There are some no-brainers going into this off-season, including signing Alberto Quintero permanently. There are some slightly tricker but still relatively straightforward calls, like cutting Chad Barrett and signing Jordan Stewart to a small one-year deal. But more than any season in recent memory, there are several genuinely difficult roster problems that have no clear answer. As always, feel free to reference my public spreadsheet of San Jose's contract details with the best information I can find.

Here are the five I find most difficult (and most consequential):

Design a more effective system around Chris Wondolowski, and an alternative when he's not on the pitch

The Quakes talisman has earned his legendary status within MLS over a sparkling career, currently sitting at 4th in the all-time goalscorers list. His movement and positioning are non pareil, his finishing lethal, and none of his best traits appear to be fading with the sands of time.

The problem he presents, however, is that he isn't a true number 9: he instead occupies the space beneath another forward that, in most systems, is occupied by a creative number 10, and therefore more or less necessitates a two-striker formation. If a coach opts for a true number 9, Wondo, and a number 10, that leaves plenty of creativity and goalscoring on the pitch, but leaves the midfield incredibly flimsy and makes it hard to possess the ball or push it up from back to front. If you drop the creative midfielder but leave the two strikers up top, you're much more solid in midfield but the movement becomes incredibly predictable and the "empty bucket" rears its ugly head in the attacking third. If you drop the leading striker and leave Wondo up top on his own, you have no release valve for long balls or ability to get in behind the defense.

I think Dawkins-as-a-forward is one excellent solution to this problem that would work within the current flat 4-4-2 paradigm, and we've seen it the last few matches. Dawkins plays really well in that setup, putting up the highest average WhoScored rating of any San Jose player when he plays that role. Wondo also seems to benefit from having a technical player to combine with. The trouble is what the second-best option is. Goitom and Wondo up top in the 4-4-2 also makes sense, since Goitom's ability to combine resolves some of the "empty bucket" problem, but the Quincy/Wondo pairing up top should no longer be a preferred look in that formation, unless Quincy has a stunning renaissance after returning from injury. I'd prefer for Quincy to be a spot starter and bulldog off the bench.

What I would like to see is more of Kinnear biting the bullet of playing Wondo on his own in a single-striker 4-2-3-1 formation. It has been successful in the past, and if the team manages to add some more quality to their midfield, the blow of giving up a target man will be softened. It would cede the middle of the park less than it has in the last year and a half, and put fewer defensive responsibilities on the likes of Simon Dawkins and any other creative players signed. At the very least, it provides a different look for the defense if the primary mode of attack turns fruitless. Kinnear's preferred method of chasing a lead over the time I've covered him appears to be tossing on more strikers, so starting with a one-striker look might make those substitutions more impactful by presenting a greater contrast.

When Wondo leaves the formation, of course, the one-striker look is vastly preferable: it would allow a single target man (Quincy, Goitom, or someone in that mold) to play precisely the role that Kinnear prefers, while utilizing a modern midfield setup and exchanging Wondo for a different focal point (ideally an elite creator in a number 10 role). Which of course leads me to...

Drop Innocent and fill his DP slot with someone who can live up to the tag

Quakes fans do not need me to explain how big a deal it is when you take a giant whiff on the largest investment in the history of the club. They're going to have to take another swing at the fences this offseason to turn their fortunes around, so they need to think carefully about how to get it right. And that doesn't even deal with the possibility that Innocent has a further guaranteed year, which would add the additional burden of finding a way to offload him despite his albatross contract and pitiful production.

For me, the obvious solution to the gaping hole on the roster is to sign a creative attacking midfielder (not a goalscorer) who can play across the attacking band. In fact, Matías Pérez-García was a fairly ideal positional fit from this perspective. But I'm not advocating that the Quakes go out and sign another MPG: I think they can do quite a bit better with the $1M+/year that Innocent's slot currently occupies (and, lest we forget, that was close to MPG's cap hit too when the transfer fee was factored in).

