A couple of super hopeful punters will be hoping for the biggest Brownlow medal upset of all time on Monday, with potential massive payouts riding on Des Headland to become the Dockers' first winner of the AFL's highest individual award.
 
While Geelong's Gary Ablett is the hot favourite to take out "Charlie" - after being beaten by teammate Jimmy Bartel last year - Headland is one of the most unlikely candidates to win, particularly as he was injured for much of the year.
 
However, that did not stop two punters placing similar bets of $200 on the former Brisbane premiership player taking out the award - one at odds of $501 - which could mean a payout of $100,200 - and the other at $251, which would glean winnings of $50,200.
 
Sportingbet Australia, who are holding the bets, are hoping for an upset - although not quite that large - as they are set to payout over $250,000 if Ablett wins the medal.
 
No Brownlow medal winner in the past 76 years has missed four or more matches, but punters believe history will be broken - after opening at odds of $13 at the start of the year.
 
"Even the current $2.20 price is popular … and another client had $70000 on him to finish in the top three for the Brownlow at $1.26," said CEO Michael Sullivan.
 
Ablett's biggest threats for the medal are his 2008 All-Australian teammates, Jimmy Bartel and Brent Harvey.
 
"We think Bartel is great value at $4.25 because the 2007 medallist has played in all of Geelong's 21 wins during the regular season and he is a known vote getter," Sullivan said.
 
"Boomer Harvey is also a strong chance at $4.60 and may upset the Geelong duo because he catches the umpires' eyes and plays with very few vote-stealing teammates."
 
Other big bets include $5,000 on Chris Judd at $12 to win, $30,000 on Matthew Richardson at  $1.70 to be Richmond's top vote getter, and one unlucky punter wasting $667 at $151.00 on Paul Hasleby to take out the medal - presumably before he injured his season-ending knee injury in pre-season.
 
2008 BROWNLOW MEDAL - WINNER
 
Sportingbet Australia Odds
 
Gary Ablett [GEEL]                      2.20                       
Jimmy Bartel [GEEL]                  4.25                       
Brent Harvey [KANG]                  4.60                       
 
Nick Riewoldt [STK]                    15.00                     
Adam Cooney [WBD]                 15.00                     
Simon Black [BRIS]                    17.00                     
Chris Judd [CAR]                        17.00                     
Joel Corey [GEEL]                       17.00                     
Joel Selwood [GEEL]                  21.00                     
Matthew Richardson [RICH]      23.00                     
Matthew Pavlich [FRE]                 51.00                     
 
Dean Cox [WCE]                         201.00                  
Rhys Palmer [FRE]                     301.00                  
Matt Priddis [WCE]                      1001.00                                
Paul Medhurst [COLL]                1001.00                                
Aaron Sandilands [FRE]             1501.00