Watson: Three critical questions prospective coaches should ask Essendon

Tim Watson has named the three critical questions any prospective coach should ask Essendon prior to accepting the job.

Sat rock bottom of the AFL ladder and without a coach, the Bombers are arguably amid the greatest rut in their long history, with just two wins this season and without a finals win for nearly 22 years.

The appointment of their next head coach is absolutely crucial to the club's future, however, as Watson identifies, understanding why the club has found itself in this position is just as important to any prospective senior coach considering the role.

Before taking the job, Watson has outlined three questions that any applicant should float with the club amid their application process, exploring the inner workings behind three list decisions that continue to haunt the club.

“If I was a prospective coach, this is what I’d want to know,” Watson told SEN Breakfast.

“If I’m going to Essendon, I’m sitting down and I’m being interviewed for the coaching position…”

1) Why didn’t you persist with Patrick Voss?

Taken with the 11th pick of the 2021 Rookie Draft, Voss joined the Bombers but was not afforded a chance in the senior setup.

In his debut season with Essendon, Voss featured 11 times in the VFL, averaging 11 disposals and booting 19 goals.

It was his second season that stood out, averaging 13 touches and three tackles and booting 30 goals in 18 games to be crowned Essendon VFL’s best and fairest for 2023.

However, Voss was delisted by the Bombers at the conclusion of the season, failing to crack into the senior setup despite his strong form in the twos.

Going on to join the Dockers as an SSP selection the following season, Voss was credited with seven AFL appearances in 2024 before securing his place in the seniors, playing 20 games in 2025 and earning cult hero status in Fremantle.

The power forward has booted 39 goals in 20 games this season so far, playing a crucial third tall role in Fremantle’s league-best forward 50.

2) Why didn’t you recognise the talent with Massimo D’Ambrosio?

Unlike Voss, mid-season draftee Massimo D’Ambrosio was given a chance in Essendon’s senior setup, playing 16 games across two seasons before leaving for Hawthorn in 2024.

Taken with the third pick in the 2022 mid-season draft, D’Ambrosio played eight games to run out the Bombers’ ‘22 campaign, showing his promise after a 23-disposal, six-mark performance in a win against the Swans in just his third game.

However, his second season with Essendon wasn’t as smooth as the winger would have hoped, playing just eight games before a knee injury cut his season at Round 13.

Despite being keen to sign on with the Bombers at the conclusion of his 18-month contract, the club refused to budge on their proposed one-year extension, and with D’Ambrosio seeking further security, the wingman joined the Hawks on a two-year deal.

In his three seasons with Hawthorn, D’Ambrosio has shone on the wing, playing 71 games and averaging 20 disposals, carrying a deadly left boot and elite run off the wing.

3) Why didn’t you fight harder to try and keep Sam Draper?

The number one pick of the 2017 Rookie Draft, Sam Draper grew into a cult hero at the Dons before eventually leaving to join the Brisbane Lions.

Making his debut in 2020, the project ruckman developed into one of the Bombers’ most talented players, featuring 22 times in 2022 and quickly establishing himself as the club’s number one ruckman.

Unfortunately for Draper, an achilles injury ended his 2025 campaign after just five games, and with his contract set to expire at the end of the season, the South Australian had significant interest from his home state and beyond.

Opting to join the Brisbane Lions, Draper left the Dons as an unrestricted free agent, with the Bombers having to settle for a compensation pick (Pick 20, 2025) in exchange for their star man.

As it stands, four prospects remain in the running for the Bombers' job: Adelaide assistant Murray Davis, Fremantle assistant Jaymie Graham, Sydney assistant Mark McVeigh and Essendon legend James Hird.

“That will tell me a little bit about the people that have been making the decisions there, and I’d want to know the answer to those questions,” Watson concluded.