Ross Benjamin

Featured Pick
MLB #1 Rank/78-48 & +83.64 Units Run
MLB Money Line Wise Guy Winner
- MLB Money Line Premium Picks are on a sizzling hot streak of 22-4 (85%)!
- MLB Premium Picks overall are 78-48 (62%) and +83.64 units since 5/12/2025.
- Ross “The Boss” Benjamin is currently the #1 ranked expert during this 2025 MLB season.
- Ross continues to be the #1 rated expert over the past 30 days.
Hot Streaks
125-83 (60.1%) & +8505 since Sep 9, 2023 in CFB
60-35 (63.2%) & +5594 since Sep 13, 2024 in CFB
94-58 (61.8%) & +9793 since May 13, 2025, in All Sports
78-48 (61.9%) & +8364 since May 12, 2025, in MLB
22-4 (84.6%) & +6329 since Jun 23, 2025 in MLB Money Line Wagers
19-11 (63.3%) and +2526 since Dec 28, 2024, in Football
Last updated Aug 14, 2:10 AM EDT

All Plays
MLB #1 Rank/78-48 & +83.64 Units Run
MLB Money Line Wise Guy Winner
- MLB Money Line Premium Picks are on a sizzling hot streak of 22-4 (85%)!
- MLB Premium Picks overall are 78-48 (62%) and +83.64 units since 5/12/2025.
- Ross “The Boss” Benjamin is currently the #1 ranked expert during this 2025 MLB season.
- Ross continues to be the #1 rated expert over the past 30 days.

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Consultant Bio
Ross Benjamin has made his reputation in the sports handicapping industry by being one of the sharpest prognosticators over the last 21 years. 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 and sharpest sports handicappers I know is Ross Benjamin.
Ross’s sports betting advice is simple yet prophetic. If you want to be a successful sports handicapper, then start by thinking like an oddsmaker.
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