Just the other day when building my perfect Roma player, I choose Daniele De Rossi to be the brains of the operation. My logic was the following:

While it’s true that De Rossi’s temperament got him in some hot water early in his career, his footballing intelligence came to the forefront as his legs accumulated miles. De Rossi was like a second manager on the pitch for Roma in his later years. He had a great tactical understanding of the game, which was invaluable to the squad. He was also a leader both on and off the pitch. He knew just what to say in the most difficult moments and always faced up to the music when things didn’t go right for Roma and Italy. I wouldn’t be surprised to see DDR using that brain on the Roma touchline one day.

With his interview released by Sky Sport on Saturday, the recently retired Roma legend confirmed my selection. De Rossi finally admitted that he will get into coaching with the ambition of one day leading the Giallorossi. I won’t rehash all of his comments as you can read them at the link below.

However, as he begins his managerial journey, one thing he said did stand out. De Rossi, who always seemed to say the right things when difficult situations arose throughout his career, was very humble when considering the Giallorossi job.

Obviously, I would like to see myself on the Roma bench, but I am in no rush to make it happen tomorrow. If it does happen, it’ll be because I’ve become a good coach rather than having been an important player for Roma.

That says a lot about De Rossi’s character and work ethic. The native Roman doesn’t want to be handed the job based on his on the field merits, but rather for the reputation he hopes to build as a coach. Obviously, De Rossi will have to build his managerial CV from the ground up much like he did as a player. So, now the question is: Where does he begin?

Well, let’s explore a few options that could be on the table for him, as well as, some of the pros and cons of each option.

Option #1: Roma Primavera

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It’s reported that Daniele’s father, Alberto De Rossi, is expected to give up his role as the manager of the Roma Primavera side after 20+ years to potentially take on a coordinator role with Morgan De Sanctis and Bruno Conti. And Corriere dello Sport reported Friday that DDR is a potential candidate to take over for his father.

Pros

The pros with this job are pretty clear for Daniele. First off, he gets to return to the club that he’s spent the majority of his life at, making it a comfortable place to start out his coaching career. He would be entrusted with growing and developing some of the capital’s best talent. Even though he wouldn’t yet be coaching the first team, he’d still be playing a part in its success by building its future as his players graduate to the first team.

By being a part of the organization, it could give De Rossi a leg up when Roma is the market for a new manager down the line. It’s a path that has served Simone Inzaghi quite well at the other end of the Olimpico. His success goes to show that if a manager has the right makeup, he can make the jump straight from the youth set up and have success.

Cons

While Trigoria would provide De Rossi with some familiarity, it could also have some drawbacks. For one, De Rossi would be coaching youth team players, which may not be the best preparation for eventually managing the first team. Additionally, De Rossi wouldn’t be leaving his Roma comfort zone. This could stifle his growth as a manager as he likely wouldn’t face the scrutiny coaching the Primavera side that he eventually would coaching Roma’s first team.

Inazghi’s brother, Filippo, followed a similar path at Milan and things didn’t work out as well for him. The pressure of coaching Roma is similar to that of coaching Milan. De Rossi would have to be ready to succeed right away when he takes over the first team or his legacy could be tarnished similar to Flilippo Inzaghi.

Option #2: The Italian National Team

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It’s long been reported that De Rossi could start his career as an assistant under Roberto Mancini with the Italian national team, but what are the benefits and drawbacks of this high-profile job?

Pros

For one, De Rossi would be learning the ropes from one of Italy’s top managers. Mancini won two Scudetti with Inter and led Man City to an EPL title. Plus, he’s won numerous cup trophies with Fiorentina, Lazio, Inter, City, and Galatasaray. The man knows how to coach. Additionally, De Rossi would get to work with the best players on the peninsula, including some great young talents. Plus, with the Euros being pushed to 2021, De Rossi would be on the bench for a high profile tournament. He could gain invaluable experience working on the sidelines in pressure situations.

Cons

The biggest con to working for the national team would likely be that it’s not a club team. Thus, De Rossi wouldn’t get to experience the day-to-day dealings at club level from a coaching standpoint. The national team doesn’t meet regularly, so De Rossi would gain less immediate experience. Also, by working as an assistant, De Rossi wouldn’t be the guy calling the shots, so he’d likely need another stop as a head coach somewhere to be fully prepared to manage the Giallorossi.

Option #3: Learn From the Best

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Instead of jumping right into a managerial gig, or even an assistant’s job, De Rossi could take a different path. Instead, De Rossi could study under some of the best managers in Europe—something he mentioned in the interview.

Pros

De Rossi mentioned Pep Gardiola by name in the Sky interview and learning from him and other coaches would be a great way for DDR to acquire some of the tools of the trade. He could start with Pep then maybe move on to someone else like Klopp or Conte. De Rossi would be able to learn different tactical approaches to the game, ways to handle training sessions, and even how to manage the various personalities that make up a squad. Consider it a sort of internship.

Cons

The biggest con to this is De Rossi wouldn’t have the responsibilities of a manager or even an assistant. While he would be gaining invaluable knowledge, he wouldn’t be able to put it into practice until he landed a job of his own.

Option #4: Start in the Lower Ranks

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One final option would see De Rossi starting out as a head coach, not with Roma’s Primavera, but rather at a smaller club. Think Serie B. Some other former players like Massimo Oddo, a teammate of De Rossi’s at World Cup 2006, started managerial careers in this way.

Pros

In this approach, De Rossi would still gain head coaching experience without the pressures of starting out a big club. He’d likely be much more able to tinker with tactics and approaches at this level. It would also allow him to manage outside of his comfort zone of Rome.

Cons

The biggest con to all of this is that the coaching experience gained here wouldn’t necessarily be equivalent to managing a big club. He wouldn’t be managing top players or matching wits with top technicians on a weekly basis. This could lead De Rossi to struggle when he does get a crack at Roma or another Serie A side.