In his journey home following the fall of Troy, the Greek mythological hero Odysseus was faced with an impossible choice at the Strait of Messina. On one side of the tight channel of water between Sicily and the Italian mainland was Scylla, a six-headed monster known for snatching up sailors directly from the hulls of their ship. On the other side was Charybdis, a whirlpool that sucks in and drowns ships of all sizes. Odysseus knew the only way home was to go through, so he had to pick a way. After much consideration, he selected to sail closer to Scylla’s side, and while the ship made it through, the monster gobbled up six members of Odysseus’ crew. No matter which way he picked, it was going to be bad.

The Golden Knights are headed towards their own Strait of Messina with the contract situation of Jimmy Schuldt. The 24-year-old Hobey Baker finalist selected Vegas, among a reported 30 offers, and signed his NHL regulated entry-level contract. He joined the team for a month, played in one game, and then had to watch from the press box as he was ineligible to participate in either the NHL or AHL playoffs. His contract expired following the season now just two days away from the start of Rookie Camp (three from on-ice), Schuldt remains without a second contract.

As Schuldt’s “ship” sails towards City National Arena, there’s Scylla, signing a contract too early and giving up money, on one side and Charybdis, holding out and missing the start of camp, on the other.

Schuldt is in the worst spot a player can be in negotiation-wise under the current CBA. He’s a restricted free agent without arbitration rights, meaning he can only negotiate with the Golden Knights (he’s not even eligible for an offer sheet) and he doesn’t have the ability to allow a 3rd party arbitrator to decide on a contract like other RFAs with more NHL service time. Thus, his only true leverage in negotiation is withholding his services. In other words, holding out of training camp.

That being said, missing camp for Schuldt is not like missing camp for Shea Theodore or William Nylander last year, or Mitch Marner this year. Schuldt hasn’t yet proven himself on the NHL level, and with a roster spot wide open, he needs to be in rookie games, preseason games, and in training camp to win the job.

By NHL rule, Schuldt cannot participate in any official team activities without signing a contract. So even if he wanted to come and prove himself before he signs the deal, the CBA forbids it.

Then there are the Golden Knights, who spent the entire offseason selling off pieces in order to become cap compliant. What they are left with is a roster still fully capable of winning the Stanley Cup, but in need of significant contribution from at least one rookie blueliner. Schuldt currently represents the best option to be that contributor. Scylla, signing Schuldt to an overpaid deal when he has no leverage, is on one side, and Charybdis, watching their best defensive prospect miss camp over less than 1% of the salary cap is on the other.

No matter which way they go, there are potential drawbacks, but one way would continue a disturbing path the Golden Knights have followed this offseason.

If Schuldt were to remain unsigned on Thursday, it would be yet another example of a focus on the long-term financials getting in the way of winning the 2020 Stanley Cup. That’s been the theme of the 2019 offseason. Rather than sticking their feet in the ground and going all-in on winning this year (when they certainly have the roster to do it), the Golden Knights have kicked the can down the road over and over and over again to serve the future (when they don’t know what their roster is going to look like). It happened with Haula, Miller, Carpenter, Bellemare, and especially Gusev. If Jimmy Schuldt misses a second of time in training camp, it might be the worst example yet.

It may seem like a stretch now, considering the Golden Knights remain a legitimate contender to hoist the Cup, but if anything but that happens, this offseason will be second-guessed more than the government’s decision to ban alcohol in 1920. (For those non-history buffs, they unbanned it in 1933. It was called prohibition, and you really should have paid more attention in school.)

It’s truly a lose-lose-lose-lose situation for everyone. No matter which side cracks, or even how hard they crack, someone is going to get burned. Schuldt waits, he might give up his best chance to play in the NHL. The Golden Knights wait, and they might further hinder their chances to develop a promising young player. Schuldt signs and he’s probably leaving at least a bit of money on the table. The Golden Knights sign and they may feel they overpaid a player that had absolutely no leverage in negotiation in order to get him on the ice in time for camp.

Scylla’s on one side, Charybdis is on the other. Someone has to make the decision… soon.