Ranking every signing of Ricky Massara’s Roma tenure

May 29, 2026 Samuel Bannister Features, First Team, Opinion 0

Ricky Massara became arguably Roma’s least popular sporting director since his former superior Monchi during his third stint with the club.

Massara was chosen to replace Florent Ghisolfi last summer, but his first transfer window upon his return was marred by a failure to secure some of coach Gian Piero Gasperini’s top targets.

There were a small handful of success stories, but for every hit there seemed to be a couple of misses, and Gasperini wasn’t afraid to be vocal about not having a strong working relationship with Massara.

Thus, Massara’s time at Roma has come to an end. It’s fair to say he won’t be leaving the best legacy.

Here’s a Giallorossi Yorkshire ranking of all the signings made during Massara’s third spell with the club, as judged on the day of his exit from worst to best.

12. Bryan Zaragoza

In fairness, Zaragoza wasn’t plan A, B or C when it came to Roma’s search for a left winger, but it’s safe to say that as the signing they ended up with, they were left wanting more.

During his six months on loan from Bayern Munich – how he ever ended up there is another question – Zaragoza featured sparsely. His unconvincing first few appearances for the club caused fears over activating a permanent deal, which would have been triggered if he played enough.

But his lack of composure and severe reluctance to use his weak foot proved to be major flaws. In the end, it was more palatable for Roma to pay a penalty fee to return him to Bayern than to buy him outright. And thus, the search for a left winger was prolonged.

11. Leon Bailey

Signed on loan from Aston Villa, Bailey became a Roma flop not because he’s a bad player, but because he wasn’t really needed – and then wasn’t available enough. In other words, the Javier Pastore category.

Injured in his first training session, as Roma out-Roma-ed themselves, Bailey was unable to ever get going.

There are valid questions as to whether Roma even had room for him in the first place. As mentioned, the focus should have been on signing a left-sided winger, but Bailey preferred to play on the right, where Roma were already well-stocked.

Ultimately, the loan was terminated at the halfway point, with Bailey only making 11 appearances for the club and never scoring.

10. Kostas Tsimikas

For a player boasting the pedigree of being at Liverpool for half a decade – granted, not as a regular starter – Roma were left so underwhelmed by Tsimikas that he was rarely used, even when Angeliño was absent for large stretches of the season.

Brought in as a replacement for Anass Salah-Eddine, who grew unsettled after half a year in Italy, Tsimikas should have provided stern competition at left-back, but fell short of expectations.

Roma would not be converting his loan into a permanent move.

9. Robinio Vaz

There were positives and negatives to the move for Vaz when Roma were needing fresh inspiration in attack midway through the season.

On one hand, it was encouraging to see the club looking to the future and investing in a player already showing his potential for Marseille. On the other hand, the size of that investment was – it seems at the moment – too steep.

Roma paid around €25m for Vaz when he was still only 18 and just 22 games into his senior career. With that, came pressure.

Vaz looked a little lightweight in his first few games for the club, but did manage to score his first goal in Italian football before the season was out. Only time will tell if he comes good in the long run.

8. Evan Ferguson

The signing of Ferguson on loan from Brighton was an interesting one. Once billed as a player whose value could skyrocket, he lost his way at Brighton and failed to get back on track with a loan spell at West Ham.

Roma took a chance on the Irishman in a sign they weren’t convinced by Artem Dovbyk anymore, even arranging an option to buy in the region of €40m.

Ferguson began the season as Roma’s starting striker, but he didn’t last long. Fitness issues thwarted his momentum and the last appearance of his loan spell was in January.

As a signing, the move for Ferguson demonstrated a desire to look to the future and see if fading potential could be rekindled. But the option to buy was always too high and the player’s performances just weren’t at the required standard in the end.

7. Lorenzo Venturino

The deal that effectively unlocked Tommaso Baldanzi’s loan exit for Genoa by arriving in return, Venturino came with the blessing of Daniele De Rossi.

Again, it was another example of Roma focusing on the future with their recruitment. However, given that Baldanzi was moving on because of a lack of space, and Venturino plays in a similar position, it was another move whose necessity could be questioned.

