Essendon’s biggest AFL trade regrets

Essendon has won some of the most lopsided trades of all time, but not all of the Bombers’ deals have worked out as planned. Which trades would they like to take back?

Mark Williams goals for Essendon.

Essendon has been on the positive side of the ledger in some of the most lopsided trades ever.

The Bombers will probably never top the deal with Fremantle that landed Matthew Lloyd (via a pre-draft compensation selection) and Scott Lucas (pick 4) in 1994 in return for Tony Delaney, Todd Ridley, Dale Kickett and Russell Williams.

They also made some smart plays in recent seasons, landing Devon Smith, Jake Stringer and Adam Saad plus Dylan Shiel — although the price of that deal is still up for debate. Now the Dons are in a high-stakes standoff with Sydney over Joe Daniher.

But even one of the stronger performing clubs at the trade table has had its share of regrets.

With the benefit of hindsight, here are some deals the Bombers might like to take back if they had their time again.

MARK WILLIAMS FOR PICK 16

“The Rifleman” was one deal that definitely backfired for the Bombers. Williams had kicked 242 goals in eight seasons on Hawthorn’s list including two 60-plus seasons before he was shipped to Windy Hill in 2009 in a complex trade involving four clubs (that also paved the way for Shaun Burgoyne’s move to Hawthorn). Essendon gave up pick 16 which was eventually used on Jasper Pittard. Williams’ career highlight at the Bombers was kicking a goal after the siren to tie a NAB Cup match against St Kilda. He played just four home-and-away games for his new club (for five goals) before retiring at the end of 2011.

Essendon’s NAB Cup hero Mark Williams.

RICHARD COLE FOR PICK 23

A first-round draft pick by Collingwood in 2001 super draft, Cole finished sixth in the Magpies’ best-and-fairest in 2004 — enough to convince Essendon to hand over pick 23 at the end of the next season. He never fired in black and red, playing just seven games before being delisted at the end of 2007.

Richard Cole’s career failed to take off at Essendon.

JOSH JENKINS

There isn’t a rush of clubs trying to get their hands on Jenkins this trade period, but we think Essendon would take him for nothing if they had the chance — which they did eight years ago. Jenkins was a rookie pick by the Bombers in 2010 but was traded to the Crows without playing a game for a gain of 10 picks in the draft order; Essendon gave Jenkins and pick 41 to the Crows in return for pick 31. Neither pick added up to much, with the Bombers selecting Jackson Merrett (56 games) and Adelaide recruiting Mitch Grigg (20 games). Jenkins, meanwhile, booted 296 goals. Could he end up back at Essendon before Wednesday’s trade deadline?

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TED RICHARDS FOR PICKS 19 AND 50

The Bombers selected Richards with pick 27 in the 2000 national draft but he was gone after 33 games in a trade to Sydney. The Bombers recruited two handy players with the draft picks they received in the deal — Courtenay Dempsey (133 games) and Sam Lonergan (79 games) — but the Swans clearly won the exchange with Richards going to play 228 games for the Swans over a decade. His best season came in 2012 when he was named in the All-Australian side and helped Sydney win the premiership.

Ted Richards became a defensive mainstay, and fan favourite, at the Swans.

2002 FIRE SALE

Kevin Sheedy says one of the low points in his decorated coaching career was having to make the phone calls to tell club favourites Blake Caracella, Chris Heffernan and Justin Blumfield they were being traded at the end of 2002. The Bombers were desperate to clear salary cap space and didn’t get much in the deals that sent Caracella to Brisbane, Heffernan to Melbourne and Blumfield to Richmond (a year earlier Damien Hardwick was traded to Port Adelaide). The Bombers’ return at the draft that year included Jason Laycock (58 games), Jason Winderlich (129), Darren Walsh (2) and Tristan Cartledge (9), but there was a big win in the form of father-son pick Jobe Watson.

GAVIN WANGANEEN

No one at Essendon would have wanted to give away a Brownlow Medalist and three-time All-Australian but Wanganeen wanted to return to his first club, Port Adelaide, as its inaugural AFL captain when the Power entered the competition in 1997. He went on to play another 173 games and be part of Port’s first AFL premiership in 2004. The Bombers received picks 2 and 25 in the deal and actually ended up ahead if you just go by games played, with Chris Heffernan (pick 2) playing 170 and Andrew Bomford (pick 25) playing 28.

Originally published as Essendon’s biggest AFL trade regrets