By Jenny Woo, Destiney Lewis, Payton O'Brien, Anna Lexington, Gambling911.com Reporters

This week, like a tired old mare that has run its course, Bodog.com CEO Calvin Ayre is rumored to have gone way overboard this time.

Known as a cross between Eroll Flynn the Swashbuckling swordsman and Richard Branson, Ayre appeared on a collision course with disaster over these past few days while in beautiful Kentucky.

The Derby had not even taken place yet and Ayre was responsible for various debaucheries too graphic for this family site.  Seems he hosted a stag party for a sports handicapping web site owner by the name of Doc Junior, his site is Docsports.com.  Some of the boys, including Ayre himself reportedly ended up in the stables together. 

Ayre, who has gained 20 pounds since we last saw him in LA, is also on a booze binge.

"He is out of control," commented Doc Junior, who wished to remain anonymous. 

Bodog.com this week announced a partnership deal with Brother Derek, the favorite to win this year's Derby.  Ayre reportedly stepped into the wrong stable, yelled out to the horse "Hey Doris!", presumably meaning to say "Derek", and got kicked in the shins by Sweetnorthernsaint.  Ayre was not wearing a shirt!

Ayre, a self-made billionaire, does not come from the land of "socially appropriate etiquette", thus many can relate to him and as a result his online gambling web site, Bodog.com (See Web Site Here) has flourished. 

Has Calvin Ayre sold his soul to the Devil?

A victim of a night out on the town with Calvin Ayre appears left.  That is young Sean Wells from Covers.com who is usually so innocent....that is until he ends up walking into Calvin's web of debauchery and occasional sin.

The rogue demeanor, however, has helped Ayre to build a whole legion of fans, from grannies to teenage girls. 

Erroll Flynn did it.  Why not Calvin Ayre?

Flynn was married three times, to actress Lili Damita from 1935 until 1942 (one son, Sean Flynn); to Nora Eddington from 1943 until 1948 (two daughters, Deirdre and Rory); and to actress Patrice Wymore from 1950 until his death (one daughter, Arnella Roma).

Ayre has never been married but he is rumored to have had flings with nearly 35,000 girls over his short 44 years in existence.  That's more than Mick Jagger!

After appearing on the cover of Forbes "Billionaire" issue, a female Fox News commentator asked a question many females were no doubt wondering, "Are you dating?" to which Ayre responded "Not in the conventional sense."

We interpreted that to be a politically correct way of saying "I skip the dinner and chitchat and just **** them."

Unlike Flynn, who is rumored to have been bisexual (Truman Capote said he had sexual relationships with him), Ayre has never been with another mare....err we meant male.

Flynn shares coffin space with six bottles of whiskey.  Ayre is rumored to have drunk that many bottles in two days while in Kentucky and the weekend had not yet begun!

We have not even begun to receive photos from the stag party, most of which we worry will need to be censored. 

Calvin Ayre hosted stag party turns into a real night-MAYRE!

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Originally published May 6, 2006 12:18 am EST