Hot Streaks and Achievements

  • Sunday NFC Championship 10* Top Play Total-49ers/Rams & 5* ATS Gem-Bengals/Chiefs. NFL 10* Top Plays are a red-hot 8-3 L11 and 10-4 L14.
  • Saturday CBB 10* Top Play-Mississippi State/Texas Tech (6:00 ET/ESPN2). CBB 10* Top Plays 86-61 (59%) L146 and dime players up $19,200!
  • Friday CBB 5* Game of the Night wins on Toledo. Friday NBA goes 2-1 with 5* winners on Atlanta -1.5 and Denver/New Orleans over 218.0.


A highly-sought after handicapper on radio and television, Ross Benjamin’s expert advice is heard nationwide.

Active since:  2003

Location:  Hilton, NY

Ross Benjamin has made his reputation in the sports handicapping industry by being one of the sharpest prognosticators since 2003. Included in professional sports handicapper Ron Raymond’s 2008 published book, “50 Greatest Sports Betting Secrets,” he probably says it best: “One of the most underrated handicappers in our industry and probably one of the sharpest ones I know is Ross Benjamin.” 

One of Ross’ often-used phrases when speaking publicly, “if you want to be a successful sports handicapper then start by thinking like a bookmaker.” Ross is now 63 years old and has been directly involved in many capacities of the sports betting industry for the last 35 years. He currently is a sports betting writer and video analyst for OSGA. Ross also is a regular guest on the "Raymond Report Sports Betting Podcast". However. there is nothing he enjoys more than the challenge of picking winners in the NFL, NBA, MLB, NHL, NCAA Football, and NCAA Basketball.

Sports Handicapping Achievements

Playbook Wise Guy Invitational Contest

  • 4th Place-2015 (50 contestants)-Prize
  • 5th Place-2013 (50 contestants)-Prize
  • 1st Place-2003 (73 contestants)-Prize

Sports Watch

  • #1-2010-2011 NCAA Basketball Regular Season: 116-77 (60.1%)
  • #6-2011 March Madness- 28-21 (57.1%)

Oklahoma Sports Monitor

  • #1-2008 March Madness: 29-17 (63%)
  • #1-2007 NFL Playoffs in Net Profit: 9-2 (81.8%)

Big Guy Sports Monitor

  • #1-NHL 2005-2006 Season

Ross the Writer

Current writer/video analyst for the Offshore Gaming Association
​Former writer/video analyst for Sportsbook Review from 2011 to 2017


Former sports betting analyst on the Bob Mathews Show on WHAM 1180 AM in Rochester, New York every Thursday night during the 2018-2019 and 2019-2020 football seasons.
Weekly guest on the Sam and Brad Show on WAKR 1590 AM in Akron, Ohio during the 2018-2019 and 2019-2020 football seasons.
Frequent guest on the Tony George Show in 2014 and 2015 on Yahoo Sports Radio and the Armed Forces Network.
Host of The Ross Benjamin Show: From 09/12 to 03/13 on Sports Talk Radio 1280 AM WHTK in Rochester, New York (current call letters are Fox Sports AM 1280)                    
Host of Winning Sports Advice in 2012 on Blog Talk Radio.
Host of Ross Benjamin Show on Sports Journey Network from April, 2009 to July, 2010
Host of Phoenix Sports Ticket Radio Show in 2006​

Additional Guest Appearances since 2007

KFNS AM 590 "The Fan"-St. Louis, Missouri
WAXY AM 790 ESPN- Miami, Florida
WHBQ AM 560- Memphis, Tennessee
WHTK AM 1280- Rochester, New York (Friday drive time hour)
WJOX AM 690- Birmingham. Alabama
KTIK AM 1350 ESPN-Boise, Idaho
WJDX AM 620-Jackson, Mississippi
CKST AM 1040-Vancouver, British Columbia (aired during the Jim Rome Show)
KTKR AM 760 "The Ticket"-San Antonio, Texas
KZNS AM 1280 "The Zone" Salt Lake City, Utah  


Locker Room Picks Show (Pilot-2013) hosted by Jennifer X. Williams

Network: CBS Sports