Chicago Fire-Portland Timbers Preview (8/16/26)

With Leagues Cup firmly in the rear-view mirror, there’s only one thing left for the Portland Timbers to focus on: Major League Soccer. After putting up a solid effort in the nonsense tournament, it’s time for MLS to resume. The Timbers have enjoyed a 6-game homestand, going 4-1-1 in that span and putting themselves back into the playoff hunt. But now they must travel again, and this weekend’s destination is a place that the Timbers haven’t been since 2018: Chicago.

The Fire Report

While it’s been 8 years since the Portland Timbers visited the Windy City, the last meeting between these two clubs occurred on June 21, 2023. How many of you remember this game? Not that many, I’m assuming, because it was a pretty dull affair. Fabian Herbers gave the visitors the lead in the 8th minute before Franck Boli equalized in the 26th. Kei Kamara won the game in the 83rd minute with a free header. For the first time in their history, the Portland Timbers lost to the Chicago Fire.

The 2023 Timbers didn't make the playoffs, with Kamara's late goals representing the 1 dropped point that Portland needed to secure the final playoff spot. The 2023 Fire finished 13th in the East, but were only 3 points back of 9th-placed Charlotte. Their last playoff appearance was in 2017, carried by the exploits of Nemanja Nikolic (remember him?), Dax McCarty, and Chicago Fire World Cup-winner Bastian Schweinsteiger. For a championship-starved city like Chicago (except for the 1990s, 2005, and 2016) their soccer team couldn't even get into contention for a title. 

Maybe that would change in 2024. Ha! Nope! The Fire finished in the absolute basement of the Eastern Conference, but were 9 points ahead of Spoon-winning San Jose. It was the final fall of a team that, in theory, should be one of the giants of MLS based on market size and available resources. Head coach Frank Klopas was fired, and the Fire decided to look for a proven winner to guide the club back to the promised land: Gregg Berhalter.

That should be a long enough pause so you can get your laughter out of your system. But although I wasn't a full-throated Berhalter believer when he was leading the Stars and Stripes to a Round-of-16 exit in the 2022 World Cup, or a hilarious group-stage exit in the 2024 Copa America, you have to admit that the veteran head coach was a pretty good head coach for the Columbus Crew from 2014-2018. Well, aside from losing to the mighty Timbers in the 2015 MLS Cup final. Chicago's hire of Berhalter signaled that their 7-year playoff drought was completely unacceptable. 

With the unacceptability of mediocrity firmly in the rear-view mirror, Berhalter got to work immediately. Everybody was rooting for the 2025 Chicago Fire. After all, they have no natural enemies aside from the Ohio-based clubs. And they were a team that every MLS fan inherently roots for: awesome offense and terrible defense.

That's what types of teams this league was formed to platform. Top-heavy attack paired with bad defense is the finest vintage of MLS heritage. Every game was guaranteed to have at least 4 goals, but you could never be sure which percentage of those goals were allocated to the Fire. Chicago solidified their postseason credentials with a 5-game unbeaten streak to end the regular season. This stretch included wins against Minnesota, Columbus, and Miami (a 5-3 barnburner with 5 of Chicago's 6 shots on target hitting the back of the net) and back-to-back 2-2 draws against Toronto and New England. That late season run boosted the Fire into 8th place and the chance to host Orlando in the Wild Card Game. 

As the Timbers prepared for RSL in their own Wild Card Game, nerves were high in the pressbox as Chicago-Orlando kicked off. Although the Fire moved back to Soldier Field in 2020, the primary tenant (the NFL's Bears) prohibited the Fire from using the oldest (and smallest) stadium in the NFL for their important playoff game. So the Fire were forced to return to their old stomping grounds in Bridgeview for the biggest game for the club since 2017. 

The Fire dominated the first half but had nothing to show for it. Homegrown midfielder Brian Gutierrez gave Chicago the lead in the 48th minute. Providence Park's pressbox erupted. Star striker Hugo Cuypers added goals 2 and 3 in the 57th and 67th minutes, respectfully. A late Tyrese Spicer goal saved Orlando from humiliation, but the night wasn't about the Purple Lions. For the first time since 2009, the Chicago Fire were victorious in a playoff game. You absolutely love to see it. 

Their playoff journey ended in predictable fashion against the Philadelphia Union in the next round. The magic nearly carried them to a shock victory in Game 1 as former Philly defender Jack Elliott scored a stoppage-time equalizer to force penalty kicks. But Elliott and defender Joel Waterman missed their kicks in the shootout, and the series returned to Chicago (Bridgeview) for a must-win Game 2. Tai Baribo gave the Union a 2-0 lead by the 16th minute, and Andre Blake crucially saved a 32nd-minute Gutierrez penalty kick. Bruno Damiani added Philly's 3rd in the 35th minute, and Chicago's season was over. 

