Walking the Tightrope of When to Sell a Player

Unless you’ve been living under a rock recently, you’re probably aware that Orlando City has been involved in two transfer sagas during the January window. The Lions have been attempting to sign center back David Brekalo from Viking FK, and have faced some resistance in doing so. OCSC was also in a will-he/won’t-he situation with Duncan McGuire, who was seemingly pushing for a move to Europe and ultimately got his wish. All this got me thinking about how it can be difficult to know when the right time is to sell a player, and how complicated transfers can be for all parties involved.

Let’s look at the McGuire situation. While the striker never came out and said he wanted to head across the pond (before the fact), its easy enough to read between the lines and safely assume that the player, his agent, or both parties were heavily pushing for a move. With McGuire and Ramiro Enrique the only two strikers on the roster who had shown they can score in Major League Soccer, and the club offering Duncan a new deal during the off-season, which was never completed, it’s pretty clear that Orlando fully wanted the Creighton product in purple next season.

The team also fended off several offers from Sheffield Wednesday that were either loan deals, or judged to be below the team’s valuation of the player. If OCSC was going to lose him, it at least wanted to get a hefty chunk of change for him, rather than a loan fee, which would be significantly smaller. Things changed when Blackburn Rovers came in and started throwing some higher numbers around, and this is where the situation got tricky.

As mentioned earlier, the Lions likely fully intended on having McGuire on the team this year, but when a player wants to move on, you can only stand in their way for so long, or risk the situation getting ugly. You only have to look at the twisting and turning timeline that ended with Cyle Larin in a Besiktas jersey to see how strange and adversarial things can get. You can have situations where players lash out against their team, which is exactly what we saw from Brekalo as he felt Viking was preventing him from joining Orlando.

A player coming out and saying those sorts of things isn’t a good look for a team. Players might be hesitant to sign for a club that has a reputation of standing in the way of guys who want to leave, whether that reputation is earned or not. That’s especially bad for teams in MLS, as — like it or not — the league is very much a selling one. The current method of being successful is finding young players, developing them and selling them on, and filling out your roster with experienced vets and a few high-octane Designated Players. Teams in selling leagues need to cultivate a reputation of being player-friendly and willing to let their stars pursue opportunities when they arise. Despite the Larin fiasco, Orlando is making a habit of honoring the wishes of its players when they want to leave, as we saw in recent years with the departure of Ercan Kara, and Daryl Dike going out on loan before he was ultimately sold to West Bromwich Albion, to name just a few.

It’s a difficult balance to strike, though. First and foremost, the club wants to be competitive and win trophies. The longer it can hang onto its good players, the better chances it has of achieving its goals on the field. At a certain point though, you also want to sell those top performers, and do so at a time when you’ll get the most value possible for them. Ideally, all parties involved are on the same page about when the best time is to move a player on, but there are always other considerations, like wanting to be closer to family, wanting a new challenge as soon as possible, or simply wanting to be in a different environment.

Ultimately, Orlando made the only move it realistically could. The Lions could have played hardball and told McGuire he wasn’t leaving, but then you risk the player holding out, playing poorly due to being upset, or becoming a distraction in the locker room. The result isn’t ideal, but deciding when to let someone move on is a very difficult balancing at, and sometimes you have to simply play the cards you’re dealt.