Where to send Liles??

[Britishbulldog]

I don't pretend to know the Marlies all that well, but I have trouble believing at least two of the overpayments -- Orr and Fraser, totaling about $1m over what those roster spots would cost with AHL promotions -- couldn't be replaced internally.

Actually it wasn't the players like Orr who are taking 1.4% of the cap space or Fraser who takes 1.9% who I am worried about.

My concern is that the Leafs are typically going after players that have established who they are as a player and can demand a value based on that.  A team only needs to add 1 or at most 2 young players a season to keeps a team salary in check.  Teams like St. Louis, Detroit, NYR and Montreal have players like Subban, Del Zotto, etc playing great hockey as youngsters and have gotten 4 or 5 years out of their rookies before the big payday.  Toronto has a single shortened season out of Kadri and it appears that Kadri is expecting HUGE money for those few games...... and I think the media and fans are expecting it as well.  Every other forward on the Leafs have gotten a contract reflecting their value in the league at time of signing.

It looks like it might work for the Leafs with Gardiner atleast as he is signed another year but I fear that the Leafs brass and media/fans will expect to pay him Doughty money rather than Subban money on his 2nd contract.

 

[leafplasma]

What I have been concerned with since Burke has been here and it has even escalated more this Spring and Summer is the allocation of money.  When a team is close to the cap limit than theoretically it should basically match their place in the standings.  The only way it appears to beat the system is by having players on ELCs and 2nd contracts that perform as well as comparable veterans.  I think that is what Nik was concerned about with lower 6 players needing to be re-signed to larger contracts when they should be getting replaced by younger (read:cheaper) players in the system.  Toronto doesn't seem to have those players ready from the last 4 drafts that Burke presided over.

I don't pretend to know the Marlies all that well, but I have trouble believing at least two of the overpayments -- Orr and Fraser, totaling about $1m over what those roster spots would cost with AHL promotions -- couldn't be replaced internally.

Devane and Broll are not ready so no.  In Broll I think the Leafs have plans on making him more of a player than Orr or Fraser could ever be so he needs the time to develop.  Ross is a Tucker type so he can't do the Orr/Fraser thing either.  Still think it is crazy to have both guys though on the roster but I would rather one of them in the press box than one of our developing youth though and I am not sure what Bodie or Smith bring to the table  that would warrant them more valuable with the big club than one of Orr or Fraser so who knows.

 

[mr grieves]

My concern is that the Leafs are typically going after players that have established who they are as a player and can demand a value based on that.  A team only needs to add 1 or at most 2 young players a season to keeps a team salary in check.  Teams like St. Louis, Detroit, NYR and Montreal have players like Subban, Del Zotto, etc playing great hockey as youngsters and have gotten 4 or 5 years out of their rookies before the big payday.  Toronto has a single shortened season out of Kadri and it appears that Kadri is expecting HUGE money for those few games...... and I think the media and fans are expecting it as well.  Every other forward on the Leafs have gotten a contract reflecting their value in the league at time of signing.

Ah, yes, I see. That seems a problem. Most of the unestablished, underpaid talent the team has had was brought in by trade and so further into their careers than would be ideal. Franson, Grabo, MacArthur, Lupul, JVR, and Kessel were all being paid somewhat below what they were providing (or, in Franson's case, provided when they played) for a season or two. But that's not long enough, and the Leafs now seem down to two of those contracts, one after this season.

 

[princedpw]

There are a number of things Philly management has done better than Leafs management recently.  One of them is asset management.  They signed players to long, expensive contracts (Carter, Richards) to retain them as assets.  They then converted those assets in to young, good-for-the-cap pieces (Schenn, Couturier, etc.). In contrast, the Leafs had some good assets (though not as highly regarded as Carter, Richards) such as Grabbo and MacCarthur (perhaps Liles pre-resigning could be included) and lost them for no return.  Negative return really because Grabbo's buyout uses a "buyout" asset.

Of course Bryz was a huge blunder on Philly's part.

I understand people might see LA winning the cup and see Philly missing the playoffs.  However, I don't think that is due to their forwards.  The problem is they lost Pronger and their defense sucks.

