The Rondo: MLS Playoffs Drama, Upset Watch and Superstar Stakes

Inter Miami, Messi and the Chaos to Come

Inter Miami enter October with the weight of inevitability and fragility in equal measure. You can taste the expectation in Fort Lauderdale — Messi or bust — but the postseason has never been kind to the team everyone assumes has to win.

That’s the magic of this league. The Rondo: Who wins, who’s on upset watch and which superstar has the best MLS postseason prospects — it’s everything that defines MLS distilled into one month of pure chaos.

The Favorites and the Fault Lines

Inter Miami are the obvious headliners. Not because they’re tactically perfect — they very much aren’t — but because Messi exists. And because when Messi is locked in, MLS games stop feeling like MLS games. They feel like a documentary being written in real time. They feel staged, theatrical, inevitable.

Yet every expert — even the ones picking them — admits Miami are leaky. They concede transition chances for fun. If Messi isn’t at nuclear form, Miami can be ordinary very quickly. And the margin for error in knockout football is paper-thin.

Philadelphia Union have a far better structural base. FC Cincinnati might be the most balanced team in the league. Vancouver and Thomas Muller are this year’s “how are they suddenly this good?” disruptor. And LAFC now have Son Heung-Min — a literal Premier League superstar — with Denis Bouanga beside him.

You cannot say that sentence lightly.

So Who Actually Wins This Thing?

Tom Hindle is convinced it’s not Miami. And then picks Miami. That’s the Inter Miami paradox. They are too flawed to trust… unless Messi goes celestial, in which case the sport itself bends.

Alex Labidou goes Spurs rather than Heat — picking FC Cincinnati. It makes sense. Cincy are methodical. Coherent. Unsexy in all the right ways. Evander is a top‑five talent. Kevin Denkey is wildly underrated. Miles Robinson has rediscovered full authority.

Ryan Tolmich — well — he tilts toward destiny. “Fool me once, shame on you. Fool me twice, shame on me.” He’s betting Messi doesn’t let failure happen a third time.

This is MLS. All three answers can be simultaneously correct.

Who’s on Upset Watch?

FC Cincinnati v Columbus Crew

You don’t really get “upsets” in MLS unless a 1-seed collapses instantly. The only thing you can bank on is that something insane will happen.

LAFC are the ones Tom Hindle circled — not because they’re bad, but because Austin are awkward. LAFC with Son will score. But can they grind? Can they suffer? Playoff football is about who can make the game ugly on demand.

Minnesota vs Seattle is the kind of matchup that makes longtime MLS fans grin. Alex Labidou flags the Loons. They’ve looked unstoppable some nights, invisible others. Brian Schmetzer and Jordan Morris do not lose elimination games easily.

And then there’s San Diego — phenomenal expansion year, yes. But Ryan Tolmich suggests reality eventually hits. You don’t roll through playoff star power forever.

Hot Seats and Hot Narratives

Seattle Sounders v Inter Miami CF – Leagues Cup Final

Phil Neville in Portland feels like the pressure point. Portland are annoyingly undefined — good on paper, inconsistent in practice.

Mascherano technically should be sweating — but politically, with Messi next to him, he’s probably protected even if things go sideways. Everyone secretly knows it.

Steve Cherundolo is leaving LAFC, so that chair is effectively vacant.

Messi, Muller or Son — Who Goes Deepest?

Phil Neville Portland Timbers 2025

Gut answer across the board: Messi. The logic? He’s Messi.

Muller might have the best team. There are passages where Vancouver operate with a composure very few MLS teams have — almost Bundesliga rhythm to their spacing and decision-making.

Son might be the most lethal direct weapon in transition — especially with Bouanga drawing gravity.

But Messi is Messi. And he’s chased this thing twice already. There is a coldness to him right now that suggests he will not allow a third miss.

Where Does This Messi Season Rank?

LAFC-vs-Atlanta-United-at-BMO-Stadium

Brilliant by any measure — but weird. He was absent a bunch. Miami weren’t juggernauts. There were weeks where they looked like a normal mid-table MLS side plus an alien cameo.

Top five season ever? Yes. Clear number one? Not unless he lifts the Cup.

He is putting up video game numbers again — 29 goals, 19 assists — but last season’s flash felt even more electric when he did play. This year is more relentless availability.

Win MLS Cup, and the argument melts. It becomes legend.

And Now — the Chaos Stage Begins

Los Angeles Galaxy v Los Angeles FC – Western Conference Semifinals

MLS postseason isn’t about logic. It’s about moments. About late‑night Eastern Time goals in rainstorms. About 30‑year‑old journeyman fullbacks becoming viral heroes. About global legends wandering into a league they thought they knew — and being stunned by its playoff brutality.

Miami might win this clean. Or they might get punched out in a seven‑minute spiral in Seattle or Vancouver or Chester, PA.

That’s the Rondo. That’s the joy.

And that’s why nobody really knows anything — except that we’re about to have a ridiculous time.