2025 was hugely successful for the Fire. Their playoff drought was over, their playoff win drought was over, and they had two of the best attackers in the league in Cuypers (19g/2a in 36 league games) and the wonderfully-named Philip Zinckernagel (15g/13a in 34 league games). Elliott is still a very good MLS center back, but he needed a difference-making partner. The midfield was the key area that needed improvement, especially due to Rominigue Kouame’s inability to stay healthy. U22 defensive midfielder Dje D'Avilla was expected to be a cornerstone, but he needed more help. The Fire were set at goalkeeper with human meme and USMNT international Chris Brady, except in that Game 2 against Philly when backup Jeffrey Gal stepped in and had the gall to give up 3 goals from 3 shots on target. With clear areas of improvement identified, Chicago got off to a quick start in the offseason.

Let's begin with the departures. Tom Barlow, Kouame, and Chase Gasper were not retained at the end of the season. Gutierrez was sold to Chivas, and ended up making the Mexican World Cup squad. Georgios Koutsias and Justin Reynolds also left on permanent deals. 

The incoming players are the real story. Midfielder Anton Saletros was a major addition from AIK. Attacking midfielder Andre Franco arrived in August on loan, tore his ACL, and was acquired permanently in the offseason. Robin Lod joined the Fire from free agency. South African winger Puso Dithejane arrived from TS Galaxy in his native South Africa. But the headline acquisition of the winter was U22 center back Mbekezeli Mbokazi from South African side Orlando Pirates. Mbokazi is an electric factory, just an incredibly fun player to watch. He went to the World Cup with South Africa and put on a show at the tournament.

The Chicago Fire put on a show before the World Cup break. They entered the season stoppage with an 8-2-4 record; good enough for 26 points and 3rd place in the East. The goals of Cuypers were a huge reason why. The Belgian DP striker netted 13 goals in 12 games. However, the Fire reached their “sliding doors” moment during the World Cup break. Legendary Polish striker Robert Lewandowski was a free agent, and he wanted to come to Chicago. Berhalter’s 4-3-3 only allows for one starting striker, so the head coach spent the last month before the break experimenting with a 2-striker system. The Fire still picked up results, but it wasn’t working as well as the 4-3-3. So when Lewandowski did sign for the Fire on June 29th, the questions between him and Cuypers persisted.

Could a 2-striker system work? The speculation surrounding the fit between Chicago’s two centerpiece players ended when Cuypers requested a transfer. Although Lewandowski is a certified legend, and Chicago’s Polish population is thrilled that their national hero plays in their hometown, the decision to recruit over the active Golden Boot leader was utterly stupid from a footballing perspective. Lewandowski is 37 years old, and he probably has one good full season remaining in his oft-exercised legs. Didn’t matter. Cuypers was sold to Monterrey in late July for about $7.5 million; a loss on the club-record fee they paid Gent to acquire him. Was it worth pissing off their best player for a short-term boost in ticket sales and less production on the pitch? 

Chicago’s (9-2-6, 29 points, 4E/8S) first three league games in the Clausura seem to say that the risk of signing Lewandowski wasn’t worth it. Road losses to Miami and NYCFC with a home win against Charlotte (a very bad road team) were a tough way to resume the season after the high-scoring exploits of the Apertura. In addition, a long-term injury to Mbokazi significantly weakened their backline. Maybe the Fire are just cursed?

Maybe a Leagues Cup run could cure some ills? They won their first two games at Bridgeview against Necaxa and Santos Laguna before inviting Cruz Azul to Seatgeek Stadium on Thursday with a spot in the knockout stages on the line for both. Cruz Azul fans filled the suburban stadium, and didn’t wait long to begin the forbidden chant. However, in a rare moment of justice (since it’s literally impossible to get a match abandoned for the chant) Dithejane scored a game-winner in the 3rd minute of second-half stoppage time and booked Chicago’s advancement as the only MLS team to secure 9 points from the league phase. But what made the moment even sweeter was the late winner also eliminating Cruz Azul from the competition, sending their chanting fans home angry and sad. Would you like one more instance of hilarity? Cruz Azul’s elimination bumped Monterrey up a place, and guaranteed a matchup between Rayados and Chicago in the quarterfinals. Cuypers vs. Lewandowski. Fine, I’ll admit it, sometimes Leagues Cup can be fun.