 

[Zee]

There are a number of things Philly management has done better than Leafs management recently.  One of them is asset management.  They signed players to long, expensive contracts (Carter, Richards) to retain them as assets.  They then converted those assets in to young, good-for-the-cap pieces (Schenn, Couturier, etc.). In contrast, the Leafs had some good assets (though not as highly regarded as Carter, Richards) such as Grabbo and MacCarthur (perhaps Liles pre-resigning could be included) and lost them for no return.  Negative return really because Grabbo's buyout uses a "buyout" asset.

Of course Bryz was a huge blunder on Philly's part.

I understand people might see LA winning the cup and see Philly missing the playoffs.  However, I don't think that is due to their forwards.  The problem is they lost Pronger and their defense sucks.

In addition to sending Carter and Richards away who proceeded to win the Cup immediately the same season, they also traded away the goalie that just won the Vezina and instead signed Bryz to a gazillion year contract only to buy him out.  I'd take the Leafs moves anyday.

 

[Bender]

There are a number of things Philly management has done better than Leafs management recently.  One of them is asset management.  They signed players to long, expensive contracts (Carter, Richards) to retain them as assets.  They then converted those assets in to young, good-for-the-cap pieces (Schenn, Couturier, etc.). In contrast, the Leafs had some good assets (though not as highly regarded as Carter, Richards) such as Grabbo and MacCarthur (perhaps Liles pre-resigning could be included) and lost them for no return.  Negative return really because Grabbo's buyout uses a "buyout" asset.

Of course Bryz was a huge blunder on Philly's part.

I understand people might see LA winning the cup and see Philly missing the playoffs.  However, I don't think that is due to their forwards.  The problem is they lost Pronger and their defense sucks.

Grabbo not getting signed yet tells me all I need to know about his value.

Sent from my SGH-T999 using Tapatalk 2

 

[bustaheims]

Grabbo not getting signed yet tells me all I need to know about his value.

I wouldn't read anything into that. A big part of the reason he's not signed yet was the timing of how everything played out. He got married the same weekend he became a free agent. He clearly had other things on his mind and decided on a team and contract was low on the list for him. After the early feeding frenzy, most of the available money was gone, and, Grabovski's situation has left him out in the cold for now.

 

[Jalili]

There are a number of things Philly management has done better than Leafs management recently.  One of them is asset management.  They signed players to long, expensive contracts (Carter, Richards) to retain them as assets.  They then converted those assets in to young, good-for-the-cap pieces (Schenn, Couturier, etc.). In contrast, the Leafs had some good assets (though not as highly regarded as Carter, Richards) such as Grabbo and MacCarthur (perhaps Liles pre-resigning could be included) and lost them for no return.  Negative return really because Grabbo's buyout uses a "buyout" asset.

Of course Bryz was a huge blunder on Philly's part.

I understand people might see LA winning the cup and see Philly missing the playoffs.  However, I don't think that is due to their forwards.  The problem is they lost Pronger and their defense sucks.

In addition to sending Carter and Richards away who proceeded to win the Cup immediately the same season, they also traded away the goalie that just won the Vezina and instead signed Bryz to a gazillion year contract only to buy him out.  I'd take the Leafs moves anyday.

Losing Chris Pronger is what especially did them in. I actually think they did well in what they got for Carter and Richards, but moreso Carter than Richards. However, both those moves were predicated on Pronger leading them for the next few years, which didn't go as planned.

But yeah, Philly's moves look counterintuitive at this point, because they went from being playoff fixtures to bottom feeders.

 

[Kin]

There are a number of things Philly management has done better than Leafs management recently.  One of them is asset management.  They signed players to long, expensive contracts (Carter, Richards) to retain them as assets.  They then converted those assets in to young, good-for-the-cap pieces (Schenn, Couturier, etc.). In contrast, the Leafs had some good assets (though not as highly regarded as Carter, Richards) such as Grabbo and MacCarthur (perhaps Liles pre-resigning could be included) and lost them for no return.  Negative return really because Grabbo's buyout uses a "buyout" asset.

Of course Bryz was a huge blunder on Philly's part.

I understand people might see LA winning the cup and see Philly missing the playoffs.  However, I don't think that is due to their forwards.  The problem is they lost Pronger and their defense sucks.