All the best MLS front offices have recognized this particular sort of player as the best possible use of a DP slot: Mauro Diaz and Diego Valeri are perhaps the most sparkling examples of it. It's the rarest talent profile in the broader soccer universe, and the one that can make the single largest impact on the broader quality of play on the team. Technically adept but non-creative players like Wondo, Alberto Quintero, and Simon Dawkins will all look better playing alongside a genuine creator. Most importantly, it allows for some major tactical flexibility: Wondo would be just fine up top on his own if he had a creator underneath. And if he's not in the lineup, the goals wont dry up completely.

It's hard to find a player of this quality and style in general, but particularly hard to find one willing to play in MLS during the productive part of his career. The Seattle Sounders went to immense lengths to snag Nicolas Lodeiro, for example, and only about a half dozen teams in total have found a real star for the role. Therefore, while the goal is obvious and easy to identify, reaching it will be a stiff test of the new-look San Jose front office's transfer acumen.

Decide Tommy Thompson's future (and initiate a broader youth movement)

It's no secret that San Jose has been one of the older teams in MLS in recent seasons. Contrary to some loud voices within the fanbase, however, that's not necessarily a bad thing in a league where salary cap and roster space is paramount and (selling) transfer fees are relatively meaningless: purchasing young players and selling them on later isn't worth much, and every time a contract expires, you get that space back.

So I'm not categorically opposed to an older roster. The best reason to rely on younger players, however, is that they present the possibility of under-paying for production, which is essential in salary cap leagues. Let me explain: if you sign a rookie contract for a small salary, and turn out to be better than expected, you're "under paying" for their contribution to the team (like Fatai Alashe). If you sign a veteran, however, you usually end up paying exactly what their production on the field warrants (like Marvell Wynne). Many of the younger signings won't work out, but they're easy to move on, and you need to end up taking those gambles in order to ever "beat" the cap. The Quakes have done so with Fatai Alashe, and to a degree with David Bingham, but nowhere else in the roster do we find players who are over-performing their salary and are under team control for at least two years. They'll need to add to those two as soon as possible through the draft (where they won't be getting a particularly good pick), the homegrown system (which is a few years away from producing first-team-level talent), and, most importantly, through young signings in Latin America (the way FC Dallas has done with Fabian Castillo and Mauro Diaz).

Tommy Thompson is the trickiest part of this picture. He's yet to break through into a difference-maker, and he'll likely have a hefty salary demand, but he may still hold the promise to develop into a star since he's still just 21 years old. He's gotten a run of games as the Quakes have faded from the playoff picture, but in none of them was his performance any better than "decent." Of course, only I see a tiny fraction of his training, and genuinely respect the coaching staff's assessments more than my own. If they think he's still on track to become a major difference-maker, they should agree in principle to an extension immediately, since he's in the last year of his deal (the timing might be tricky since the extension would not be exempt from the salary cap like his current homegrown deal), and the front office should direct Kinnear to prioritize Thompson's development over, say, his ideal starting XI in March. If they don't think he has it, they should cut bait immediately and get as many assets as they can in return. The worst possible outcome is continuing to invest time in a developmental project that bears no fruit and then losing him for nothing at the end of next year.

The youth movement has another function: if the homegrown pipeline isn't robust, then blue-chip teenagers in the talent-rich Bay Area region will forego the Quakes Academy in favor of Liga MX youth setups and non-affiliated local clubs. Thompson's homegrown deal, signed three years ago now, is the only one in club history, and famously, he spent extremely little time actually developing in the academy as a youngster. My recommendation is to sign Josh Morton to a deal this January if his college season is strong, and Nick Lima too if MLS decides he qualifies for a homegrown deal.

Make some tough choices with respect to the salary situation

Unfortunately, it appears the Quakes are already on the hook for an over-the-cap level of salary unless they make some painful changes. Stalwart defenders Marvell Wynne, Clarence Goodson, and Victor Bernardez constitute one of the best back lines in the league when fit, but their salaries are all well into six figures, they're all in their 30s, and we still have no idea how able Goodson will be to recover from his season-ending back surgery. Goodson and Bernardez do not have guaranteed contracts for next season, and I'm uncertain about Wynne's status.