But that game is in a week and a half. Chicago is still intent on holding onto their top-4 spot in the East, especially with NYCFC and Cincinnati hot on their heels. Is there a chance that they’ll rotate for tomorrow’s home game?

CHI Injury Report & Projected Starting XI

Mbokazi and Franco are still nursing their long-term injuries. I don’t know why Mueller isn’t available. Oregel played 79 minutes against Cruz Azul on Thursday.

This is the same lineup that started against Cruz Azul except for two changes. I think Barroso replaces Jonathan Dean at right back and Lod enters for the questionable Oregel. Chicago has to go to Orlando and New Jersey this week, and this is their only home game. It makes sense that they’d want to start as strong as possible. 

The Timbers Report

Thank God that Leagues Cup is over. Now the Portland Timbers (7-3-8, 24 points, 8W/16S) can refocus on league play and climbing back up the table. However, if they are intent on securing their playoff credentials, they have to be better on the road.

The Road Form

Portland hasn’t played a true road game (no, I’m not counting Seattle, that’s our cavernous and smelly house) since losing 2-0 in Miami on May 17th. That’s almost three whole months without a major road game (yeah, yeah, the World Cup break). Do y’all remember how bad the Timbers have been on the road this year?

I’m excluding the Seattle game for obvious reasons. Let’s take a look at Portland’s travels in 2026. They’re 1-1-6 away from home with a -10 goal differential. Their only victory came from Alex Bonetig’s stoppage-time winner in San Diego, which was easily their best road performance of the year (Lumen is Providence North). But outside of that San Diego game, Portland’s other road games have either followed one of two different themes.

The first is the demoralizing 2-0 loss. After the Miami defeat, I noted that the Timbers are putting together a variety pack of 2-0 losses. Colorado, Minnesota, RSL, and Miami all have different characteristics but the same end result. The other theme is the 3-2 choke. The Timbers tied the game late in Houston and should have benefitted from a war crime of a red card from Nick Markanich, but they blew a chance at their own end and gave up a Hail Mary in response. Vancouver was slightly different, as they were run off the pitch in the second half while trying to protect a 2-1 lead. But after Thomas Muller equalized from the penalty spot after a very unfortunate (but correct) Antony handball, the Timbers were on the counterattack trying to regain the two lost points. However, Alexander Aravena made a bad pass, Sebastian Berhalter drove right back down the field, and got on the end of a cutback cross to win the game for the Whitecaps. The 2-2 draw against Montreal doesn’t fall into either of these categories.

Now that Marti Cifuentes is in the building, the Timbers have an opportunity to relearn how to win games on the road. They cannot be run off the pitch immediately, nor can they drop points at the very end of games. Some sort of improvement has to be shown on this front, especially with a big trip to LAFC looming next weekend. 

PTFC Injury Report & Projected Starting XI

Aravena and Mosquera are going to be on here for a while. Bonetig didn’t dress for either of the final two Leagues Cup games after struggling through a painful shoulder against Puebla. Although the report says “upper body,” a shoulder injury is a safe assumption. Smith likewise didn’t dress for Club America or Tijuana. The severity of his injury is unknown. Ariel Lassiter was seen limping off the pitch after the Tijuana game, but he isn’t listed on the injury report. Neither is Kristoffer Velde, who went to the locker room with a trainer immediately after getting subbed off on Thursday. It appears that Brandon Bye’s complete absence from the matchday squad against Tijuana was a purely rest-related move. James Pantemis has passed concussion protocol and is available for selection.

Velde, Kelsy, Da Costa, Bassett, and Fory did not play the full 90 on Thursday. They should be cleared to start. Miller, Surman, and Caicedo went the distance, and they will probably be in the starting lineup tomorrow. Caicedo’s status is interesting given how well Diego Chara has played since the Clausura began, but I think the club captain gets the start against San Diego on Wednesday. Lassiter played the full game against Tijuana, so I think Antony starts in his place. The Timbers are suddenly very thin at winger, while they’re overflowing with capable midfielders. Usually it’s the other way around. Funny how these things work sometimes.

Tactical Preview

Press?

In the Tijuana game, Cifuentes showed a willingness to press high and often in the first half before slightly tempering the aggression in the second. Is that strategy expected to remain in his first road game?

Two factors have to be considered: the heavy workload and the fact that tomorrow's game is on the road. I think it makes more sense for the Timbers to utilize a mid-block and save their energy for counterpressing. They can force Chicago to try and break them down with the ball (a Mbokazi-less Chicago, mind you) and push themselves to regain their turnovers. I think this idea satisfies both of the extenuating conditions. 

