Basically Sam Lafferty, why are we constantly moving picks to replace the same type of players every single season? Zero direction or planning here.
To an extent i agree with you but its not apples to apples comparison.
Lafferty needed to be moved to be cap compliant at the beginning of the season. Lafferty is 29 years and a free agent in July. You traded him and got a 5th. You then took a 4th and a prospects to get a 24 year old player who is an RFA in Dewar. Although it cost slightly more, the Leafs got a more valuable asset with more control who was younger and the difference was a 5th for a 4th and prospects we arent sure will make an impact in the NHL. Seems inconsequential.
You also got ancillary value from opening up a roster spot at the beginning of the season. Guys like McMann, Holmberg, and Gregor got more playing time and you can see that they are NHL players who you can trust. Eventually someone's play is going to fall off or someone is going to get hurt, where one of those 3 guys will need to come back in the lineup. Value added.
When dealing with 30-40+ players in a season you cant plan every position down to a perfect science especially 4th liners. A lot happens in season especially when you have a salary cap hanging over your head, so you need to adapt and that is what Treliving did here. Saw an opportunity to get something for Lafferty, opened up playing time for others who ran with the opportunity an used similar draft capital you got for Lafferty to turn it into a younger player with control - maybe a better player.
Similar to Tampa trading Ross Colton to Colorado for a 2nd in the offseason because of the cap then using a 3rd and a good prospect to get Duclair less than a year later. Not something they wanted to do but had to and made the best of it.