Offseason Guides: San Diego FC and Philly both look to take one more step

We’re into hot stove season. Here’s my contribution:

• MLS Free Agency Tiers: Top players available for 2026
• MLS Cup 2026: Top 5 way-early contenders
• Eastern Conference: 5 teams to watch in the winter transfer market

The West teams I’ll be keeping an eye on will be coming on MLSsoccer tomorrow.

And now, here, we’re winding down our offseason guides series. Got two more today, then two more on Thursday, and then I finally rest. Watch the sun rise on a grateful universe.

In we go:

Philadelphia Union

2025 finish: They won the Shield! By definition that makes this a great season, and as the OG Shield truther, I will certainly not be the one to argue with that. But, well, you might’ve heard I still have my doubts about the game model’s effectiveness in the playoffs, or against elite competition in general.

Biggest question: How big a retool are we talking about here?

Usually if you win the Shield you run it back (or something close, anyway). Whoever’s calling the shots for the Union has decided that is absolutely not going to be the case.

• They’ve reportedly agreed to cashfer leading scorer Tai Baribo to D.C. United for $4 million.
• They’ve reportedly agreed to trade former Defender of the Year Jakob Glesnes to the Galaxy for something around $1 million GAM.
• 20-year-old Ghanaian youth int’l forward Ezekiel Alladoh is reportedly inbound on a $4.5 million transfer as a U-22 signing.
• 22-year-old Colombian center back Geiner Martínez is reportedly on his way from Juventud.
• Veteran DP Mikael Uhre was allowed to head into free agency and reportedly won’t be back.

Those are some pretty heady moves for a team that just collected 66 points, but this is the Union way. They’d rather sell a year too early than a year too late, and given their track-record with regard to player development, I can’t argue too much against that.

So who else could be heading out the door? There has been interest in left back Kai Wagner forever, and Nathan Harriel could end up being shopped if they’re serious about making Frankie Westfield the full-time right back.1 What about Olwethu Makhanya, who was great last year and could end up commanding close to eight figures on the transfer market if the right European team comes calling? No way the Union say no to that.

I think it’s even worth mentioning the legend Andre Blake. He’s still the clear No. 1, but he’s 35 and increasingly injury-prone, and 19-year-old Andrew Rick was extremely impressive filling in for him last year.

I don’t think all or even most of the above is going to happen. Hell, I’m not even sure any of it will.

But this is the Union. So it’s all on the table.

Top winter priority: Upgrade the top-end attacking talent.

As stated above, I still have my doubts about the game model’s effectiveness in the playoffs, or against elite competition in general. Relying upon superior intensity and commitment in order to create chances via disruption of opposing possession sequences – or via simply beating them to second balls – has historically proven to be a lot more effective on a random mid-summer Wednesday than it has in the post-season.2

By definition, teams you’re coming up against in the post-season are better organized and less prone to catastrophic errors than teams you run into week-to-week during the regular-season. They also have plenty of time to zero in and scout your pressing triggers. And as for the intensity gap… I’m not saying it doesn’t exist. I’ll just say that if and when it does, it’s rarely as definitive in November as it’s proved to be from March to October.

Still, though, the game model’s not going to change. They hired Bradley Carnell for a reason, and Bradley Carnell is still the head coach. The Union will press balls-out again in 2026.

And so if something is going to change to put them over the top, it’s going to have to be the top-end talent. Philly ball on a budget, so traditionally that’s been tough. But Alladoh has an intriguing profile and a hefty price tag, and maybe Bruno Damiani is in line for a Gass Theorem breakout?

And then, of course, there’s Cavan Sullivan. So far he’s looked the part of an exceptional youth player progressing at a normal rate – i.e. you can see the talent,3 but you can also see that he’s been off the pace whenever he’s played at the MLS level.

Maybe it takes him til he’s 19 or 20 to make the leap. Maybe he never does with the Union because he’s not a great fit for the game model.

Or maybe it all clicks into place this winter. If so, well, suddenly Philly not just running you over; they’re also gonna slice you apart.

State of the roster: Under construction. The good news is they have plenty of GAM to do whatever they want because they get so much out of their academy and down-roster players – guys who don’t cost them any GAM – and because the “sell too soon rather than too late” ethos means they’re constant refilling their coffers.

That means they can go to the 3 DP/3 U-22 roster model (as they did last year) and still have more GAM than they know what to do with.

• 2026 TAM players: Blake, Iloski, Jean-Jacques, Wagner
• 2026 U-22 players: Alladoh, Makhanya, Q. Sullivan
• 2026 DPs: Damiani

Where the XI stands now: I’m going to presume a level of year-over-year continuity aside from the Uhre, Glesnes and Baribo departures. This could very obviously change a great deal between now and first kick, though.

