Wagering on Bill Cosby, Roseanne Barr, Donald Trump in “Death Matchups” proposition bets

Monday, 25 March 2019 13:30 EST

Betting on death matchup propsWhoa, My Bookie is getting dark. After a few years of offering a fairly straightforward slate of game lines, odds, proposition bets and futures, the folks there are finally dipping toes in to the waters of “Specials” betting. – and, as they say, things escalated rather quickly.

NFLbets admits a profound fondness for Specials are those props that usually have nothing to do with sports and are instead focused on celebrities or political elections. Most online sportsbooks will post offerings on now traditional proposition bet specials such as “Who will be the next Pope?” and “Gender of the next baby born in the British royal family.”, and some particularly controversial campaigns has helped build the notoriety and brand name of bookmakers such as Paddy Power.

It is, apparently, in the spirit of the outrageous that My Bookie has posted a series of proposition bets entitled “Death Matchups.” We’re not sure how to further lead into these props without just posting ‘n’ analyzing, so here goes. For all of the following, the proposition bet is entitled “Who Will Die First?” unless otherwise noted.

Betty White (5/13) vs Carol Burnett (2/1)

Now right from the start, isn’t this some bad juju? Likesay, isn’t it the law that Americans must adore Betty White as a national treasure? Besides this, Carol Burnett turns 86 in April 2019 – and she’s still playing comedy clubs. No bet here.

Charlie Sheen (1/2) vs Magic Johnson (8/5)

Los Angeles Lakers fans will likely be driving both sides of this prop, with younger Laker backers who never saw Magic play silently, malevolently cover Johnson here in hopes of dislodging him from the general manager position after one of L.A.’s most nightmarish seasons of basketball ever. The smart money here has got to be on Sheen though – why else that crazy -150 line? – as both TMZ and South Park have revealed that Magic has discovered the cure for HIV.

Regis Philbin (20/21) vs Bob Barker (20/21)

Well, this bookmaker ain’t appealing to Millennials here, that’s for sure. Barker turns 96 in 2019 and hasn’t appeared regularly on TV since 2007; Philbin is 88 in ’19 and last did morning TV in ’11. I guess the sheer numbers say to bet on Bob, but -105 ain’t a great payout.

Rosie O'Donnell (4/6) vs Roseanne Barr (11/10)

Now this one was definitely designed with politics in mind, but we’re really stumped as to why the odds on O’Donnell are so unfavorable; she’s just 57 in 2019 and has had no recent reported health issues. By contrast, have you seen Roseanne since her ejection from her own sitcom? She’s *taken up* smoking cigarettes, has little impetus to keep up her health with her career essentially over and is 9½ years older than Rosie. Call this a medium-term investment and back Roseanne Barr at 11/10.

Prince Phillip (5/7) vs Queen Elizabeth (1/1)

Look, yours truly has been losing bets on the death of queen Elizabeth since the late 1990s. We don’t care if she is 92, we’re not touching this one with a 20-imperial foot pole.

Jay Leno (6/5) vs David Letterman (5/8)

Jay Leno has blissfully been off the air for forever, while Letterman may or may not be on Netflix occasionally. These guys are basically both already in the talk show host’s afterlife anyway, right?

Donald Trump (10/11) vs Vladimir Putin (10/13)

Now these odds make no sense, either. Trump is six years older than his Russian BFF and prefers a diet of fast food. One look at the lean Putin shows that this is not at all the case, and Putin often makes a show of public displays of exercise and sport. Can you imagine Trump publicly participating in any form of exercise? This guy probably thinks a pushup is what must be done to the couch so as to get a better view of Fox News.

On top of this is Russian medical technology. Gods only know what the doctors have over there, but if they kept Leonid Brezhnev and Boris Yeltsin alive into their mid-70s despite basketball-sized livers, the well healthier Putin must be good to go for another, what, 25 years or so? Take Trump at 10/11 odds.

Rae Carruth (3/1) vs Ray Lewis (20/1) vs O.J. Simpson (1/10)

Wait a minute, is My Bookie taking some kind of shot at the American criminal justice system? After all, two of these three former NFL players were found “not guilty” in courts of law…

Will Bill Cosby die in prison?

Eighteen months ago, NFLbets would’ve been all over the NO at 5/2 in this proposition bet, but ol’ Dr. Huxtable (remember, ladies, he’s not a real doctor!) was indeed actually sentenced to a bona fide prison for a term beginning in September 2018 – but we’re not rushing to wager on YES at 2/9, either. After all, said prison term could be as short as three years, with Cosby scot free (until the next trial) in late 2021. Do you have enough confidence in the American incarceration system to believe that Coz will serve his full term in prison? If so, consider the names (and current residential status) involved in the above three-way prop.

Free for all: The sex criminals and deviants

Take a look at this lineup:

Jerry Lee Lewis (6/4)
Bill Cosby (1/1)
Woody Allen (5/2)
Roman Polanski (5/2)
Jerry Sandusky (6/1)
Harvey Weinstein (8/1)
Subway Jared (10/1)

Now that’s an interesting field. The best value bet may be Sandusky at age 75, though his current incarceration in a minimum-security jail rather eliminates the possibility of proper prison justice for this child molester. Speaking of child molestation, Jared Fogle might make a great bet here; he’ll likely spend the rest of his life in prison and has already been assaulted once by a fellow inmate. Unfortunately, Fogle is now in a minimal-security federal prison.

Cosby is the most compelling name on this list, as he’s the only one clearly seeing action. Coz had been equal with pervy film directors Woody Allen and Roman Polanski at 5/2 when My Bookie opened this prop. Some of this might be related to the fact that Polanski (86 years old in August 2019) and Jerry Lee Lewis (84 in September) have been culturally irrelevant for essentially the entire 21st century thus far. And on this entire list, Allen (84 in December) is the only one still actively working.

In the final analysis, NFLbets is going to go with the majority on this one: Take Bill Cosby at 1/1 in this death prop, and you won’t even have to feel bad about winning.