MLS Insider: Tom Bogert

Which five MLS clubs are facing the biggest offseason this winter?

New York Red Bulls -- group during anthem -- 2019-04-06 -- RBNY v MIN

We're all in love with the transaction, and even just the thought of the transaction. Silly season is an integral part of the 12-month-a-year cycle of soccer around the globe and it's quite fun, with transfer rumors flying about that range from legit to only-in-FIFA

This offseason, of course, is no different. And while every transfer window is huge for each team, whether the club in question is rebuilding for the future or retooling a championship-caliber core, some offseasons are more pivotal than others. For instance, Columbus Crew SC and LAFC – in different stages of their roster cycles – did key work over the summer. Pending unforeseen circumstances, of course, their winters are a bit more straightforward than, say, a team with 16 players under contract. 

Let's leave out expansion sides Inter Miami and Nashville SC from this discussion, as the spotlight has been trained on their preparations for a while now. Here are the five teams with the biggest offseason ahead of them this winter:

Chicago Fire

Given the Fire have a new ambitious owner, a new (old) stadium, new logo and a vacant coaching bench (from head coach all the way down to assistant equipment manager!), this one is easy. Oh, yeah: They opened all three Designated Player spots this offseason as well as moved on from key non-DPs Dax McCarty and Nico Gaitan. They have 16 players under contract; how many will be in the club's 2020 opening-day starting XI?

The biggest holes on Chicago's roster are in attack, where they have to replace Nemanja Nikolic, Aleksandar Katai and Gaitan. They're reportedly swinging for the fences, interested in a $10-million swoop for Mexico striker Alan Pulido. 

Philadelphia Union

Which five MLS clubs are facing the biggest offseason this winter? -,-McKenzie,-Gaddis.jpg

The Union's Mark McKenzie, Warren Creavalle and Ray Gaddis | USA Today Sports Images

This winter is sneakily a huge one in Philly, despite coming off a club-record 2019 campaign. The Union moved on from Haris Medunjanin, Marco Fabian, Auston Trusty and Fafa Picault thus far, opening cap space and allocation money. All the while, the future of Jamiro Monteiro is still undecided as the club aim to bring him back after a successful loan. 

To replace Medunjanin, Philly are seeking a more mobile defensive midfielder to fit their high-pressing system. Fabian had already lost his place to Homegrown midfielder Brenden Aaronson, while Trusty had fallen out of favor behind Jack Elliott and Mark McKenzie. Picault's trade to FC Dallas opens another place in attack. How will the club utilize their open cap space and roster spots? 

Portland Timbers

A mere seven months ago, the Timbers acquired what appeared to be a final piece. Sure, every season brings roster change, but with Brian Fernandez alongside Diego Valeri and Sebastian Blanco, as well as Diego Chara, Larrys Mabiala and Jeremy Ebobisse in support, the club's core would be set for the foreseeable future, it seemed.

How quickly things change. 

Fernandez is no longer with the team and Valeri playing elsewhere in 2020 looked a real possibility. Reports suggest that the Timbers and their club legend will work things out, but they're right back to the search for one more key piece. Will it be another big-money forward, or have the Rose City club's plans changed? 

Houston Dynamo

In the long-term, new Houston head coach Tab Ramos is expected to transform the club's youth prospects as the accomplished former US U-20 head coach defines a path from the academy to the first team. That takes time, though. In the interim, Ramos and co. have a transformational offseason to deal with.

It's already gotten underway in H-Town as the club made a splash by trading for Darwin Quintero and Victor Cabrera, while trading away Romell Quioto and declining Juan David Cabezas' contract option. There's much more to run through, though, starting with Mauro Manotas and Alberth Elis. Both players are subject of interest abroad, while both players have publicly professed their intent to head to Europe one day.

Is this the offseason that happens? If so, who will replace the pair? Will they be young players again or more experienced veterans? 

New York Red Bulls

With Bradley Wright-Phillips and Luis Robles moving on, following departures of McCarty and Sacha Kljestan in years prior, we're officially into a new era for the New York Red Bulls

Behind Robles and BWP, the club may have a few more key players to replace. The Red Bulls also have two key defenders with eyes wandering elsewhere, as Kemar Lawrence has reportedly put in a trade request and Aaron Long's public transfer saga from the summer hasn't gone away, and they've officially parted ways with Michael Murillo, who was transferred to Belgian club Anderlecht.