Stefanos Tsitsipas shows off his flashy game in the Heat.Rdy Freelift Polo ($85)

It’s no secret that Stefanos Tsitsipas is struggling right now. The world No. 11 has lost three of his last four matches and recently parted ways with his father as his coach. That makes it hard to have much faith in the Greek right now, especially at a tournament in which he has struggled in the past. Tsitsipas has never made it further than the third round at the US Open.

With that in mind, it’s a good idea to play Thanasi Kokkinakis on the game spread in their opening-round match at Flushing Meadows. I also think the Australian is worthy of a little moneyline sprinkle.

Tsitsipas has always had a real weakness on the backhand wing. He hits a one-hander and needs ample time to get himself set for that shot. The US Open’s courts, like those in Cincinnati, will not afford much time to do much but react, and opponents—especially aggressive ones like Kokkinakis—are going to be able to pick on that side of the court. But even beyond that, Tsitsipas’ normally world-class forehand isn’t clicking. He’s generally capable of punishing that shot, but he’s been missing it regularly.

Donald Young traded tennis for pickleball. Then the Open came calling

Donald Young traded tennis for pickleball. Then the Open came calling

And he's into the mixed doubles final.

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When you combine all of that with the fact that Stef isn’t even returning that well, Kokkinakis looks like a live ‘dog.

Kokkinakis has played some great tennis since the start of May; he’s 11-7 over his last 18 matches. Sure, some of those wins came at the Challenger level, but he has also scored wins over players like Alexei Popyrin (who won Montreal), Felix Auger-Aliassime and Gael Monfils (who recently beat Carlos Alacaraz) in that span. Kokkinakis is capable of quickly racking up holds and then utilizing his big strokes to move opponents around along the baseline. All of that should make Tsitsipas uncomfortable.

The only thing I’m really worried about here is that Kokkinakis has had some physical issues this year. He didn’t play in Cincinnati, but that also means he’ll be well-rested. If he’s healthy, he really should be able to keep this match close, and even give himself a chance to win.

The Pick: Kokkinakis +4.5 Games (-120) & Kokkinakis ML (+240)