Jon Rothstein & Rashad Phillips' 2021 March Madness Preview and Betting Advice

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Andrew Wilsher


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Managing Editor of Pickswise. Born and raised in jolly old London, England, with an undying love for the NFL, NBA, soccer and horse racing. A big-time sports bettor who loves futures markets and backing underdogs. Long-suffering New York Jets fan. For Andrew Wilsher media enquiries, please email

The most wonderful time of the year has finally arrived. March Madness is upon us and it’s time to gear up for two-and-a-half weeks of nonstop college hoops action.

We’ve got a whole host of exciting things going on here at Pickswise, including a huge $10,000 NCAA Tournament Capper Contest, featuring 10 of college basketball’s sharpest experts.

Among those experts is renowned insider and analyst Jon Rothstein, as well as former Detroit Mercy player Rashad Phillips, who has one of the most respected minds in the entire sport. Both of those men feature in our Pickswise Masters of the Madness show, where they give their best bets and predictions across all of the action.

Below are Jon and Rashad’s picks to win the NCAA Tournament, along with their reasoning for why they’re siding with that team. But be sure to check out the full hour-long show for more expert insight and analysis at the bottom of this article.

We also have a dedicated March Madness hub as well as picks on the side and total for every single game in the tournament to ensure you’re as informed as possible before making your bets on the tournament.

Jon Rothstein: Illinois Fighting Illini to win the National Championship

Al Pacino once said “here comes the pain” in the movie Carlito’s Way, and pain is coming for Illinois’ opponents.

I don’t want to play spoiler here, but I’m picking the Fighting Illini to win the national championship because of the mental stamina this team has, and for what they displayed in the Big Ten Championship.

All season long we thought this would be a two-horse race, but the Illini have joined the top tier.

I remember the day they played against Wisconsin without Ayo Dosunmu, and I received a text from Brad Underwood that simply said “Curbello time”. Since that moment, Andre Curbello has been a revelation for Illinois.

It’s the 10-year anniversary since UConn won the national championship with Kemba Walker at the helm, and there’s been a lot of talk this season about Dosunmu having similarities to Walker for Illinois. But if you remember back to 2011, Shabazz Napier was also a critical piece next to Walker as a freshman. Curbello is filling that role. Adam Miller is a key piece here as well for Illinois, and the Illini are 10-1 this season when Miller has scored 10 points or more.

Admittedly, the second game they have in the tournament will be a meat-grinder regardless of who they come up against – Georgia Tech or Loyola Chicago. That game should really be held in an octagon instead of on a basketball court when you think about what the style of play will be like! But I’ve still got complete confidence in Illinois going all the way.

Be sure to check out the tournament winner picks for the rest of our Capper Contest participants, including BetsByBob and Jeff Nadu!

Rashad Phillips: Gonzaga Bulldogs to win the National Championship

I’m gonna go with the Zags here. When you look at what Gonzaga brings to the table – they’re great defensively, they don’t make a lot of mistakes, they’re well-coached – and I love the play of Suggs, Corey, and Drew Timme is as productive a player as anyone in the country. But it’s not only that. When you look into the fabric of the NCAA you always have to follow the guard play, and Gonzaga has a lot of guard play and that’s why I’m so confident in their ability.

You’re going to hear the usual “they don’t play anybody” because of their conference but I don’t think the Bulldogs fit in that narrative. They have some quality non-conference wins – they beat Auburn, West Virginia, Virginia, and we all missed that early December matchup they were supposed to have with Baylor. But I tell you this, Gonzaga is one of those teams that want all the smoke. So I’m going with the Bulldogs because I love what they have to offer.

It’s important to note as well that they beat the #2, #3, and #4 in their quarter of the bracket – Iowa, Kansas, and Virginia – by double digits this season. You’ll have a little doubt as a coach because you don’t want your team to be a little lax just because they beat them earlier in the season. What I would do as a coach is reassure my team and say “hey, these guys lost to us and we beat them convincingly, so let’s go out there and do what we did once again”.

The guard play for me is tremendous with what Gonzaga has – Suggs is a top-five pick, Corey Kispert is a lottery pick, and Timme is an NBA player — they have a lot of depth, and I just think it’s such a confidence builder for them to look at that bracket and think “we beat three of these teams already, so let’s continue that.”

Payback is my only concern. I look at Kansas and I think this team hasn’t played well early on, but there’s something inside these teams where they’ll want to play Gonzaga and get revenge, and that really scares me. Kansas doesn’t have the top-tier players it usually has but now I think collectively they can put it together and really give them a scare.

Want more of Jon Rothstein and Rashad Phillips’ March Madness thoughts? Check out our huge NCAA Tournament preview show, which also features Aaron Torres!

Pickswise is the home of March Madness Predictions. Check out all of our March Madness Picks, including daily March Madness Parlays throughout the NCAA Men’s Basketball Tournament.

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