From Alejandro Bedoya last year to Tranquillo Barnetta the year prior, to Rais Mbolhi and Freddy Adu and Bakary Soumare and others before that, the Union have made some of their splashiest signings over the summer.
But current Union sporting director Earnie Stewart isn't a splashy kind of guy. He's about careful scrutiny, analytics and building a foundation.
And with that in mind, he decided that this summer's MLS secondary transfer window, which ended Wednesday night, was not the time for the club to make a move.
"Sometimes I think people want to go very fast with some things," said Stewart, who's been in charge of personnel moves for the last 18 months. "It's as simple as that. It's up to us to judge if going that fast is good. And I don't believe that right now."
Few would argue against prioritizing long-term growth over short-term sizzle, especially for a franchise that's struggled with consistency and roster turnover since their 2010 expansion season.
The counterpoint, of course, is that acquiring a talented player at this point of the season, especially at a key position like attacking midfield, could provide a jolt of energy or even prove to be the missing piece for a team trying to sneak into one of the final Eastern Conference playoff spots.
But it seems like that kind of difference-maker wasn't on the table when evaluating possible options - at least not for the kind of dollars ownership was willing to shell out.
"We don't want to make a mistake and make a judgment for a significant amount of money where it's not right for the Philadelphia Union," head coach Jim Curtin said. "We've been smart and I think sometimes the best move is not to make a move."
While many of Philly's midseason transfers haven't panned out (the Mbolhi move, for one, may have been the worst in Union history), their last two summer signings yielded well-liked and talented players in Barnetta and Bedoya who certainly raised the bar.
But even in both of those cases, they struggled to adjust to the demands of joining a new team and new league with only a couple of months left in the season. It's particularly hard for European-based players who are currently in their offseason or preseason.
"It's a tough time to hit a home run, to have a [Nicolas] Lodeiro-type situation," said Curtin, referring to Seattle's prized acquisition last year who led them to the 2016 MLS Cup.
"This is not an easy league to play in," Stewart added. "It takes time to adapt to the physicality and travel that there is."
Integrating new players into the club, of course, is much easier in January and February when MLS preseason begins. The Union will also then have much more money and roster space at their disposal when Maurice Edu, who's been injured for the last two years, comes off the books, along with others who haven't been giving Philly the necessary bang for its buck.
But it makes sense why fans may be upset no moves got done this week, especially when nearby rival D.C. United opened up its wallet as it never has before. (The fact that the Union announced the signing of a "Chief Tattoo Officer" on deadline day certainly didn't help with the optics, either.)
For now, though, those fans will just have to try to be as patient as Stewart and hope the exciting changes come in a few months. Perhaps some may also take a little bit of solace in the fact that the Union are optimistic they can still do some damage in 2017 with their current roster - even though they're currently in eighth place in the East, sport a 1-7-3 road record, and have a very difficult remaining schedule.
"The difference between being really good and where people perceive us to be, it's not that big," Stewart said. "It's not as big as people think. Is there a difference between our home games and away games? That's for sure. But you only want to add something you know will help you."
Added Curtin: "We'll have a lot of freedom, a lot of flexibility going into the next year and we still have a group we believe can get into the playoffs this year. That's my main focus right now: getting this group into the playoffs. Because from there, we all know anything can happen."