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That familiar feeling is back again after Sunday night’s 1-0 loss to NYCFC. Like beating New England to win the shield only to lose to New England in 2020 in pursuit of the cup, the Philadelphia Union won the battle but lost the war of the 2025 season in a rivalry that continues to deliver drama. There’s been a lot of takes in response to the playoff exit but to say this season was anything but a success would be a denial of what it takes to win a Supporters’ Shield. No, it’s not a balanced schedule and yes MLS Cup is the ultimate prize, but there’s plenty to build on and be proud for a team that felt a bit lost in the wilderness after last season.

In the email today:

1. 🐢 Slow Start Put Union Behind Early in Playoff Exit

By Greg Oldfield

Where do we begin?

The Union crashed out of the MLS playoffs in the Eastern Conference Semifinals Sunday night, falling to New York City FC 1-0 at Subaru Park. This was the second time in five seasons the Union won the Supporters’ Shield and failed to advance to the conference finals.

Was winning the Cup too big of an ask?

Since 2012, only two Shield winners have gone on to win MLS Cup. The last team to accomplish the Shield-Cup double was LAFC in 2022. Prior to that, Toronto won both in 2017. Shield winners have only been successful winning MLS Cup eight times in the league’s history, beginning in the early days of D.C. United, who pulled it off twice in three years from 1997 to 1999. That’s a roughly a 27% chance if my math serves me right.

After playing like one of the best teams in the league for most of the season, it’s hard to say anyone saw this coming. But maybe not.

Entering Sunday night, the Union had last played a game on November 1st when they beat Chicago 3-0 on the road in Game 2 of the First Round. They looked good doing it. Aided by a few early miscues from Chicago keeper Jeffrey Gal, the Union cruised into the Eastern Conference semifinals with ease.

But a lot can happen after 22 days.

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🙋‍♂️ Questions Heading Into Close Season

With the end of every Philadelphia Union season comes questions. Here are seven. Email yours to [email protected].

1. Ernst Tanner. He’s denied the long list of allegations against him and while that’s good enough for some in the fanbase, it’s tinfoil hat thinking that these allegations were made up whole cloth or that him continuing at the club wouldn’t be problematic if even a fraction of the claims (which are difficult to prove or disprove) were non-embellished accounts.

2. Alejandro Bedoya, Mikael Uhre, Ben Bender and George Marks are all out of contract while Chris Donovan has an option but likely won’t return and Nathan Harriel seems a gurantee for option exercising. Filling the open roster spots will be key, particularly with Concacaf Champions Cup back in play in 2026. Striker Ezekiel Alladoh is reportedly on the verge of signing with the team so that would take care of Uhre’s spot while a promotion of Stas Korzeniowski to take Dono’s roster spot would make sense. Indiana Vassilev’s new deal was announced on Tuesday.

3. Andre Blake. Blake is a club legend and one of the best goalkeepers in the history of MLS but is it also time to test the market with him and hand the keys to Andrew Rick? Matt Freese’s ascendency perhaps adds some urgency to that question but while Tanner would absolutely pull that trigger would his interim or future replacement do the same?

4. Kai Wagner. Is he going to Inter Miami? Not likely but it wouldn’t be the close season without rumors of Wagner departing. When the day comes it will be devastating but don’t count on it happening until you see a photo of him grinning holding another team’s jersey.

5. Quinn Sullivan’s Return. Quinn’s absence in the postseason was glaringly obvious and while his younger brother continues to make strides and will likely see his minutes increase next season, his return will be key to them making another postseason run in the back half of next season.

6. Veteran Leadership. With the anticipated departure of Bedoya alone the Union will get younger but it will also create an opening for another veteran or two to solidify the team. There’s plenty of options within MLS to do just that.

7. Jim Curtin. Not a Union question but heading into the second year without Curtin, the beloved former coach will be off the payroll and should be one of the top candidates to take over at Columbus Crew now that Nancy is off to Celtic.

3.💧Water Cooler: Schedule Shift Results

Your thoughts on the MLS Schedule Shift were generally positive, which seems to reflect the overall reaction to the change recently announced.

3. 🏟️ Social Post of the Day: Game Day Memes

4. 🔗 Link Roundup

• No plan B. Quentin Hall reflects on the Union’s playoff exit.

• Owen Boyle catches up with former Union standouts in his latest DOOPing Overseas column.

• Oaklyn United generated plenty of offense but just couldn’t find the goals needed to beat SC Vistula Garfield in their win-and-in U.S. Open Cup qualifier on Sunday.

• West Chester and Jefferson are heading into the second stage of the NCAA Division II Women’s Championship this weekend. They are the only two area college programs still playing after Dickinson was bounced in penalties in the Division III men’s tournament on Sunday.

• Congratulations to our friends at Pittsburgh Soccer Now and the Pittsburgh Riverhounds winning their first USL Championship championship.

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