Both defensemen have spent an extended period of time with the St. Louis Blues and Boston Bruins, respectively, but they may be courted by franchises looking to make upgrades in free agency.
Pietrangelo may be in a tough negotiating spot with the Blues since the franchise has spent a good chunk of change on the position already.
Boston could be in a better position to fend off potential suitors for Krug since it carries more salary-cap space than the Blues.
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A handful of factors could make negotiations between Pietrangelo and the Blues difficult.
The Blues already have two defensemen scheduled to make over $5.5 million next season, and they recently signed Marco Scandella to a four-year extension worth $13 million.
As Jim Thomas of the St. Louis Post-Dispatch pointed out, Blues general manager Doug Armstrong may feel comfortable with Colton Parayko, Justin Faulk and Scandella leading the depth chart with prospects filling in the depth chart beneath them.
"With Scandella reupping, maybe Armstrong feels the club can remain a Cup contender without Pietrangelo, especially with defensemen like Mikkola, Perunovich and Walman in the pipeline," Thomas wrote.
Sportsnet's Elliotte Friedman detailed where the negotiations stood during a radio appearance in April:
"I don't think (Armstrong)'s willing to go to market. I don't think there's been a lot of dialogue on this one this year. I think there's been on again and off again negotiations. I believe the Blues made it clear they were willing to go around Ekman-Larsson and Ekman-Larsson is eight times 8.25 and I think the Blues are maybe willing to go a little bit higher because he's their guy, he's their captain, but I don't think they were willing to go into the nines or anything more than that."
Arizona's Oliver Ekman-Larsson, whose deal was referenced by Friedman, signed an eight-year extension worth over $8 million per year.
Only four defensemen currently make over $9 million per season, but Pietrangelo could make a case that he deserves that level of a contract.
The 30-year-old has increased his offensive production over the last four seasons. He scored a career-high 16 goals and recorded his second-best point total this season.
St. Louis has to weigh how much it values Pietrangelo's leadership and prowess on both ends of the ice when it makes an offer to him.
Pietrangelo is on the final season of a seven-year, $45 million deal, and if he wants a long-term contract, he should ask for more in negotiations.
It will not be easy for the two sides to come to an agreement, but if the Blues are willing to pay in the range of $8 million per year, a deal could get done since the two parties have achieved plenty of success together.
Prediction: Pietrangelo re-signs with Blues.
Krug sits in a similar position as Pietrangelo at 29 years old and as a consistent provider in the offensive zone.
The main difference between the two is Krug is on the back end of a four-year, $21 million contract that pays him over $1 million less than Pietrangelo for the 2019-20 season.
Krug was one point away from his fourth straight 50-point campaign, and he should draw interest from all over the league.
Sportsnet's Eric Engels stated "it's a probability the Canadiens would go hard after Torey Krug."
Montreal is currently one of 15 teams with $20 million or more in salary cap space open for the 2020-21 season.
Ottawa and Detroit, who have the most cap space, might prepare runs at the top free agents as well to boost their respective stocks in the Eastern Conference.
When it comes to Montreal, that could be a tough sell for Krug since the Canadiens and Bruins are long-time rivals.
There is also a chance the Canadiens and others do not get a shot to offer deals to Krug, as Boston owns $22 million in cap space and could make a healthy offer to the 29-year-old.
Prediction: Boston re-signs Krug before he hits open market.
Follow Joe on Twitter, @JTansey90
Statistics obtained from Hockey Reference
Contract information obtained from Spotrac