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Sportsbook Sponsored Picks - Do they want you to win?

I had been considering writing about people online giving picks when they are sponsored by a sportsbook. Then I saw this post on X by Dave Portnoy, the pizza review guy, Bar Stool creator, etc.:


Let me be clear – I’m not ripping Portnoy or anybody else who has a promotional deal with a sportsbook. I’d take one in a heartbeat. I’m guessing I’d need more than, uhm, 0 followers on Facebook and 6 on X. (C’mon, people!)

Portnoy, a partner of DraftKings, as he describes the relationship, offers parlays that people can bet on through DK. I am not completely sure how it works because I’ve never wagered on any of them. I thought DraftKings players could opt-in to bet on his parlay through what I think is a weekly post. But in checking three or four of these posts, I’m not seeing a link that takes people to a page that lets them bet on the parlay. Maybe the link goes away after the games start or players have to recreate the parlay on their betting ticket – which would seem odd. Regardless, Portnoy is at least giving out a parlay that can be bet on DraftKings.

So, I started wondering . . . does DraftKings want his parlay to win? Portnoy alludes to this question, which he’s presumably been asked or heard from other people, in the video. (I don’t know him and have never even tried to ask him.) “I want to win,” he repeatedly says emphatically in his video posted on Sunday. He also admits he hasn’t won any of these types of parlays yet this season, and, I believe, he lost again Sunday.

The easy answer seems too obvious – DraftKings wants him to lose so that they profit from all the people following his lead and betting the parlay. Even though I’ve become much more skeptical of the world in recent years than I once was, that answer just seems too stupid and obvious. First of all, DK can’t be that desperate. Plus, the site and Portnoy would instantly have zero credibility if he was purposely offering parlays destined to lose. He even claims to have bet $25k on Sunday’s parlay. As I said before about one of his bets, I’d be curled up in a ball crying for a week if I lost that much money.

Sunday’s parlay from Portnoy was a 4-leg bet on 4 different quarterbacks throwing “2+ Passing TDs.” First of all, I don’t know if that means 2 or more or at least 3 – I was once burned on that on ESPN’s “Streak for the Cash.” But either way, that’s really tough to get. The odds of +681 tell you that.

Full disclosure, I bet a parlay given out by a local Philadelphia radio guy, Jon Marks, for the opening Cowboys – Eagles game this season. I believe it was a three-leg same game parlay. Marks says he has a relationship with Bet Parx. I rarely bet SGPs, but I liked it, took a shot (with a different sportsbook), and lost. I have no doubt Marks wanted to win, and I think the same about Portnoy.

Yet, I would be leery of these “sponsored” picks. Portnoy says he bets them, and I have no reason to doubt him. I’ve given out my own parlay picks, which I bet (along with all my picks), and, again, would take a sponsorship any day. But parlays are difficult to win, especially those involving a stat for individual players. And remember, the guys giving sponsored picks are working for the sportsbook – not you.

They are at the very least selling you the idea that multi-legged parlays are just something bettors do on a regular basis. And their payouts a very tempting.

Just think about why they’re so tempting – and whether or not you were even thinking about betting the items in the parlay – before signing on to your sportsbook app.

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