Time to play virtual Director of Football for a moment and assess D.C. United's current playing roster...
Between Hamid and Willis, United are pretty well set between the posts. While Hamid's temperament and occasional rash decisions probably leave him on the outside in any conversation about elite MLS goalkeepers, he's edging into that territory. Besides the raw physical and shot-shopping ability, he's beginning to really command his box; tutelage at the hands of Onstad is clearly paying benefits.
In Willis, United have a capable backup. The concern will be if he's ready to be the #1 should Hamid bolt for more lucrative Euro-pastures. Willis is solid, but isn't the game-changer that Hamid can be. Still, if United can keep hold of Hamid, Willis should be numbered amongst the best of the backups in the league.
Assessment: Solid. No need for help unless Hamid heads abroad.
This is a tough one. While the pairing of McDonald and Jakovic is relatively capable and still not yet in their prime, they look vulnerable when not shielded by two holding mids. On paper, matching the brawn and vocal leadership of McDonald with the quiet class of Jakovic should be a win-win, but they're too often caught out making bad decisions on the ball, losing marks, or being poorly positioned.
Dudar promised much coming into the season, but the commanding aerial presence and generally good distribution were marred by alarmingly regular brain-farts and a series of niggling injuries. Given that United have two quality young prospects returning from loan spells in Shanosky and White and with Russell and Woolard both capable of the odd spell in the middle, is Dudar an unnecessary luxury?
Assessment: Reasonably good. If a can't miss upgrade becomes available, take it, but that should't be a priority.
Three-quarters of the way through the season, I would have pinpointed fullback as a prime target for an upgrade or two. I had come to a grudging acceptance of Woolard as a decent enough left back, but saw little to impress elsewhere. But that was before Najar and Korb turned in some surprisingly good efforts on the defensive flanks and Robbie Russell also had some quality outings (perhaps his poor early season form was due to niggling injuries?).
Still, there's more than a hint of need here. Were Russell's playoff performances as an attacking right back indicative of what he still can bring or is he past his sell-by date? Did Korb turn some career corner and suddenly become a viable MLS fullback or was his brief flourish a flash in the pan? Given United's history with concussions, is counting on having Woolard back a reasonable expectation? Has anybody seen Mike Chabala? And, most importantly, is Andy Najar a right back? While I like him coming from deep positions to terrorize defenses, I wonder if that's the most effective use of his talents. Also, you want to get both DeLeon and Pontius on the field, but both seem most effective coming in from the left flank onto their stronger right feet.
Assessment: The need isn't desperate, but it could become so if Woolard can't go and/or Najar is more needed/effective at right midfield.
Another conundrum wrapped in an enigma made marginally easier to assess with the departure of Boskovic. Does Benny go back to the diamond with De Rosario in midfield, or does he stick with the system that proved so effective down the stretch and rely on two holders? Given how much more solid the defense looked with two holders (and how much more involved the fullbacks were allowed to become offensively -- particularly important if Najar projects as a right back) and my own preference for De Rosario operating as a trequartista between the forward and midfield lines, I'd lean towards the latter option.
If that's the case, there's shopping to be done. Kitchen is only going to get better, but he needs a better partner than Saragosa in the long term, preferably one that carries an attacking threat that doesn't allow opposition midfields to sit deep, clogging the area De Rosario and Pontius and DeLeon want to exploit.
While Kitchen did show up in the attack from time to time in the two-holder system, that's not his strength. Nor is it Saragosa's. With all due respect to Lewis Neal and Stephen King, I don't see them as potential answers either, save in the capacity of providing depth. My preference would be to look for a deep-lying string-puller who can pick passes to our dangerous wide men to initiate attacks or find De Rosario drifting between the lines, but that's a big ask on an MLS budget. More likely would be a box-to-box guy who can cover serious acreage defensively and make late runs into the box to take advantage of crosses or loose balls. Either of these types of players carrying the threat of a cannon-shot from distance would be a bonus.
Assessment: The need is clear. Even if Olsen sees De Rosario still in a midfield role, we'd need another quality option with Boskovic gone.
Assuming Najar won't be starting all season at right-back, we've got good options here. Pontius is amongst the best wide men in the league, and Najar and DeLeon are two of the most exciting wing prospects around. With Pontius, Neal, and DeLeon all strongest on the left flank, it's the right that might need to be addressed. True, it's Najar's natural position and both Pontius and DeLeon can do a job there, but if Najar is playing left back and DeLeon is needed on the left (more on this in the next section), what are your options?
Assessment: Depth on the right flank might need to be addressed, but isn't a massive priority. Re-entry or SuperDraft?
Frankly, not having a reliable danger-man up top is probably the number one factor in why United didn't make it to the MLS Cup final. It's been said elsewhere, but all of United's options are half-solutions. Salihi can finish, but doesn't fit Olsen's system. If United were to become a team that created chances for a forward rather than relying on the forward foraging more for themselves, he might be worth giving a shot (zing!), but I just don't see him being a good fit for the hectic pace and physical nature of this league.
Likewise, Pajoy has some really intriguing qualities (committed defensive effort, good in possession, great movement, reasonably strong) but is (1) not a great finisher and (2) too in love with putzing about with the ball, thus killing attacks and allowing defenses to push up, knowing he won't punish them for doing so. Santos is a decent target man and can blast them from distance, but is terribly streaky and spent long stretches on the treatment table to boot.
Given that De Rosario probably has a stranglehold on one of the forward (or hybrid forward/mid) positions, what would you need in a partner, and can any of those currently on the roster provide such? Salihi and Pajoy both seem better fits for other leagues, ones that play a slower game with more intricate and patient build-up. Santos has proven chemistry with De Rosario, but struggles with injury and form and probably isn't the guy you want to be relying on when the stakes are high.
Of course, De Rosario is (or was) that clutch player. Who knows what type of impact he might have had in the post-season if healthy? But how much does he have left in the tank, and can he be the key cog with a revolving cast of forwards and wingers chipping in enough goals to make a designated goal-getter unnecessary? Perhaps. I also wonder if it might not be worth trying Pontius up top with De Rosario. True, Pontius is better when he has room to gather the ball and run at defenders, but he could do that by pulling wide from a forward position, allowing De Leon of drift inside from the left midfield spot and Najar to overlap wide right. The speed to stretch defenses, creating more room for De Rosario to operate, would be a useful option none of our current crop of forwards provide.
Assessment: Finding a dynamic, reliable finisher up top should be high on the acquisition chart, but it isn't necessarily the end of the world if that doesn't come to pass. Better if it does though.
The immediate response to what United so obviously needed down the stretch is that forward should be priority numero uno. I'd certainly be actively scouting for one, but my first priority would be to find a partner for Kitchen in midfield.
Everything about this team (fragility of defense without two shielding mids, the extra cover allowing attack-minded fullbacks to bomb forward, De Rosario dropping off the forward line, Pontius and DeLeon drifting in from the flanks) points to a two-deep system being the best midfield fit for the current roster. Add in that De Rosario's aging legs would probably be better served by a less physically demanding role than central midfield, and I think the priority should be a central midfielder in one of the two molds I identified above: deep-lying playmaker or box-to-box guy that makes late runs into the box.
After that, obviously I think you look to bolster the forward options and address the depth at either right midfield or fullback depending upon where Najar is projected to play.
At least that's how I'd play the offseason if this were my FM save...