MASSIMO D'Ambrosio spent most of Deadline Day in the air or sitting nervously in airport departure lounges. By the time his trade from Essendon to Hawthorn had finally been lodged last month, the Victorian had travelled to Airlie Beach, flying via the Gold Coast on a stressful day that eventually saw him land at his new home. 

The 20-year-old wasn't the biggest name to move clubs during last month's Continental Tyres AFL Trade Period, but his desire to move from The Hangar to Waverley Park after just 18 months was more captivating than most moves for a variety of reasons. 

Rookies seldom request trades; no player selected in the Mid-Season Rookie Draft has moved AFL clubs since it was reintroduced in 2019; and the abstruse clause that would allow him to move to Hawthorn as a delisted free agent – second-year rookies not accepting another rookie contract can walk to another club as a delisted free agent – if needed became a point of intrigue.

D'Ambrosio requested a trade during Grand Final week after playing eight games for the Bombers in 2023 – the last four as the sub – following eight appearances in his debut season after being selected at pick No.3 in the 2022 Mid-Season Rookie Draft. 

With Essendon putting a freeze on rookie extensions in the middle of winter, Hawthorn sensed an opportunity and engaged in dialogue with D'Ambrosio's new manager, Julian Petracca from Hemisphere Management, who executed a move that was more complex than it looked on paper.  

But before it got done, D'Ambrosio would have to endure a long Deadline Day that ended seconds before the 7.30pm deadline when the Bombers finally agreed to a deal that cost Hawthorn pick No. 61 and a future fourth-round pick. 

"It was actually a crazy day. I knew there was an opportunity for me to go through the free agency slot, but I just wanted to get the trade done so I didn't have to wait the extra two weeks. I knew Hawthorn would take me through free agency if it got to that, but I wanted it done before that," D'Ambrosio told AFL.com.au at Waverley Park this week.  

"On Deadline Day I was on my way to Queensland with my family. We flew to Gold Coast for two hours then two-hour flight to Airlie Beach. I was on the flight and just biting my nails. We left at 8am and got to Airlie Beach by about 3pm. Jules [Petracca] kept me in the loop and I just can't thank him enough. It was seven o'clock and I was really nervous about it thinking, 'when is this trade going to be done?'

"At 7.15pm, Jules called me and said he thought it was going to be done soon. I was just sitting on the couch up there and got a call from Sam Mitchell. He just said: welcome to the club. I was so relieved. I could then enjoy my holiday. I'm really excited about this next chapter."

Hawthorn offered greater security in the form of a two-year deal and a spot on the senior list, while Essendon started with a one-year extension on the rookie list that eventually increased to two years. But by then, it was too late. D'Ambrosio was determined to pursue the opportunity on the other side of town to not only keep his delayed start to life in the AFL alive, but thriving.

D'Ambrosio's story is well known by now. That is the beauty of the Mid-Season Rookie Draft. He won four league best and fairest awards during his underage career at Point Cook in the Western Region Football League. He was overlooked in his draft year after struggling to recover from stress fractures in his back. He started 2022 at the Western Jets and played for Richmond's VFL side before clubs circled. 

Now with 16 AFL games on the board, a change of management and a trade on his CV, D'Ambrosio has lived a full gamut of football experiences in the past 24 months. 

"I'm such a live in the moment guy and just take everything as it comes. I really enjoyed my time at Essendon, I didn't leave a stone unturned, worked my arse off. I was in and out of the side and that's why I needed security. Getting that security was really crucial for me. That was a big reason to move," D'Ambrosio explained. 

"The last 18 months have been really surreal; from not getting drafted in my draft year to having to work really hard the following off-season to coming through Richmond's VFL program. That helped me get drafted in the end. Once I got drafted, I played literally within the first two weeks. I was very fortunate to do that.

"I worked really hard last off-season and didn't miss a session in the pre-season. Brad [Scott] taught me a lot, he is such a knowledgeable coach, but heading into this new chapter I am really ready for the challenge and use everything I've learned across the last 18 months."

D'Ambrosio earned a Rising Star nomination after collecting 23 disposals and five rebound 50s in just his third game last year, before flaunting his quality by amassing 27 touches and 453m gained against St Kilda in round three earlier this year. Opportunities have proven scarce since then for the classy half-back, but the Hawks view him as more than just a rebounding defender.

"That half-back wing role is probably where Sam sees me," he said. "I think one of my strengths is my kicking and my skills, so to be able to utilise that around the field is the goal. Wing or half-back is where he sees me playing in the future. I'm really excited, hopefully I can bring something to the team."

D'Ambrosio started pre-season with Hawthorn's first to fourth-year players on Monday but is on a modified program until the start of December after undergoing knee surgery three months ago to repair the lateral ligament he tore off the bone. 

For now, the Italian is becoming accustomed to his new surroundings at Waverley Park and becoming accustomed to spending plenty of time in the car commuting back and forth from his family home in Point Cook. It takes 50 minutes in the morning, but up to a two hours on the way home. 

D'Ambrosio will consider moving closer to the club in the New Year but prefers to be surrounded by his large, tight-knit family, who are sharing the ride with him. His Nonna and Nonno live closer to the freeway entrance, so he is staying there a few nights a week, much to their delight. 

"My grandparents live halfway from home, so I've been staying there a couple of nights throughout the week, especially on main training days," he said with his trademark grin, "so it has been nice to have pasta and spend time with Nonna and Nonno."

Hawthorn list manager Mark McKenzie and his recruiting team inside Waverley Park have been busy in recent months. The Hawks also landed Collingwood premiership player Jack Ginnivan, Gold Coast key forward Mabior Chol and favourite son Jack Gunston on Deadline Day, but no move was as shrewd as the move for D'Ambrosio. Low budget, big upside.