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Posted by on Feb 8, 2015 in Blog, Music and Concert Reviews, Sports Betting | 0 comments

Matt Lessinger’s Annual Grammy Awards Picks for 2015 (Handicapping the Odds)




Matt Lessinger is one of the most trusted gamblers and wagering analysts I know.  He’s solid.  I don’t need an explanation when I’m told Lessinger has taken a position on a game or an event.  I can be confident that the work’s already been done and he’s on the right side.


This doesn’t mean he always wins, of course.  It just means he’s made a solid wager based on getting the very best value most of the time.  Ideally, that’s all you can hope for when you engage in sports wagering or in the case of what I’m about to discuss — wagering on popular events.

Lessinger isn’t a tout.  He doesn’t sell picks.  He’s not even connected in any way to the sports gambling business.  Yet, over the years, Lessinger has appeared in a variety of public and private forums, ranging from sports betting discussion groups to National Public Radio (NPR).  I’ve followed his advice on my own and bet his recommendations for many years — mostly on non-traditional events.  Lessinger handicaps competitions like boxing, MMA/UFC, team season-win totals, propositions, and (most unusual of all) Grammy Awards, Academy Awards, and things like that.  In fact, he’s perhaps the best handicapper I know on these kinds of once-a-year events, one of the reasons he’s appeared as a guest on NPR to analyze the chances of various artists winning awards.

Lessinger is also a well-established poker writer, having written countless columns for many years.  He also authored The Book of Bluffs.  Lessinger is married and lives in the Bay area.  He and his wife had a baby about a year ago, their first.  Congratulations, Matt.

A few days ago, Lessinger shared his thoughts on tonight’s annual Grammy Awards presentation.  I requested permission to share his analysis with the public.  He agreed.

What follows are Matt Lessinger’s thoughts about the four major categories:

Here come the Grammys!

When I saw the nominations this year, this was my first reaction:  “Sam Smith could easily sweep the major categories.”  And when the odds came out, our initial reactions were vindicated, as he is the favorite or co-favorite in every category.  While that sweep may still happen, let’s look at each category independently:



Sam Smith is -600 and he will win.  There is nothing to see here.  If anyone has a chance in hell of scoring the upset, my guess would be Bastille at +1000.  I am wary that the “who the hell is she?!?” win could go to Brandy Clark, a 38-year-old country artist who is also at 10-1, which would be reminiscent of Esperanza Spalding winning at 20-1 in 2011.  But I don’t feel there is value in betting this category.

No bet.



Here you have Sam Smith at EVEN, and I find that to be good value.  I expected the second betting choice to be Taylor Swift, but it turns out the 2nd choice is Sia, with Iggy Azalea as the 3rd choice and Taylor 4th.  Let’s start by dismissing Iggy Azalea.  The fact that she is +400 is what helps make Sam Smith good value, because she has no chance whatsoever.  If Iggy wins this category I will have her face tattooed on my buttocks.  It is hard enough for rap/hip-hop artists to win in open categories.  It is even harder when they are devoid of genuine talent.

Sia is an interesting artist who has had an up-and-down year in the public eye.  First, she was praised for having 11-year-old dancer Maddie Ziegler be the star of her music video for Chandelier, but then she endured some backlash for having Maddie (then 12) star in another video alongside Shia LeBeouf where some of their interactions could be construed as sexual.  I didn’t think it was any big deal, but you never know how the Grammy voters will react.  Either way, I think +300 is a lower price than she deserves to be.  Taylor Swift is +450 and while she is as popular as any pop artist in the world, there doesn’t seem to be much support for her chances at the Grammys this year.

My bet:  Sam Smith “Stay With Me” at even money.



Sam Smith is -120 and I’m not taking that price.  Every nominee is the same as for “Record of the Year” except they (rightfully) took out Iggy Azalea and instead (rightfully) included Hozier’s “Take Me to Church” which is the 2nd choice at +250 and is an extremely intriguing possibility.  I try not to interject my personal judgment of the music, but if I were voting, Hozier would get my vote.  It is one of those throwback songs where the lyrics are deeply meaningful and could be interpreted in different ways, and the song is both haunting and energizing.  In general, the song is about freedom of expressing sexuality, and as such the LGBT community has latched onto the song, which adds a layer of unpredictability as to its chances of winning the Grammy.  I think it stands a chance, but +250 is not a good enough price.  Sia’s “Chandelier” is +400, and obviously, if she wins “Record of the Year” then I will wish I had her at +400 in this category, but it seems much more likely that she’ll win neither category rather than win both.  Taylor Swift and Meghan Trainor are long shots.

No bet.



Gone are the days when you could get +2000 on the longest shots for “Album of the Year” because Grammy voters have gone rogue in this category so often that betting sites have unquestionably gotten burned.  I had Arcade Fire at 8-1 back in 2011, and while that was my crowning achievement of Grammy betting, that was nothing compared to what I could have won some other years.  Last year Daft Punk was the longest shot at 14-1 and they took it home, and you could show me last year’s list of nominees 100 more times and I could never land on Daft Punk.  In 2008 I took a solid stand against the favorites and bet Vince Gill at 18-1, and got submarined by Herbie Hancock at 22-1.  This is just to give you an idea of how bizarre this category has been in certain years.

This year the co-favorites are Sam Smith and Beyonce, both at +150.  Both have reasonable chances, and both are not worth betting at the price.  If I were voting, I would cast my vote for Ed Sheeran who is at +450.  As far as I’m concerned he had the best album of the year, but that’s just my humble opinion.  My vote doesn’t count, and I don’t think +450 is enough of a price.  Pharrell Williams is the longest shot at +1000, and he would be a shocker of Daft Punk proportions.  Could they do that two years in a row?  Maybe, but it’s not worth +1000 to find out.

The final nominee is Beck at +700.  He is by far the oldest of the nominees and has had the longest and most sustained career.  Other nominees, that won based on their career body of work and not the quality of their latest album?  Tony Bennett in 1995, Bob Dylan in 1998, and Steely Dan in 2001 are three that come to mind.  His nomination is also the one that was least expected, which often turns out to be the one that wins, a la Herbie Hancock, Arcade Fire, and Daft Punk.  Every pattern of Grammy voting points towards Beck as the surprise winner and +700 is about as good as we can hope to get.  Chalk this up as my “best bet” and let’s hope for a score!

My bet:  Beck “Morning Phase” at +700


Disclaimer: I have already placed my bets on these categories on Bovada, so my apologies if you don’t see the same odds at which I got them.

Matt L

Note:  Matt Lessinger can be reached at

POSTSCRIPT:  Lessinger’s picks went 2 for 2, NETTING a return of $800 on a risk of $200 (this is why he’s on NPR, folks).




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