Picking fifth in a draft where you want to land one of three or four marquee forwards is a little bit tricky.
Trading up appears to be out of the question, as everyone ahead of you is asking too much.
That leaves you with what's left over after those ahead of you make their judgements, and in a year like this with the top talent apparent, your first, second or third choice isn't likely to be there.
That's the position the Toronto Maple Leafs find themselves in heading into Friday's first round of the NHL draft, where the three players they would like to get their hands on could easily go 1-2-3 and leave them with a much harder choice at No. 5.
As in: Nail Yakupov, Alex Galchenyuk and Filip Forsberg.
Here's the wrinkle this year, though. Picking ahead of Toronto are three teams that have struggled for years and often picked top forwards in the draft without improving their position in the standings.
Edmonton obviously is the best example with three stars drafted in the first round recently and a glaring need on the blueline.
Columbus and the Islanders, meanwhile, haven't had much yet to show for picking an incredible combined 13 forwards in the top nine picks in the last 10 drafts.
(Even though Rick Nash and John Tavares, and a couple others, panned out.)
So do the Oilers, Blue Jackets and Islanders switch things up, fill a need and pick a defenceman high in a draft considered deep on good blueline prospects?
If two of them do, Leafs GM Brian Burke's decision is easy: He takes the forward left over at No. 5.
At the moment, however, the most likely scenario unfolding on Friday night is Yakupov going No. 1 and some combination of Ryan Murray, Galchenyuk and Forsberg following in the next three picks.
That leaves Burke with a tough call: (a) Pick a blueliner, when his biggest need is a centre, or (b) roll the dice on Quebec Remparts star Mikhail Grigorenko, whose stock is sinking like a stone (perhaps unjustifiably), and hope he becomes your big man down the middle.
After all, there seems little question Grigorenko will be available: After putting up 40 goals and 85 points as a QMJHL rookie, he's fallen to as low as 20th on some lists despite being one of the two or three highest skilled players available.
He could be a steal at No. 5.
He could never play in the NHL at all.
That's what makes picking fifth so difficult for Toronto; you're going to get a player with some warts or some risk after the first few names go.
The question is: How much risk is it worth to pick a player at the right position?
Burke said on Wednesday that this is the first time he's been tempted to draft for need, and it's not hard to see why. There's not a lot of room on the Leafs blueline at the moment, especially if they make a successful push for free agent Justin Schultz, and they need another elite player down the middle to push someone like Tyler Bozak down the lineup.
The good news if they do decide to gamble on Grigorenko is that he'll have a couple excellent role models in current Leafs' Mikhail Grabovski and Nikolai Kulemin, who hardly fit the stereotype of "lazy" Russian that appears to have attached itself to Grigorenko for whatever reason.
In a dream scenario, there could potentially even be a great fit there with all three on a scoring line as soon as next season.
It could also turn out to be a disaster if Grigorenko can't find a spot in the lineup and isn't willing to put in time in the minors when big money is available back home.
But if you're Burke and choices one, two and three are gone, you probably have to bite the bullet, take the potential star and hope for the best here.
At No. 5, betting on talent is the way to go. Then you go to work convincing him to stay.