That still strikes me as largely revisionist history with regards to Carter and Richards though. They weren't re-signed so they could be retained as assets, they were re-signed because they were very good young hockey players who Philadelphia wanted to build around and they performed well after signing their new extensions(Richards with 66 points, Carter in the top 10 in goal scoring) and were able to be traded for the pieces you reference because they played well.

So that the Flyers were able to trade their highly performing players with big contracts and the Leafs weren't able to trade their severely underperforming player with a big contract seems only to reflect poorly on management from the basis of the decisions to give those guys the contracts in the first place. That would be an absolutely fair thing to criticize Leafs management on if it weren't for the fact that the guy who made that decision got fired before the season began. 

As for Mac I think that you're displaying a bit of tunnel-vision there when it comes to the idea of asset management. They didn't "lose Mac for nothing", they kept him on the team for the duration of his contract through which he provided a certain level of value to the team. He helped them win games. He played a role in getting them into the playoffs and then, once in the playoffs, helped them there as well. When you're weighing the value of MacArthur from a "asset" standpoint you can't just ignore the value of him as a hockey player contributing to the team he's on. A second round pick, or whatever they might have fetched for him at the deadline, has to be weighed against the value of the effort he contributed while being on the team, either from a business standpoint or from a "winning hockey games is the whole point of this" standpoint.

 

[Kin]

Grabbo not getting signed yet tells me all I need to know about his value.

I wouldn't read anything into that.

Well, you have to read something into that. Clearly Grabo's value right now isn't high enough to cause a team with cap space, and there are teams out there with cap space, to look at him and whatever his asking price is and say that he's a good investment.

 

[moon111]

I think Liles is to Gardiner and Reilly what Connolly was to Kadri.  A reason not to rush kids into the NHL.  The Leafs are willing to take the time to let kids, no matter how good they are, develop further.

 

[bustaheims]

Well, you have to read something into that. Clearly Grabo's value right now isn't high enough to cause a team with cap space, and there are teams out there with cap space, to look at him and whatever his asking price is and say that he's a good investment.

I'm not sure I agree. I look at the teams that really have cap space available, and what I see are teams that likely don't have the financial ability to significantly exceed their current payroll - these are teams that are, in their own way, capped out.

 

[CarltonTheBear]

Well, you have to read something into that. Clearly Grabo's value right now isn't high enough to cause a team with cap space, and there are teams out there with cap space, to look at him and whatever his asking price is and say that he's a good investment.

I'm not sure I agree. I look at the teams that really have cap space available, and what I see are teams that likely don't have the financial ability to significantly exceed their current payroll - these are teams that are, in their own way, capped out.

Not only that, but a lot of the teams that do have cap room are also somewhat set at centre. He would probably be best off taking a very small one-year contract with a team like Buffalo or New Jersey where he could potentially be their top centre and trying the free agency market next season when teams have more wiggle room.

 

[princedpw]

That still strikes me as largely revisionist history with regards to Carter and Richards though. They weren't re-signed so they could be retained as assets, they were re-signed because they were very good young hockey players who Philadelphia wanted to build around and they performed well after signing their new extensions(Richards with 66 points, Carter in the top 10 in goal scoring) and were able to be traded for the pieces you reference because they played well.

I didn't mean to make too much of the "why" they were resigned.  They simply were re-signed and that was good as it retained them as assets (ie, as valuable players).  Then Carter, for instance, was traded so shortly after being re-signed that his new no-trade clause didn't yet kick in.  I guess I'm just pointing out that Holmgren successfully extended the life of an asset and then converted that asset (UFA-age, top-end forward), which he had an amazing abundance of, in to another asset (rookie/future).

I don't think the Leafs are good enough right now.  You will probably agree!  One way to do it is to "roll over your roster"  (not a new idea of course) by selling off some of the older guys at key times for more futures.  Then maybe the next offseason, buying more older guys as free agents as well as using your (hopefully many) draft picks wisely to stock for the future.

So that the Flyers were able to trade their highly performing players with big contracts and the Leafs weren't able to trade their severely underperforming player with a big contract seems only to reflect poorly on management from the basis of the decisions to give those guys the contracts in the first place. That would be an absolutely fair thing to criticize Leafs management on if it weren't for the fact that the guy who made that decision got fired before the season began. 

