Bet On It: Mobile Sports Gambling 'Madness' Arrives In Massachusetts

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“This will be a major launching point in this industry in this state.”

So How Does This Thing Work?

Where do you start if you want to, say, put a few bucks on the Boston Bruins against the Detroit Red Wings Saturday afternoon at TD Garden, or on the Boston Celtics when they travel to face the Atlanta Hawks later that night?

Each of the mobile/online sportsbooks that the Massachusetts Gaming Commission certified to launch on Friday — Barstool Sportsbook, Bet MGM, Caesars Sportsbook, DraftKings, FanDuel and WynnBet — have some type of “bonus bet” promotion designed to draw you in the door and gain your wagering loyalty.

Each promotion has its own spin, and in none of them can you withdraw the initial “bonus bet” amount, only the amount you win off that bet — if a little bit of luck is on your side.

“The bonus bets are great,” said Joe Murray, 98.5-FM on-air host and 98.5 Over/Under radio show and podcast host, told Patch on Thursday. “That seems to be the play to try to get people in early on. You can win with it. But you can only withdraw the amount you win. So you have to win $400 on your $200 in free bets to get your $200.”

Lifshatz put together a handy Twitter thread aggregating the bonus promotions with some requiring them to be wagered within the first week of the launch, broken up into a set of smaller bets ($25 each), and, in one case, the need to “roll it over” at least five times before any winnings can be collected.

The promotions are essentially a “try it for free” before you start wagering your own hard-earned cash.

“There is a wide variety of options for the consumer to choose from with the six companies that are going to launch their mobile product on Friday,” Lou Monaco of BetMassachusetts.com told Patch. “It is best for one to do their own due diligence on each provider and see what suits them both with the service itself and with their own financial means.”

If, or the sportsbooks hope when, you do decide to wager your own money, then those wagers must be tied to a deposit from a bank account — not a credit card — as a safeguard to try to help ensure residents are only wagering money they actually have to spend.

The sites all have information on those who feel they might have a gambling problem and provide tools where bettors can voluntarily place restrictions on themselves in advance on how much and how often they can bet.

Losers Pay, But Winners Pay The IRS Too

One thing to keep in mind with providing that bank information is that there then becomes a record of your wagers. While a cash bet made, won and redeemed at a casino essentially becomes something between you and your civic conscience, tax forms will be sent to those who withdraw winnings of more than $600 from any specific sportsbook platform over the course of the year — just as they would for any other source of documented income.

One advantage to the state granting so many licenses is that customers will be able to “shop lines” for the best odds. DraftKings is a Boston-based company that will update lines in real-time, while Caesars Sportbook, WynnBet and Bet MGM will set lines more in line with their Las Vegas operations.

“Shopping for the next line is going to be huge,” Murray said. “I would shop the line and try to get the best line.”

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Doing that, however, does require creating accounts, and then making deposits to actually place the wager, on up to six different apps, which may be overwhelming for those who just want to “put a couple of bucks” on the game, mostly to keep things interesting.

“Shop lines, of course, if you have the ability to deposit in every sports book,” Lifshatz said. “The more options the better. Getting the best number for your bet, while not important to all people, will most likely result in a better ROI (return on investment) at the end of the year.”

A Few More Tricks Of The Trade

Lifshatz also recommends not falling for social media promotions from those who claim they are “guaranteed winners,” betting consistent amounts, and not “chasing” a bad day with a late bet to “get even.”

“If you have a good day, don’t raise your bet level,” he said. “If you like one game a little more, maybe bet a little more. But consistency is key in keeping your (bet amount) size the same. If you having a good day betting $50 a game, and then all of a sudden you are betting $500 on a game, that is going to mess you up.

“Chasing is a horrendous strategy,” he added. “If you like a game that’s on late, play it regardless. But if you are only playing it because you are chasing (lost bets) from earlier in the day you are going to lose. Unfortunately, I’ve found that the lesson of chasing is something most people can only learn the hard way.”

Murray — who goes by the collective moniker of “The Bankroll Boys” with Lifshatz on their show and podcast — said he is a big proponent of the “bankroll” strategy in which you deposit what you consider an amount you are not afraid to lose, and combine that with any promotional bonuses, to create a “bankroll” that allows you to keep playing for days and weeks without having to make further deposits.

“We’ve been preaching that to people for a long time,” Murray said. “Take some disposable income and then try to roll it over. If that’s $100, don’t bet $100 on one game, but bet $25 on four games here and there, and use that for your betting roll as long as you can.”

(Scott Souza is a Patch field editor covering Beverly, Danvers, Marblehead, Peabody, Salem and Swampscott. He can be reached at [email protected]. Twitter: @Scott_Souza.)

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