why do I always trade the same players

Maybe because they're slightly average guys, making more than the minimum, with not much market value and Toronto is capped out?

I like Dermott and at 1.5mil not overpaid, but hes a 3rd pairing guy PERIOD, whos not a physical crease clearer or a puck rushing pt producer. Hes nice but ultimately average, hes a third pairing guy and you dont need anything flashy from a 3rd pairing guy, but with his NHL minutes dwindling and no sign of him being better than he is now, his value isnt great enough to move him, if only for cap reasons. (For example: Keith Yandle, Bogosian, Luke Schenn, etc...all make almost half of what Dermott makes)

Engvall at 26 yrs old, is a pretty borderline NHLer and almost every team has 1 or 2 that play well enough to stay in the league, but aren;t a reliable top 9 guy that brings defense or hitting or point production. Engvall is getting 1.25mil, Derrick Brassard, for example, is getting 825k and is a more reliable team veteran and pt producer. (Cedric Pacqueete gets lge minimum as does Mattheiu Perreault, but they bring physicality/defense or speed/offense). Engvall does alot of thing well, big, not slow, etc... but overall: average performer.

As for Kerfoot, I'd put him as the 6th or 7th most talented forward, yet at 3.5mil his production does not match his salary and hes next in the long line of Toronto midlevel salaries moved out (Kadri, Kapanen, Johnson, Gardiner, Hyman, etc...) because the team is salary top heavy...

I'd assume it probably revolves around the fact that they're the only 4 moveable players in the lineup.

Could someone else get moved? Sure! But are you going to dismantle your D-core by moving Holl? No, because you'd be digging a hole to fill another. Are you going to trade any of the recent signings like Ritchie, Kase, Bunting, Mrazek, Spezza, Simmonds or Kampf? No, that'd be illogical because, aside from Simmonds/Spezza, if another team wanted those guys badly enough, they would have either just offered them an equal or slightly greater contract. Are you going to move any of the big 4? No, because you're a playoff contender and moving your best players isn't something that contenders do. Are you going to move Rielly? No, because he's a free rental, and you're a playoff contender. Yep, you're probably going to lose him for nothing in the offseason, but you need him right now. Are you going to move prospects? IMO, you need all the ELC's that you've got right now, and moving forward.

So, who does that leave us with? Engvall, Dermott, Mikheyev, and Kerfoot, and zero cap space. Kerfoot could probably be used to balance the salaries in a potential trade, but really, I doubt there's a long list of teams out there with players that are cheap enough, and high end enough to be a reasonable upgrade on him, especially without going crazy overpaying for that player.

Agreed-They're players that every team in the league already has. Is there some value there? Maybe, but IMO, Envall passes through waivers untouched and Dermott makes it through half the league before being picked up to be a 6th/7th dman. They're not bad, but they're also not particularly good.

"why do I always trade the same players". Cause so many people can't construct a roster. Seems liker so many Leafs fans, think Dermot, Engvall, Mikheyev and Kerfoot are the cause of the Leafs problems have to moved, often for other teams bottom enders. Really what is the point?
Leafs shouldn't be trading Dermot without getting an NHL Dman in return.

Really its ignoring the issue:

Think back to how many "mid level" salaries have been moved/left to afford the current salary structure?

Kadri, Kapanen, Johnsson, Andersen, Gardiner, Hyman, probably Reilly were all in that 2-5mil range. Not to say they've gone on to bigger or better things, but put it this way, is Toronto a better team with Tavares or with Kadri AND Kapanen AND Hyman?

Those 3 make just a bit more than Tavares alone. And its not just that, its the ability to move individual pieces/address multiple lines/positions to create cap space or make trades.

Its funny that the tradition continues with moving kerfoot 3.5mil, engvall 1.25, mikheyev 1.65 and Holl 2mil, instead of maybe looking at a Muzzin 5.6 or the big 4.