The First Goal

Out of 7 Clausura games (Leagues Cup included), the Portland Timbers have scored the first goal in only 2: Seattle away and Puebla. It is vastly important for the Timbers to score first tomorrow. Otherwise they'll have to try and recover points from a losing position; something that most road MLS teams are unable to do. You could also look at this as “not conceding first.” Just take the viewpoint of whichever one is more motivating.

Matchday Info

Broadcast Bulletin

English: Neil Sika & Kyndra de St. Aubin

Spanish: Francisco Rivera

Home radio broadcast from 105.1 The Fan: unavailable on Apple TV

Broadcast platform: Apple TV

Kickoff time: 3:00 PM PST

Kyndra de St. Aubin isn’t one of the most liked commentators on Apple, but she usually gives good game insights. However, she definitely has a bias towards Minnesota United, so it’s going to be nice to hear her on a game without any Minnesota ties. Wait a minute, you’re telling me Robin Lod plays for the Fire now? Sigh.

Referee Report

Chris Penso’s 2026 stats: 10 games, 23.80 fouls/game, 0.5 penalties/game, 5 yellows/game, 0.1 reds/game

This is the first Timbers game that Penso has officiated since sending Jimer Fory off in Game 1 against San Diego last year. Phil Neville infamously offered his “congratulations” to the experienced referee post-game. I would also like to offer some congratulations to Penso, who will be in charge of Cifuentes’ first MLS game. Welcome to the league, coach.

Series History

Historical record: 5-5-1, +5 goal differential

Road record: 1-3-0, +1 goal differential

Current streak: 1 loss

Current road streak: 4 unbeaten

Portland’s well-documented history of losing during Eastern Conference road trips does not include the Chicago Fire. For whatever reason (mostly Chicago being bad), the Fire have never beaten the Timbers at home. Looks like there’s a streak to keep alive tomorrow.

Table Time

Portland is currently on top of the three Western Conference teams that have 24 points. However, if they win tomorrow, they could potentially climb above Dallas and St. Louis (not RSL because wins are the first tiebreaker). But their situation is also a little sketchy because Seattle is playing Vancouver. Ideally, the Timbers would want the Sounders to eke out a 1-0 or 2-1 win against the Whitecaps to keep the Timbers alive in the Cascadia Cup. Any positive Vancouver result would kill Portland’s chances of getting their hands on the rivalry trophy. But given the looming threat of relocation, I’d be perfectly fine if the Whitecaps kept the trophy for another year.

Minnesota is fading hard, with a 7-game winless streak in MLS play stretching back to an early May victory against Columbus. However, that streak was expanded to 9 games after their first two Leagues Cup games. They beat Atlante on Tuesday, but now they have to travel to RSL.

San Diego plays at LAFC in the first El Plastico of the year tonight. That’s important because Los Plasticos travel to Portland on Wednesday. I’ll be keeping an eye on that game, especially because second-season syndrome has hit San Diego pretty hard.

Final Whistle

This preview is probably going to be more delayed than usual. After all, I'm in Chicago for this game, and I had to do some exploring. That exploration allowed me to witness history.

College football often gets compared to European soccer in terms of the fanaticism, but baseball is also an apt comparison. Not because of the actual sport itself, but the way that it shaped our urban fabric.

Plenty of European soccer stadiums are surrounded by neighborhoods. Tonight, I was at Wrigley Field; the second-oldest MLB stadium in the country. Providence Park might be turning 100 this year, but Wrigley is 11 years older than Portland's soccer cathedral. And the area around Wrigley doesn't betray that a very popular professional sports team, one that has existed for 150 years, calls that neighborhood home. The immediate area surrounding the ballpark has changed immensely over the years, but just a two-block walk away leaves you lost in a row of narrow houses with deep lots. Providence Park isn't surrounded by the same type of neighborhood that Wrigley is, but the development around the stadium has been enhanced by the stadium itself. The same can be said for European soccer stadiums. Generations of fans have gone to places like Craven Cottage (as an example), Providence Park, and Wrigley Field over the past decades. Baseball shaped America like soccer shaped England. Which is why when something historic happens in a baseball game, another level of sports nirvana can be reached.

The Chicago Cubs and the St. Louis Cardinals hate each other. That enmity hasn’t quite caught up on the soccer side yet, mostly because they play in two separate conferences and aren’t guaranteed a match every season. Hopefully the new divisional realignment can solve that. Because tonight, every single fan in the stadium was rooting for one specific outcome: a St. Louis Cardinal to hit a home run.

