Massachusetts law presently bars “pick‑em” contests that award money for predicting the outcome of sports events, so the short answer is no – Underdog Pick Em will not be legal for Massachusetts players in 2026 unless the state legislature expressly revises its gambling statutes. The Commonwealth’s current statutes, recent legislative proposals, and the platform’s own terms all point to a continued prohibition.
Current Massachusetts Gambling Framework
Massachusetts defines illegal gambling in Chapter 271A of the General Laws, which criminalizes “any game of chance … for which a prize is offered” unless specifically authorized. The law treats fantasy‑sport contests that mimic traditional sports betting as illegal gambling. Since Underdog Pick Em operates as a free‑entry contest where participants can win cash by correctly selecting winners, it falls squarely within that prohibition. The state’s most recent gambling expansion—legalizing sports betting in 2022— applies only to licensed sportsbooks, not to pick‑em games that lack a wagering component.
Prospects for Change by 2026
Legislative activity in 2024 and 2025 has focused on broad‑based gambling reform, including proposals to expand online gaming and create a state‑run lottery expansion. While some bills attempt to carve out a “skill‑based” exemption for fantasy contests, none have passed both chambers. Even if a bill were enacted before 2026, the exemption would likely require a clear distinction between pure skill contests and hybrid pick‑em formats that incorporate cash prizes. Until such language is drafted and signed, Underdog Pick Em remains outside the legal perimeter.
Platform Practices and Compliance
Underdog Pick Em’s terms of service state that the service is unavailable to residents of jurisdictions where it is illegal. The platform uses geolocation technology to block users in prohibited states, including Massachusetts. In practice, the company will deny entry to Massachusetts IP addresses, and any attempt to circumvent the block could expose participants to criminal liability under Massachusetts law. The platform’s compliance measures mirror those of other fantasy‑sport operators that have faced state enforcement actions.
FAQ
What specific law makes Underdog Pick Em illegal in Massachusetts?
Chapter 271A of the Massachusetts General Laws, particularly sections dealing with unlawful gambling and games of chance, prohibits contests that award cash prizes based on sports outcomes without a state license.
Can a Massachusetts player join Underdog Pick Em if they use a VPN?
Using a VPN to hide location does not shield a player from criminal liability. Massachusetts law applies to the individual, not the method of access, and violators can face misdemeanor charges.
Are there any exemptions for “skill‑based” contests?
The state has discussed a skill‑based exemption, but no statute currently codifies it. Existing law treats pick‑em contests as predominantly chance‑based, thus illegal.
How does the 2022 sports‑betting law affect pick‑em games?
The 2022 law authorized licensed sportsbooks to accept wagers on sports events. It does not extend to pick‑em contests, which lack a wagering component and are therefore excluded.
What penalties could a player face for participating?
Massachusetts classifies illegal gambling as a misdemeanor punishable by up to one year in jail, a fine of up to $5,000, or both, plus potential civil forfeiture of any winnings.