World Cup Exclusive: Clint Dempsey talks Pulisic, Ronaldo, U.S. Men's National Team

By D.J. Siddiqi

Clint Dempsey knows as well as anyone what it takes to produce on the World Cup stage for Team USA.

The 43-year-old played in three World Cups across 13 years of international competition (2004 through 2017), posting the most appearances (143 caps) while ending his career tied for the most goals (57 with Landon Donovan) in program history.

As this year's Team USA prepares for the 2026 World Cup -- as a host country to boot -- there are increased expectations, especially considering captain Christian Pulisic is leading the way. This appears to be the best squad Team USA has fielded in years -- if not ever -- and advancing to the quarterfinals for the first time since 2002 is not out of the question.

However, Pulisic is entering the World Cup on a little bit of a cold streak. The 27-year-old star had gone 19 consecutive games -- club and international play -- without scoring a goal. Pulisic broke that streak in Team USA's 3-2 win over Senegal in Sunday's friendly.

Team USA is going to need Pulisic to be more productive if they hope to go on their first deep run in years.

"It's not ideal to have one of your best players going through a slump, but he's the type of player that shows you that in any given moment that he can turn it on," Dempsey told Casino.ca in an exclusive interview. "I think towards the last World Cup, when maybe he wasn't in the best form in terms of the minutes he was getting at Chelsea, and still was able to get a goal, and two assists in the 2022 World Cup."

"Maybe it's a situation where he's a man that can step up in big moments and big games, and you've seen that throughout his time when he represents the U.S. team. But yeah, it's not ideal to be going through a bad time as you get towards a once-in-a-life opportunity of having a World Cup on home soil. I think he'll be fine. All he needs is one to go in and to get that weight off of his back, so he can play free again."

Dempsey: Pulisic has plenty of help on Team USA

The AC Milan midfielder has the benefit of playing with a solid supporting cast, including the likes of Weston McKennie and Chris Richards.

"The good news is, there's a lot of great players that can help him out," Dempsey said. "Weston McKennie, in terms of how he's playing in Euro ball again. Chris Richards, how well he's played at Crystal Palace, and being able to win a trophy there. That's good and you got players like Tyler Adams, his leadership, and how well Bournemouth has done this year, fighting for a Champions League spot."

"I'm looking forward to what this team can do. I think there's a lot of quality there, and it's just about when the big stage comes on. There is that June 12 game against Paraguay at SoFi Stadium. Are you going to hit the ground running? I hope they do."

Pulisic has not scored in international or club play since December.

Dempsey -- who knows Pulisic personally -- said his stoic nature will be key as he and Team USA navigates through World Cup play.

"I think that's an impressive thing that any professional player has to have, because if you get too high, then you'll lose that edge of what got you there," Dempsey said. "If you get too low, you lose that confidence to get back right. I think it's important to remember that you don't have those big emotional ups and downs that affect you and cause you to be off-breath longer than you need to be. I think if you keep that mindset of kind of an even keel, that it always keeps you focused and keeps you hungry for more success. It's definitely something that helped me in my career, looking at things from that point of view."

Dempsey: Chris Richards biggest key for USMNT beyond Pulisic

While every casual fan knows who Pulisic is, they may not know the rest of the roster. When asked who is the biggest key player -- not named Pulisic -- in Team USA's success, Dempsey said it's Richards.

"I would say Chris Richards, for sure," Dempsey said. "In the back, the presence that he has, the confidence that he plays with, how he's become one of the first names on the team sheet. The grit that he has, the fight that he has, the fact that he's won a trophy now with Crystal Palace only adds to the winning mentality and the confidence that he brings."

"But I also would say Weston McKennie and (Folarin) Balogun, just for the seasons they've had in Europe. It's just difficult to say one player. But when I think of a team sheet, I think of the first names on it: Chris Richards, Tyler Adams, Weston McKennie, Christian Pulisic, and Balogun, for sure."

When asked what the biggest key will be for how far Team USA will advance, Dempsey said other players will be factors, but it's all about how they play as a team along with the key traits of remaining healthy and confident.

"There's other people that are going to be big factors, but who I like to think of as the spine of a team, Antonee Robinson, I think will be used for them on the left," Dempsey said. "His ability to get up and down the field, not only defend, but getting to the attack, and the quality now that he has in terms of his service and adding assists to his game."

"It'll be interesting to see who's going to play on that right side. Is it going to be Sergino Dest or is it going to be Timothy Weah? Who's going to be other centre-back that's going to be with Chris Richards?"

Dempsey: Strong goalkeeping imperative for U.S.

Dempsey says figuring out the goalkeeper position and getting solid play from that position is a must if the U.S. Men's National Team has hopes of making a World Cup run.

"Who's going to be the goalie for us?" Dempsey said. "Obviously, it's looking like Matt Freese, but it's a position that just hasn't been clear-cut and obvious of who has been dominating that position like what we saw in the past -- with Tony Meola, Brad Friedel, Kasey Keller, and Tim Howard. All it takes is one big tournament to make you a household name."

Dempsey is excited about the potential of Team USA, but wishes the group had more time together to fine-tune its chemistry.

"When you really start to break it down, it is a team that can go and do something great," Dempsey said. "But you need all these players to be healthy and confident and working hard for each other and on the same page. We really haven't gotten too many opportunities and looks to see our best 11 play in a lot of matches. And we cut matches and we got a little bit cheated out of not seeing them have to qualify for a World Cup. I think qualifying for a World Cup really brings a team together and tests your mettle, and puts your back against the wall. I think there's a togetherness that's formed from that experience."

Dempsey: Ronaldo with 'most pressure' of any player in World Cup

While Dempsey is well-known for his ties to U.S. soccer, he also played several years in the Premier League and has his finger on the pulse of the game throughout the world.

Legendary soccer player Cristiano Ronaldo will participate in the World Cup at age 41, hoping to bring home the elusive championship for Portugal.

Portugal is on the short list of favorites, and Dempsey said Ronaldo is going to be intent on capping his storied career with a World Cup.

"The player that has the most pressure on him is Cristiano Ronaldo," Dempsey said. "That's the one thing that's eluded him. He's won everything else."

Dempsey teams with Abbott for Real Madrid experience

Leading into the 2026 World Cup, Dempsey is teaming up with Abbott for the Real Madrid experience for the second consecutive year.

The program offers tryouts for 18-to-19 year olds in six major markets (Miami, Washington DC, Houston, Kansas City, Los Angeles, Chicago) and out of the expected 1000-plus participants, the top 16 players will be selected to travel abroad to train with the Real Madrid academy teams, be evaluated by coaches and scouts and tour Ciudad Real Madrid's state-of-the-art facilities.

"Just the opportunity to have the platform that Abbott and Real Madrid are giving these kids a once-in-a-lifetime chance to be selected and go to another country and play in front of one of the best clubs and best coaches in the world," Dempsey said. "Some of these kids have never been on airplanes and never traveled outside the state, perhaps. For me growing up it would have been one of the once-in-a-life opportunities to do something like that, and to kind of test yourself and put yourself in an uncomfortable situation, see how you adapt."