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Words come easily for Teddy Greenstein. After all, he was a sportswriter with more than 20 years of experience with the . But it’s not just the written word. Gamblers that interact with the long-time Chicago sports scribe are treated to a smooth voice capable of providing facts and figures across radio and television mediums.
Those entwined parts of Greenstein’s skill set are now center stage for PointsNet, which announced a partnership with Front Office Sports to create “Hustle,” a sports betting newsletter that will be published three times weekly starting next Thursday.
Greenstein, whose full title with the Australian-based sportsbook is senior editor and player development manager, has the final editorial say for Hustle. That is a level of accountability that he always wanted.
Hustle will be the national public-facing part of Greenstein’s expanded role. The newsletter is expected to reach approximately one million people via email. But being director of player development could provide additional resonance for him and PointsBet as they look to gain market share in Illinois, the sportsbook’s top-performing state.
Greenstein had long wanted to write about sports wagering while at the . Long before the U.S. Supreme Court struck down PAPSA in May 2018, he was already incorporating point spreads into his weekly column picking Big Ten games. Even before Illinois legalized sports betting in June 2019, Greenstein had a typical Chicago resident’s wariness regarding state government and a new source of tax revenue.
PointsBet came into Greenstein’s orbit late in the summer of 2020 when he received an email with the PR pitch that Devin Hester would be the sportsbook’s brand ambassador for Chicago.
Greenstein enjoys being an ongoing student of sports wagering. He recalled the surprise of PointsBet’s trading desk sticking to its guns with the Tampa Bay Buccaneers for Super Bowl LV. PointsBet did move the line to create a more balanced handle, which contributed to sportsbooks making bank in Illinois, given the lopsided action on the Kansas City Chiefs.
Previously, he has been part of , PointsBet’s wagering-specific telecasts in cities where the sportsbook can leverage its deal with regional NBC Sports networks, including Chicago and Philadelphia.
Greenstein is willing to lean into parlays, which now comprise a sizable portion of operator revenue. PointsBet mirrors that trend to a degree in Illinois, where those bets account for approximately 20% of the handle and more than 40% of revenue. This year's win rate on parlays is 15% compared to 6.8% for all wagers.
He thinks bettors know parlay wagering is not conducive to building a bankroll, but he will not talk them out of making those bets.
Just in time for the football season, this new project stands a solid shot at immediate success.
Now is the time to check out PointsBet for the latest bonus offers for the upcoming football season. There are also DAILY SPECIALS to check every day of the week!