During his 10 appearances on loan, the Italy under-21 winger looked steady enough, without really making a major impact in the final third.

The €7m option to buy looked reasonable enough, but the jury was out by the end of the season as to whether it’d be worth activating.

6. Antonio Arena

This is less a judgement of Arena’s three appearances for Roma so far as it is a reflection of his potential – and the club’s decision to take a punt on it.

Just 16 years old when he joined from Pescara, Arena scored with his first touch for Roma in the Coppa Italia defeat to Torino in January.

Whether he adds to his goal tally – and by how many – in the future remains to be seen, but while evidence is limited of his first-team potential at the moment, there is little to complain about Roma bringing in one of the more exciting prospects of Italian football.

5. Jan Ziółkowski

After coming to regret their decision not to keep on a young defender in the shape of Dean Huijsen a couple of years ago, Roma decided to go for another by buying Ziółkowski for €6m from Legia Warsaw.

Aged 20 at the time, Ziółkowski joined with 40 appearances in senior football behind him. However, he struggled to really win over Gasperini after making the move.

Ziółkowski could be sold by Roma after a year, although only time will tell if history repeats itself and they come to regret it. Right now, it feels like the Polish defender doesn’t offer quite enough assurances, but he does have upside.

In terms of the transfer itself, Roma are likely to turn a profit on the youngster.

4. Neil El Aynaoui

El Aynaoui didn’t receive the warmest of welcomes at Roma after quite plainly being an alternative to Richard Ríos, for whom a deal couldn’t be agreed.

After costing up to €25m, there was immediate pressure on El Aynaoui to win over his sceptics. It was a task he couldn’t quite complete convincingly within his first year.

The Moroccan midfielder impressed at the Africa Cup of Nations midway through the season, but struggled to find his best role for Roma. Given the money spent on him, it was underwhelming.

Only 24 when Roma bought him, El Aynaoui has time in front of him to improve, but he wasn’t the kind of signing that raised the level of the team.

3. Daniele Ghilardi

The last of Roma’s summer signings to be given his debut, Ghilardi had to show some patience after his move from Hellas Verona, but became one of the players to improve the most over the course of the season.

From the outset, there was a lot to like about this transfer. Roma were going for a young, promising defender who already had experience in Serie A and had been stepping up year on year in his career so far.

It had been six years since Roma had last bought an Italian defender and they paid a fair price for Ghilardi too. He didn’t cost much more than €10m.

As stated, it took time for his performance levels to settle, and there are still signs of inconsistency, but Ghilardi’s growth has suggested Roma were right to put their faith in him.

2. Wesley

Undoubtedly the pick of the bunch from Roma’s summer signings in 2025, Wesley was a relatively expensive addition for the right-back role, but he proved to be worth it – even if he ended up mainly playing at left-back instead.

Brought to Europe for the first time after breaking through in Brazil with Flamengo, Wesley scored an impressive five goals in his first season with Roma.

The right-back position has been one where various investments over recent years have failed, but the price of up to €30m is one Roma could go on to make a profit on. They will be hoping that’s after enjoying Wesley for a while longer, though.

Wesley has impressed with his endeavour and forward-thinking nature, and has already been linked with clubs with more financial muscle.

Tellingly, Wesley was wanted specifically by Gasperini, who had previously been tipped to take him to Atalanta. Perhaps Massara will regret not being able to grant the coach more of his wishes, given how well this one went.

1. Donyell Malen

If it’s a transformative signing you’re looking for, there can only be one winner. The impact made by Malen after his January arrival from Aston Villa was astonishing.

Malen scored 15 goals over the second half of the season, with 14 of those being in Serie A. No winter signing in the league’s history has ever scored as many in a corresponding timeframe.

The loan deal for Malen was designed to become permanent if Roma qualified for Europe and he played in more than half of their games. All parties were more than glad when those conditions became active to ensure his long-term stay.

Roma desperately needed a striker to improve their efficiency in the final third and Malen took the challenge upon himself, proving how effectively he can play there.

Few transfers in Roma’s recent history – winter or summer – have led to such an instant impact.

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