Washington Capitals general manager Brian MacLellan is going to have one of the more complex juggling acts in the NHL over the next year.

His team is just one year removed from its first ever Stanley Cup and is still, as currently constructed, a championship contender that should be one of the best teams in the league this season. They still have their core of stars in place, and they have worked to improve the depth around them with the recent additions of Carl Hagelin (before the trade deadline this past season), Richard Panik, and Garnet Hathaway.

For this season, everything is in place right for another run at a championship.

It is what happens after this season when things will get complicated as Nicklas Backstrom and Braden Holtby will be eligible for unrestricted free agency, while Alex Ovechkin will be set to enter the final year of his contract.

Those are three of the most important players in the history of the Capitals franchise and the backbone of the team that finally brought the Stanley Cup to the district.

It is almost kind of hard to believe that Backstrom and Ovechkin are so close to the end of their deals given how long those contracts were. Ovechkin signed a 13-year, $124 million contract that began during the 2008-09 season, while Backstrom signed a 10-year, $67 million contract for the start of the 2010-11 season. Given how much the Capitals have received in return from those two they might be two of the best contracts signed during the salary cap era (honestly, the only other contenders are the Sidney Crosby and Evgeni Malkin duo in Pittsburgh).

Now they are starting to reach their end because father time is a relentless monster that is always chasing after each and everyone of us. Time really does fly.

MacLellan’s challenge will be figuring out how to keep them, and which one to let go if it should come to that.

Let’s start with the obvious one: As long as he wants to play in the NHL it is almost impossible to believe that Ovechkin will ever wear a sweater that is not the Capitals. He is one of the “one team” icons in the sport, and there is no way Ted Leonsis is going to let him chase Wayne Gretzky’s goal record (and perhaps even reach it) with another team. That is just not going to happen. He stays.

But there is nothing the Capitals can do with Ovechkin’s contract until next July. They can, however, sign Backstrom or Holtby at any point starting right now.

This is where the big decision might have to come in, because given the constraints of the salary cap it is hard to see how they can fit all three on the team beyond this season.

The Capitals have a lot of players signed to long-term contracts, and already have 15 players under contract for 2020-21 and 13 players under contract for the 2021-22 season. Trying to figure out what the salary cap is going to look like in either of those years is nearly impossible right now, but the Capitals already have $62 million committed to their 2020-21 roster and nearly $50 million for the year after.

[ProHockeyTalk’s 2019 NHL free agency tracker]

That is a lot, and they not only have to worry about re-signing their superstars, but also filling out the remainder of the roster around them.

When it comes to prioritizing between Backstrom and Holtby the most sensible investment would seem to be Backstrom. He is a No. 1 center, still one of the best players in the world, and should continue to be a top-line performer into his 30s.

Will he decline some? Almost certainly. But what he gives the Capitals will still be better than the alternatives they might realistically be able to acquire.

That leaves Holtby. The problem the Capitals will have with Holtby is you already saw what his next contract might look like this summer when Sergei Bobrovsky signed with the Florida Panthers. That is going to be a massive contract to squeeze in under the cap when taking into account Backstrom’s next deal (which will probably be a raise, and maybe a significant one, from his current contract) and the eventual extension for Ovechkin (almost certainly $10 million-plus per season).

The only real to realistically do that is going to be shipping out another significant player in a trade.

Tom Wilson? T.J. Oshie? Dmitry Orlov? Or perhaps a combination depth players that are signed to term. The Lars Eller, Hagelin, and Panik trio will combine for $9 million against the cap in each of the next four seasons, all for depth players well into their 30s. Will that be the best use of salary cap space? (This is the risk with signing depth players to long-term contracts.)

But that is IF the Capitals want to make that sort of a commitment to Holtby.

He has been one of the best goalies in the league during his career and is still capable of shining in big moments and carrying the team when he is on top of his game. But over the past two seasons (and including the Stanley Cup year, when he did not even enter the playoffs as the starter) those moments have not been as frequent. He has started to shown signs of slowing down, and investing a seven-or eight-year contract into a goalie that will be 31 years old in the first year of his next deal could be too big of a risk.

If the Capitals have to move on from one of their big-three, Holtby is the most logical choice. He is the one that is probably least likely to retain most of his current value in future seasons, and even though he has been a top-tier goalie for so many years he is also probably the one they have the best chance of replacing.

The Ovechkin, Backstrom, and Holtby era has been an incredible success in Washington, winning two Presidents’ Trophy and a Stanley Cup all in the past four years.

But with their current contracts coming to an end it is entirely possible that one of them — probably Holtby — will be finishing their career in a different uniform barring some other significant change elsewhere on the roster.