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Although the Capitals are in the midst of their midseason bye week, the team's hockey operations department is still very much on the clock. For the second time over All-Star weekend, Washington has signed a player to a multi-year contract extension. On Saturday night, the Caps announced that they have come to terms with left wing Sonny Milano on a three-year contract extension that will carry an annual salary cap hit of $1.9 million.

On Friday, the Caps announced that they signed center Dylan Strome to a five-year contract extension with an annual salary cap hit of $5 million. Like Strome, Milano is a former first-round draft choice in his mid-20s who played for a couple of NHL clubs prior to arriving in Washington this season. And like Strome, Milano found the District enough to his liking in his first season here that he has inked a multi-year deal to remain with the Caps.
The 16th overall pick in the 2014 NHL Draft, Milano was chosen by the Columbus Blue Jackets and he got his first taste of the NHL with the Blue Jackets as a 19-year-old, getting into three games late in the 2015-16 season. Later that same spring, he was a member of the Calder Cup champion Lake Erie Monsters squad that swept aside Washington's Hershey Bears AHL affiliate in the Calder Cup Final series.
Following another season in the AHL, Milano notched 14 goals and 22 points in 55 games with Columbus in 2017-18 in his first extended stretch in the NHL. He spent most of his time in the Blue Jackets' organization yo-yoing between Columbus and Cleveland, and his final season in Ohio's capital city was the only one in which he did not also spend time in the AHL. That was 2019-20, the season in which the Jackets swapped him to Anaheim at the trade deadline, getting Devin Shore in return. Shore's Columbus career lasted six games.
Milano made a brief splash with Anaheim after the deal, putting up five points (two goals, three assists) in nine games before the pandemic set in and halted the '19-20 regular season in its tracks. An upper body injury and a concussion limited him to just six games with the Ducks in 2020-21, but he had his best NHL season with Anaheim in 2021-22, posting 34 points (14 goals, 20 assists) in 66 games, matching or establishing career highs in goals, assists and points.
Similar to Strome's situation in Chicago, the Ducks did not issue a qualifying offer to Milano following his breakout season, and he became a free agent. But unlike Strome, he wasn't able to land an NHL deal. Milano went to camp on a pro tryout agreement with Calgary last fall, but when the Flames opted not to sign him, he was again in limbo.
Having lost a pair of depth wingers (Brett Leason to Anaheim and Axel Jonsson-Fjallby to Winnipeg) to preseason waiver claims and losing another winger Connor Brown to long term injury early in the regular season, the Caps opted to sign Milano to a one-year deal to help replenish their depth.
After a quick stint with AHL Hershey to get up to speed, Milano was recalled by the Caps in early November and he has been a fixture in their middle six ever since. Despite not spending training camp with the Caps, he caught onto the system quickly and has played steady and consistent hockey since his arrival. Milano played on Washington's second power play unit for much of the first half of the season, showing a knack for entering the zone with speed and a willingness to go to the net. He has not gone more than four games without recording a point this season, and he is eighth on the team in scoring despite missing the first 13 games of the season.
All eight of Milano's goals have been scored at even strength, and he ranks third on the team in even-strength goals. With 22 points (eight goals, 14 assists) in 40 games since making his Caps debut on Nov. 5, he ranks fourth on the team in goals and sixth in scoring over that stretch.
Milano is one of nine forwards Washington has under contract for next season, and he and Nic Dowd are the only two of those nine whose contracts carry an average annual value of less than $5 million. The total average annual value of those nine forwards under contract for next season is just a shade above $50 million, which is only about $7 million less than the Caps' entire forward group from this season.
Washington has cost certainty with its goaltending tandem in the near term, but it will need some cap space with which to assemble its blueline for next season. As of right now, John Carlson is the only Caps defensemen under contract for next seasons. With the salary cap again expected to be relatively flat for the 2023-24 campaign, we are likely to see some adjustments in the team's personnel up front between now and the summer ahead.