The 'Entourage Era': 3 Signs Pro Pickleball Is Entering Its Next Competitive Phase

Some of the biggest names in the sport are spending 5 figures a month on the team around them: private chefs, nutritionists, massage therapists, strength coaches, and more.

Everybody talks about paddle technology, grit, and backhand rolls — but nobody's talking about what pros are actually doing off court.

As the strength and conditioning coach to players like Anna Bright and Hayden Patriquin, I'm here to tell you they're doing much more than just drilling and playing rec.

I spent years as a strength and conditioning coach with the Minnesota Twins before pickleball pulled me in. The first pro I started training was Catherine Parenteau in 2021. I was full time with her — handling her training, recovery, and nutrition at home, and traveling to every PPA stop with her.

Once I was immersed in the game, the off-court culture reminded me of a rec league.

• Warm-ups were optional
• "Nutrition" was whatever the tournament venue was selling
• Recovery wasn't even a conversation

That era is long over. And most fans haven't noticed yet.

The shift I'm seeing up close

I train pros like Anna Bright, Hayden Patriquin, Tyra Black, and Travis Rettenmaier, and I'll tell you what the top of the game looks like right now:

The players winning consistently aren't just drilling more. They're doing structured strength and agility work. They're tracking their nutrition (or hiring a chef so they don't have to). They're warming up, doing pre-hab, getting stretched, and treating every match like it's Monday Night Football.

Connor Derrickson – aka That Pickleball Trainer – has become the go-to training and nutrition coach among pickleball's top pros. You can find him here.

The entourage era is here

Want to know how serious it's gotten?

Top pros are traveling with multiple people now. They aren't seeing the therapist working the tournament tent, but a therapist on their payroll who knows their body, flies to every stop, and has hands on them before and after every match.

The Airbnb setups tell the story too.

• Portable cold plunges in the garage
• Compression boots running in the living room while film gets reviewed
• Prepped meals waiting in the fridge the night they land
• Quarterly blood work to catch deficiencies before they become injuries

Five years ago, none of this existed in pickleball. It was far more common to get beers after a match rather than a recovery massage.

Why now?

Three reasons, and they all compound.

1. The money got real. When contracts and sponsorships are on the line, a pulled hamstring isn't just annoying, it's a pay cut. Players are investing in their bodies the way they'd invest in any other asset that pays them.
2. The schedule got brutal. Between PPA and MLP, the best players are competing nearly year-round. You cannot survive that calendar on talent. Durability is a major asset. Playing at 100% Wednesday through Sunday, 25 tournaments a year? That's a heavy workload.
3. The margins got thin. Everyone at the top can play. When skill flattens out, the separator moves downstream: Who's fresher in game three? Who's still exploding to the ball on day three of a tournament? Who didn't get hurt in March?

What this means for the rest of us

Here's the part I love.

Pickleball has sold itself as the sport you don't have to be fit for. That pitch built the sport, and I'm grateful for it. But the pros are proving the opposite is true at every level: the healthier body wins more, hurts less, and plays longer.

If you've watched the pro game at all recently, you've seen it. It’s faster, more athletic, more demanding. It's changing before our eyes.

The pros aren't getting serious about their health because someone told them to. They're doing it because they need to stack every odd in their favor to win.

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