NHL Notebook: Is Bobby Ryan worth a look for Bruins; why Craig Smith could be the steal of this top-heavy UFA class

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After breaking down the pending free agents that Boston should steer clear of this offseason in our last weekend notebook, let's focus on a few names that Boston should keep tabs on when free agency opens on Oct. 9th. We'll focus on a pair forwards in this segment, with a breakdown of free-agent defensemen dropping later this week. In terms of targets, we're also going to save our thoughts on the feasibility of no-brainer, big-fish acquisitions like Taylor Hall for later this week. This is a more a look at some middle-six or value free-agent targets that may not steal headlines, but could provide great value as Don Sweeney looks to navigate this offseason with a flat salary cap upper limit of $81.5 million. 

Bobby Ryan, Right Wing

The NHL buyout window is officially open — signaling close to two weeks in which teams can jettison albatross contracts and free up cap space in anticipation of free agency and the perils that lie ahead with a stagnant cap ceiling. 

And yet, despite the number of likely slam-dunk candidates (Henrik Lundqvist) when it comes to buyouts, the first name to hit the transaction wire was quite the shock — considering said player is the reigning Masterton Trophy winner.

The Ottawa Senators announced Friday morning that winger Bobby Ryan was placed on waivers for the purpose of buying out the final two years of the seven-year, $50.75 million contact he inked back in October 2014. Ryan, 33, is coming off of a season in which he tallied five goals and eight total points over 24 games — with the veteran winger taking an extended leave of absence in November to join the NHL/NHLPA player assistance program due to alcohol abuse.

Ryan eventually returned to the Senators in late February, scoring a hat trick in his first home back in Ottawa on March 2nd. Given his efforts toward overcoming these struggles away from the rink, his willingness to share his own story with the public and his inspiring play down the final stretch of the Senators' season, it didn't come as much of a surprise that Ryan was named the 2019-20 Masterton Trophy winner — given annually to the player who best exemplifies the qualities of perseverance, sportsmanship and dedication to hockey.

And yet, even with Ottawa in line to add a few stagnant contracts just to hit the salary cap floor for the upcoming 2020-21 campaign, Eugene Melnyk and the Sens opted to shave off about $3.6 million in Ryan's annual cap hit by way of this buyout — which spreads a portion of his remaining salary out over four seasons, while making the veteran an unrestricted free agent.

In a top-heavy cluster of free agents inundated with (expensive) top prizes like Taylor Hall, aging veterans and empty stat-stuffers like Mike Hoffman — Ryan stands as an intriguing option as a low-risk, potentially high-reward addition for a team in desperate need of offensive production in the middle six.

Sound like any club you know?

So would taking a flyer on a player like Ryan be worth it for Boston?