Plenty of Cardinals fans migrate to Wrigley if one of their ten billion divisional games align on a weekend. When debutant Joshua Baez launched a tape-measure home run to center field in the top of the 1st inning, the spread out squads of red shirts erupted into cheers. It was his first big-league at bat, and he became the 145th player to accomplish this feat. But there was something else that was special about his incredible first swing: the fact that it was the first swing of his MLB career at the first MLB pitch that he saw. He became the 33rd member of that club. Immediately, because regular-season baseball is about accomplishing cool feats, I began rooting for Baez to homer in his second at bat.

He did, sending a fly ball over the left-field wall. Suddenly, the exclusive list of 145 was whittled down to 9. By now, the other fans in the stadium were patiently awaiting Baez’s next trip to the plate. In the top of the 6th inning, after Cubs starter Matthew Boyd began the frame with a walk, Baez sent another fly ball towards the right field wall. In the bottom of the 2nd, Chicago’s Michael Conforto (the former Oregon State Beaver) hit a towering fly ball down the foul line. The stadium held its breath as the ball began to arc downwards, wondering if Conforto got just enough on it to drive home the runners on second and third as well as himself. When the ball landed in the right-field stands, the stadium went crazy. Now Baez’s shot was praying on the Wrigley wind to carry him towards history. It did. The same bleacher creatures who popularized throwing opposing home run balls back onto the field now began to wrestle with a sudden payday. The stadium applauded. I had never seen anything like it. The home set of rival fans was cheering for the opposing player. Two ancient enemies, united over something that was bigger than the vast history of America's pastime.

Could an event like this ever happen in soccer? Two sets of rival fans cheering for the same player after they accomplished something that had never been seen before? Probably not. The stakes aren’t the same for every one of the 162 games a team plays in a full baseball season, but every one of the 34 MLS regular season games is vastly important. However, it got me wondering. When the Timbers inevitably get their first MLS hat-trick, would opposing fans cheer?

Hell. No. No one wants to be seen as the team that allowed the Portland Timbers to break their hat-trick duck. Portland and Seattle fans might see eye-to-eye on some things off the pitch, but it’s war once the whistle blows. Baseball will never be soccer, and soccer will never be baseball. But the notes of an ancient rivalry can still provide hilarious tales. Did anyone sitting in the pressbox write about how incredibly funny it is that the Cardinals’ new sensation has the initials J. Baez? And he hit three home runs in his first three at-bats, something that has never been done before, at WRIGLEY FIELD? A stadium that used to be a home to the most freeswinging baseball player who ever picked up a bat, who shared those exact initials? Is this some kind of cosmic joke?

Maybe it’s just a coincidence. But I felt something in my chest when Baez stepped up to the plate in the top of the 1st. I saw his Triple-A stats, with over 30 home runs and 90 RBI. He was a right-handed batter facing a left-handed pitcher whose fastball barely topped 93 MPH. I thought he was going to homer in that at-bat. I told the gentlemen sitting next to me that he was going to homer. Two of them were experiencing Wrigley for the first time, with the third friend acting as their guide. They weren’t big baseball fans, just some friends on a weekend trip. But they were rooting for those home runs just as hard as I was. When Baez was trotting around the bases after making the most memorable first impression that a batter can make, I whispered to them again: “The record is three. He’s going to get it.”

I’m going to take this opportunity to call my own shot. I have only been in Chicago for 12 hours. It is my hometown. I was born here. I haven’t been back here in 10 years. But the energy of a long-awaited return home has filled me with confidence and assured righteousness. I felt the touch of the rain for the first time in months as I walked to the train after witnessing baseball history. I have to trust my gut. I’m going to harness the ancient power of Lake Michigan, Wrigley Field, Joshua Baez and Soldier Field (only two years older than Providence Park) and try something that has never been tried before. A Portland Timber is going to score a hat-trick tomorrow. I guarantee it.

Normally the hat trick curse only comes into effect when a Timbers player is on a brace. I do not know how familiar Marti Cifuentes is with the time-honored tradition of subbing a Portland player off when he has two goals. It might be a wise move if this exact scenario plays out tomorrow given the heavily congested week ahead. But logic and reason must be ignored. Baseball is the sport of variables. So many things have to happen in a perfect sequence for the right outcome to be delivered. The hat trick is coming tomorrow. You heard it here first. If it doesn’t happen, who cares. It’s time to stop running in fear from the spectre of the unassailable goal. Embrace it. Beg for it. Believe in it.

Getting a win is the primary focus of Cifuentes and the entire team for tomorrow’s game. A good result (combined with how that result is earned) could be enough to change some expectations for this club. This team wants to return to prominence so badly. They want to compete for trophies, and they want to win games of soccer. The Catalonian head coach said as much in his first team meeting: “I came here to fucking win.” 

Let’s go fucking win. The climb continues.