference between the Champions League and the Europa League. I mean, it would have been nice to get one, but I’m confident that Mourinho can continue to wing it (for lack of a better word) for the next few months. They definitely need one in the long-term, but I don’t think their inability to land a DM this month will doom the remainder of the season. There are enough in-house options or tactical tweaks to paper over the cracks.

ssciavillo: I agree with bren here that in the short term a true defensive midfielder probably wouldn’t have been enough to get them into the Champions League this season. However, it likely will be priority number 1 this coming summer and the position that will be vital in seeing the Giallorossi show considerable improvement from year 1 to year 2 of Mourinho’s reign.

JonAS: Yeah, don’t need to panic buy now and enter Summer with less cash to spend and another redundant player. I genuinely believe Pinto made a move for Zakaria but why would he choose Roma if he had a lot of other suitors?

However, if they had spent the time and effort they put in AMN and Oliveira (the latter is already a stud in Rome though, not denying that) in Kamara or Grillitisch instead, perhaps they would have made a chance. And we got a more defensive-minded midfielder than Oliveira for Mourinho’s master plan. Still hoping Darboe will finally breakthrough though. And for now, I’m more than happy with Oliveira.

Okay, regardless of what you just said, which DM should they focus their efforts on this summer?

Bren: Well, Florian Grillitsch and Boubacar Kamara are each free agents, so the conversation necessarily needs to begin there. The question, then, is what do you prefer: Grillitsch’s experience or Kamara’s promise? I tend to lean towards Grillitsch because he’s already a finished product and you can drop him right into the lineup and not skip a beat, though Kamara is an incredibly exciting prospect.

ssciavillo: Kamara was such an intriguing name when he was linked to Roma this summer because he’s a high ceiling player with plenty of experience already. However, that ship has sailed and he’ll be PL bound come July. Money talks. I don’t have a name in mind at the moment and even if I did, I’m sure Pinto will end up signing someone who isn’t even on our radar yet. So, I’d keep an eye out for a new name come summer that we didn’t see coming.

JonAS: I see Xhaka’s name popping up again. There’s no love lost between him and Mou it seems. I also think Kamara is bound to go to a bigger, badder club than Roma. I have a feeling Grillitisch could turn into a Radja/Strootman/Perrotta sort of buy. A really good piece of business.

Witsel is a cheap option since he’s a free agent but on the wrong side of his 30s. Why not try for Hojberg from Tottenham again? Also a big fan of Nandez from Cagliari. It depends how quickly we get rid of the likes of Diawara, Villar, Olsen, Florenzi, Kluivert, etc. So Pinto can make his early moves.

Henrik Mkhitaryan’s deal expires in six months, should they sign him to a long-term deal, or is it time to cut bait?

Bren: Oof, that’s a tough ask. This season has shown us two things: he’s still damn good but he’s also on the wrong side of 30, so it all depends on what kind of contract he’s seeking. If he’s cool with a two-year deal, then absolutely, sign him up but anything beyond that is risky. We’ve seen how temperamental those 33-year-old legs can be.

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ssciavillo: Very tough call given all that Mkhi has given to Roma over the past couple of seasons. If he’s willing to take a one-year deal as a rotation player then it could be a solid move. It’d be a great way to keep him fresh and impactful while giving plenty of minutes to the young core of attacking players. But, if he’s looking for too many years then it’s sadly time to move on.

JonAS: Agreed with ssciavillo. Give him one more year and next season Roma can once again evaluate things. He’s a more than a decent player and he looks reborn in his new role in midfield. But Roma should be done with handing out long contracts like they are Skittles. If Micky wants 2 seasons instead, then maybe it’s time to part ways. Or a 1+1 option if he reaches certain numbers/appearances.

Apart from DM, what other area(s) should they focus on this summer?

Bren: Hmm, that’s a tough question because that is really the only glaring area of need. They will need some sort of hybrid winger/striker to support Tammy Abraham and possibly push Eldor Shomurodov to up his game. We could also add center-back to the list depending on how they feel about Chris Smalling potentially entering the final year of his deal.

ssciavillo: I think right-back may have to be addressed depending on what happens with Maitland-Niles and Reynolds. The former has no clause for purchase in his loan and we know Arsenal aren’t fun to deal with. The latter needs to prove that he belongs while out on loan. I also agree on a winger with Perez probably on the way out, especially if Mourinho wants to go back to a 4-2-3-1. Lastly, I’d say we will probably move for a center back because one of the center backs will probably be sold. I could see Ibanez moving on a big-money deal or the team moving on from Smalling if a Premier League side comes calling.

JonAS: Yeah, AMN is only a dry loan and I don’t see him staying after June, only if he really (like REALLY) explodes and turns into Maicon 2.0. But then Arsenal will ask for more money. I don’t have high hopes for Reynolds so far, so a RB is necessary as deputy to Karsdorp. Perez, Veretout, Fuzato could leave and thus need to be replaced. Will SES stay or leave? Is Eldor disappointed after his first year and does he want out? What if a monster bid comes in for Zaniolo or Ibanez? And will we ever see the real Spinazzola back? There are just so many questions, I fear we’ll need to wait and see week after week how the mercato evolves.

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We have a few months before we have to fret about Pinto's next move, but what should the club prioritize come summer? Give us your thoughts!