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Chuck O'Brien's Rating System

I'm going to keep this very simple; I don't want you coming to the site with a slide rule and calculator trying to figure out how to play my picks - I just want you to get down on them ASAP.


My picks will be rated on a 10 dime to 100 dime scale so you can effectively understand my money management system.


The 10-to-100 scale is simply a weighted scale to let you know where a 40 dime release, for example, rates in the big picture. So, for example, an 80 dime play is twice as strong as a 40 dime play. And a 60 dime play is three times stronger than a 20 dime play, etc.


Now how much you personally wager on these selections is a decision you should be making based on how big your bankroll is for a given time period (day, week, month or season). You need to determine what percentage of your bankroll you're willing to risk and then look at how I've rated my pick on the 10 dime to 100 dime scale to realize what portion of that bankroll you should be putting in play.


Please - and this I beg of you guys - please follow my ratings; follow my bankroll strategies. That will be the difference between winning and losing. If you don't use foresight when placing your wagers, you could foolishly put yourself in a deep hole from which their is no escape no matter how much I win for you.


Who Is Chuck O'Brien?

I’m Boston born and bred, a product of a working class Irish family consisting of five sons who lived and breathed sports 24/7, 365 days a year.   

I grew up watching Carlton Fisk, Jim Rice and Freddy Lynn at Fenway and Bird, McHale and DJ at the Garden. But by high school my love of sports turned from collecting football and baseball cards to passing out parlay cards to my friends (and a few teachers).   

I don’t know if many of you can understand this, but growing up where I did and as I did, gambling on sports was a way of life. I can remember when I was six-years-old my Dad and uncles discussing betting NFL games at Christmas dinner. I knew what a pointspread was and what it meant to cover the number long before I got to junior high. And trust me, “Uncle Billy” wasn’t one of my Mom or Dad’s brothers; he was my pop’s bookie for probably 15 years until he passed away.   

I’m not going to lie to you, college wasn’t for me. After high school I went the trade school route and became a licensed HVAC technician. You want to talk about finding gamblers at every turn. My God, all the guys talked about was sports and betting and my opinion was solicited day after day.   

So how did I turn into a professional handicapper? Well, you try to make it on $37,000 a year with a wife, two kids and a mortgage in Boston.

I was betting – and winning – to supplement my income when it dawned on me that I could make money selling my selections to all the guys who had been hitting me up for all these years for free. I started small, charging $25 a week to about 10 guys. Those 10 turned into 150 within two years. And two years after that I was out of the HVAC biz and a full-time handicapper. 

Fast forward to 2007. I had met Al DeMarco while he was appearing weekly as an analyst on SNY Daily News Live in New York. He told me about this website and how he wanted to bring top-notch handicappers at an affordable price to the masses. 

I joined the site in April of 2008.

And then I made a really stupid move.

At the end of January in 2013, I quit

Why? Because I was dumb enough to listen to a couple of guys who promised me the world if I went in with them and started a new handicapping site.


All lies and broken promises. I got conned. Even went a few months with no paychecks. Finally I quit right after the NBA playoffs ended in June of 2015. I was once again selling my picks to individual clients until I reached out to Al again and he offered me another shot, which I truly appreciate. 

Then in August of 2017, my contract expired and I was out on my own again. But starting in April of 2018, I'm back because I've found this is a great site to be releasing my plays on and it's my exclusive internet home once more.

Am I still a huge Red Sox fan? You can bet a Curt Schilling bloody sock I am. But I don’t bet based on my emotions.You must be emotionless when you’re a handicapper; no favoritism allowed.That’s the key to my success; my ability to separate myself as a fan versus a handicapper.   

No ridiculous promises from me; I know as well as you do that no one wins everyday in this business. But you watch this page daily. Watch the winners far outpace the losers. Watch the net profit add up. And watch me make us both money because I’m a player, just like you.

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Help Charity Play of the Week Discount Picks
Time Teams Score Stat Open Westgate 5 Dimes Pinnacle CRIS Carib
Thursday, July 19th
7:05 PM
951 STL
952 CUB
Friday, July 20th - NATIONAL LEAGUE
2:20 PM
901 STL
902 CUB
7:05 PM
903 ATL
904 WAS
7:05 PM
905 SDG
906 PHI
7:10 PM
907 PIT
908 CIN
8:10 PM
909 LOS
910 MIL
9:40 PM
911 COL
912 ARI
Friday, July 20th - AMERICAN LEAGUE
7:05 PM
913 BAL
914 TOR
7:10 PM
915 BOS
916 DET
8:05 PM
917 CLE
918 TEX
8:15 PM
919 MIN
920 KAN
10:05 PM
921 HOU
922 LAA
10:10 PM
923 CWS
924 SEA
Friday, July 20th - INTERLEAGUE
7:05 PM
925 NYM
926 NYY
7:10 PM
927 MIA
928 TAM
9:35 PM
929 SFO
930 OAK
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