4-2-2-2

• GK: Blake
• LB: Wagner
• CB: Makhanya
• CB: Martínez(???)
• RB: Westfield
• DM: Lukic
• CM: Jean-Jacques
• LM: Iloski
• RM: Vassilev
• FW: Damiani
• FW: Alladoh

Things to know:

• Getting Milan Iloski on the cheap was a very shrewd move by the Union’s front office, but he’s simply not as good playing a sort of hybrid attacking midfield role in a pressing scheme as he was playing as a 9 in San Diego’s possession-heavy approach.
• They have had incredible good fortune with muscle injuries over the years, with Blake being just about the sole exception. But their schedule’s going to be much more dense in 2026, given it starts with CCC play and they’ll also likely target a long Leagues Cup run.

San Diego FC

2025 finish: Atop the Western Conference on 63 points – the record total for an MLS expansion club – followed by a very credible run to the Western Conference finals.

Biggest question: What’s going on with Chucky?

I’m sorry to start this guide off with something relatively negative, but it’s impossible to whistle past the graveyard here. Chucky Lozano was the team’s marquee signing, and when he was on the field he played like a marquee player. Not out-of-this world good, mind you,4 but very clearly an excellent player who could rip a game open in a moment.

But also, he got benched at halftime of an early October trip to Houston. So… not so good and so committed that he couldn’t grab some pine, right? Message sent, maybe?

Yes and no. It was 1-0 Dynamo at break of that particular game; it finished 4-2 to San Diego as they played their best 45 minutes in ages. They scored four goals in a half when they hadn’t scored more than two goals in a full game for three months.

Reports almost immediately came out that Lozano had not taken the benching particularly well, and had a, uh, pretty pronounced disagreement with head coach Mikey Varas. Turns out it was so pronounced that Chucky didn’t even make the next three matchday rosters, which included the first two games of their playoff journey. There are not a lot of a marquee players who talk themselves into that level of banishment, nor a lot of clubs whose culture is so strong that they’d back the coach in this situation!

Now, Chucky eventually apologized on social media and he did make his way back to the picture. But it wasn’t as a starter – he never cracked the XI again after that trip to Houston. In all he played just 120 minutes over the six subsequent games.

Maybe it’s nothing. Maybe it’s all water under the bridge, and Chucky will be back when preseason starts next month, all smiles and totally bought in.

Maybe not, though. He wants to make the World Cup roster, and to do so he’s got to play. If it’s not going to happen in San Diego…

Top winter priority: Get a match-winning No. 9.

The one time los Niños truly ascended was when Iloski was playing as the No. 9. They were a good team otherwise, and showed as much. Often. I’m not knocking them here.

But during the two months Iloski was in between Lozano and Anders Dreyer they were a stampede. From the time he got on the board for his first goal at the start of May to the time he played his last game for the club two months later they went 8W-2L-1D with a +14 goal differential. Over the rest of the season they were 11W-7L-5D, +9. Losing him cost them the Supporters’ Shield.

Amahl Pellegrino can play there, as can likely new arrival Lewis Morgan, as can Lozano. Holdover Marcus Ingvartsen is natural No. 9, as is young Tomás Ángel. So they have good depth and don’t need to rush into anything.5

But man, imagine this team with a guy who fits perfectly in that spot and can not only finish plays off, but elevate the wingers by dropping in. Or maybe better than “imagine,” how about remember this team with a guy like that in there.

I want to see it again.

State of the roster: Because of the clubwide commitment to identifying and developing young players – which primarily means identifying other teams’ young players and then acquiring them for a song,6 but also means crushing the SuperDraft, and raiding free agency, and just generally leaving no stone un-turned – they are in such great shape.

They have a ton of GAM and a number of open premium roster slots. Heaps spun a masterclass.

• 2026 TAM players: Ingvartsen, McNair, Valakari
• 2026 U-22 players: Ángel, Bruseth, Soma
• 2026 DPs: Dreyer, Lozano

Where the XI stands now: It’s just about full, which is what you’d expect from a team that was so good last year. They have lost a bit of depth in midfield – Luca de la Torre’s purchase option was declined, though he was no longer starting by the end of the year – but that’s really outside the purview of this particular section.

The big issue might become the status of Manu Duah, last year’s No. 1 SuperDraft pick who could become this winter’s record outbound transfer among center backs. He sure as hell looks like an 8-figure player to me.

4-3-3

• GK: dos Santos
• LB: Bombino
• CB: McVey
• CB: Duah
• RB: Verhoeven
• DM: Tverskov
• CM: Godoy
• CM: Valakari
• LW: Dreyer
• FW: Pellegrino
• RW: Lozano

Things to know:

• The concussion CJ dos Santos suffered in the playoffs was terrifying. I’m hoping he’s back in time for preseason, but I haven’t seen any updates so I can’t say for sure.
• Heaps and Varas have worked hard to acquire a ton of guys from the 2023 US U-17 national team, to the point that it honestly wouldn’t shock me at all if San Jose playmaker Cruz Medina or Liverpool reserve team No. 9 Keyrol Figueroa are next on the list. Both would fit a need.
• Between Duah and Ian Pilcher, SDFC crushed it with their SuperDraft picks last year. Considering how much GAM they’re sitting on and the fact that Orlando are a little bit cash-strapped and sitting on four picks in the top 20 of the draft… I’m not predicting a trade, but if I had to predict one, San Diego just buying one of those Orlando picks is what I’d go with.