Most blue chip prospects are going to sign an ELC as soon as they can, especially if they are drafted out of junior, so getting them under contract after drafting them isn't usually an issue. It becomes a little trickier with college and university players who are ready because there is an incentive to continue their education. If you are burning a 1st round pick, I think you need to weigh that risk and get a good feel for what the intentions of the player are before you draft them.
The key here is asset management and what happens with that 2nd contract. If the player is trending to become a star and you can't get them signed to a long term deal, you need to flip the asset. To be fair, that isn't just a thing with American players. A lot of players regardless of where they are from, may not want to commit to giving up UFA years. It's just important for teams like the Flames to manage the assets well if that is case. With Tkachuk, it seems like Treliving was honestly caught off guard that he wouldn't be signing long term after the bridge and was then forced into a very limited trade market. It shoulldn't get to that point. Same thing with Gaudreau. The player said as early as August before the season began that he didn't want to talk about an extension until after the next season, and that should have been a huge red flag. Some teams can take the risk to walk the player to the end of the season, but small market Canadian teams can't take that risk. You have to get in front it quicky.
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"A pessimist thinks things can't get any worse. An optimist knows they can."
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