Casting all three of them into the void for the huge salary savings may be tempting, but getting equal playing value in younger replacements is easier said than done: the FO would be taking a huge risk. Moreover, the three are important leaders on the team who would represent a major loss in experience and savvy. Fail to offload them, however, and the open DP slot becomes the only real method of improving the team besides minimum salary players. Moreover, it merely kicks the can down the road one year in terms of building the back line of the future.

For me, Bernardez is an obvious candidate to retain as long as he agrees to a one year extension at a slightly lower salary than he's currently at. Goodson was the team's best player in 2015, so his determination is entirely medical: if he can physically still play at a high level, you simply have to bring him back, and you'll likely have the negotiating leverage to get a slightly better one-year deal than the one he's currently on. Marvell Wynne has been one of the team's top performers, but he's a poor stylistic fit as both a CB (due to his size) and RB (due to his lack of technical refinement) in Kinnear's system. His age and wage, furthermore, make him a poor strategic fit in a rebuilding project. If his next year is guaranteed, I would trade him to an expansion team for fungible assets (like GAM or draft considerations). If it isn't, I would let him walk, painful though that might be. If either Goodson or Bernardez are off-loaded, they'll need to be replaced with starting-quality players several years their junior.

Why does this salary space matter? In addition to the ability to sign mid-range players that are essential to success in MLS, including the back line of the future, Aníbal Godoy's contract is entering its last year and he may well be the most important building block for the future of the franchise. To sign him to an extension, which the front office absolutely should, you'll either need more salary space or that TAM-level DP slot. Ideally, you'd prefer to leave the latter open, so try to generate the salary space in the process of remaking the back line.

Decide whether to pick up Henok Goitom's option

I really like his stylistic fit, in the sense that he's the only forward the Quakes have had for several years that I think makes sense as a target man with the ability to combine with his teammates and really play the ball with his feet. I think that a full off-season will help him win the confidence of Kinnear and get more match-sharp. He has major advantages in both height and technical ability on Quincy Amarikwa, the only other viable option the team has. And on that very note, Amarikwa's likely long injury layoff makes having a viable target forward on roster even more important.

What's ambiguous, and a difficult decision to make, is whether Goitom's talent level is good enough to be an essential part of the rotation and whether the money makes sense for that given talent level. To add still more confusion, there's a possibility that his cap hit would be lower if he were paid more, thanks to the Targeted Allocation Money rule. I have no idea how large his 2017 option is, but we can analyze the two likely scenarios: one, he's on the lowest level of DP-range salaries and two, he's a well-paid non-DP.

As a TAM player, Goitom would get a check from the Front Office over half of a million dollars per year, which seems to be a brutal overpay for middling production thus far, yet his cap hit would be just $150k. As a non-TAM player, he'll probably make somewhere in the $300k range. That's a bit rich for my blood, but only just a little bit. I'll admit my faith in Goitom is speculative, but his skill set is fairly rare, and he was insanely productive just one year ago in a solid league. If the coaching staff doesn't believe he'll be able to reach those heights again, they'll have to go on the market for a starting-quality target striker, either in the TAM range ($500-800k) or in the Amarikwa range ($250k), and my preference would be for the former.

Let's integrate the Godoy problem to this one. If Goitom's option is more modest than the above scenarios, something in the $200k range, I would advocate for extending Godoy at a TAM-level, around $600k a year. That would give Godoy the $150k "TAM" cap hit, providing a good amount of space under the cap to spend on other parts of the roster.

Regardless of how this sorts out, the Quakes would do well to acquire some young strikers at minimum or near-minimum salaries as developmental projects to see if they can't strike gold on a backup for the 2017 season that may become a contributor in the long run. It'll be necessary from a depth perspective, and striker is a position where, famously, just as many mid-career stars came from total obscurity (like Jamie Vardy, Oribe Peralta, and of course, Chris Wondolowski) as did from teenage pedigree.

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