With a move that sent Massimo D'Ambrosio to Hawthorn sealed, there are questions raised over the lengths that Hawthorn list boss Mark McKenzie went to bring in the now-former Bomber.

A deal was agreed to late on Wednesday, with the Hawks giving Essendon Pick 61 and a future fourth-round selection (tied to Collingwood) in exchange for the 20-year-old.

There was a surprising twist surrounding D'Ambrosio's desired exit from the Bombers, with the club potentially failing to remember the recruitment rules surrounding rookie-listed players.

Essendon and Hawthorn had reportedly engaged in talks throughout the week surrounding D'Ambrosio, with the Hawks keen on sealing a deal with a low-end draft pick. The Bombers reportedly rejected Hawthorn's offer of Pick 63.

Given that D'Ambrosio was offered a third-year rookie contract, his decision to decline an extension automatically allowed him to become eligible for delisted free agency. Eyebrows were raised over the blunder, which could have potentially allowed a move to Hawthorn with nothing in return.

So why did the Hawks make an early move on the speedy utility instead of waiting till after the trade period?

Massimo D'Ambrosio during the Round 16 match between Essendon and the Sydney Swans at the MCG. (Photo by Robert Cianflone/Getty Images via AFL Photos)

Hawthorn list boss Mark McKenzie answered on AFL Trade Radio as to why they went forward with a trade rather than walking D'Ambrosio to their list for free.

"We always like to get the player in if we can", said McKenzie.

"The pick that we used in the trade this year is actually one that we couldn't use from our list spot perspective.

"With Massimo, If we can get him in we're thinking future fourth which is Collingwood's as well.

"We want to get him in. Win your target and get him in as soon as possible. He's a great kid.

"We had those picks at the end, especially the one that we weren't going to use and I think Essendon used it to get their target so I think everybody's pretty happy."

McKenzie also spoke on keeping a strong enough draft hand for the possibility of drafting Hawthorn father-son prospects Will McCabe and Calsher Dear.

South Australian McCabe is emerging as one of this year's best key-position AFL Draft prospects.

The Central Districts defender is the son of former Hawthorn backman Luke McCabe, who played 138 games for the Hawks across a decade from the mid-1990s to the early 2000s.

"The consideration for us was to keep our draft and increase flexibility," he said.

"That gives us the allowance to move out future picks for next year as well to get some more in, but one of our biggest priorities was to keep that future first and future second.

South Australian draft prospect Will McCabe (Image by Rookie Me Central)

"The increased draft hand from this year provides us with some flexibility for those type of considerations."

Dear, the son of late Hawks great Paul, is also likely to make his way to Waverley as a late draft selection or Rookie Draft acquisition.