It is definitely irritating that the Burke-Nonis transition got in the way.  I am a proponent of trying to identify the best possible GM, paying him money that no other team in the league will match and keeping him for a very long time -- a decade.  Given the current state of the Leafs franchise, we've got to make sure GMs do not have short-term incentives, which is what frequent hirings and firings do.  I didn't like the Burke firing (but I'm also a little biased there and swayed by things Burke was doing unrelated to the team performance).

Briefly, and I know it has been rehashed ad naseum so I apologize for continuing this somewhat boring line of discourse but, Grabbo played incredibly well for several years before his contract was given out.  Subjective evaluation backs it up.  And I trust the stats guys analysis (which I know you don't) more than my own ad hoc subjective evaluation (or yours) and their stats uniformly point to fabulous performance.  Something went wrong last year -- he was worse in every way.  I can't explain it because I didn't notice a decrease in speed or hands or desire or heart or strength or agility.  However, I don't think a hockey player will just lose all his talent in a year and especially don't trust evaluation in the shortened, weird-start lockout year.

So, yes, the Leafs couldn't trade him this offseason.  I accept that.  So don't destroy the asset this specific offseason during a cap crunch.  I would have kept him and played him with Kessel and JVR next year.  They appear to be ridding themselves of a valuable asset at the worst time possible when it has the lowest value.  And it's killing me that they are replacing this asset with a guy all the stats people universally say is an absolutely horrid, horrid player.  I can't help but trust those stats guys more than subjective evaluation.  Bozak is Komisarek #2 superficially hidden by the fact that he is playing with an elite, elite winger in Kessel. 

As for Mac I think that you're displaying a bit of tunnel-vision there when it comes to the idea of asset management. They didn't "lose Mac for nothing", they kept him on the team for the duration of his contract through which he provided a certain level of value to the team. He helped them win games. He played a role in getting them into the playoffs and then, once in the playoffs, helped them there as well. When you're weighing the value of MacArthur from a "asset" standpoint you can't just ignore the value of him as a hockey player contributing to the team he's on. A second round pick, or whatever they might have fetched for him at the deadline, has to be weighed against the value of the effort he contributed while being on the team, either from a business standpoint or from a "winning hockey games is the whole point of this" standpoint.

I'm going to ignore the "business standpoint" -- I don't care to speak to that.  I think the Leafs are sufficiently far from competing that they need to make some tough decisions .  Like if they don't want to use Mac going forward (and don't even play him that much ... did he get scratched in the playoffs?  I can't remember) then they should trade him to extend his value in to the future, even if it may mean a shorter term hit.

Having said that, a winger like Mac isn't nearly as valuable as a 2-way center like Grabbo and so I care a little less there.

 

[TML fan]

They needed MacArthur for the playoffs. When exactly were they going to trade him?

 

[Kin]

I'm not sure I agree. I look at the teams that really have cap space available, and what I see are teams that likely don't have the financial ability to significantly exceed their current payroll - these are teams that are, in their own way, capped out.

But I think the idea that these teams aren't able to spend the extra money is fundamentally flawed. There isn't a team in the NHL that's so Cash poor that they couldn't choose to spend an extra four million dollars this year if they thought it was a good investment. Yes, teams like the Avs, Islanders and Sabres might be choosing to keep to an internal cap but if we even vaguely buy the premise that hockey players get paid the way they do because what they contribute to their teams generates an equal or, ideally, greater amount of revenue by means of making the teams better then Grabo not getting a contract is a pretty firm statement that all of those teams are taking a look at him and saying that what he's looking for in salary make him a bad investment.

Like I said, that's not everything and I'd guess that a fair argument can be made that no mid-tier players like Grabo really generate enough money to be worth their contracts but the fact that the teams with cap space, all of whom could afford Grabo in a nuts and bolts sense, are looking at him and deciding that paying him the salary that he wants would lose them money(or at least not make them money)...that's something.

 

[Kin]

I didn't mean to make too much of the "why" they were resigned.  They simply were re-signed and that was good as it retained them as assets (ie, as valuable players).  Then Carter, for instance, was traded so shortly after being re-signed that his new no-trade clause didn't yet kick in.  I guess I'm just pointing out that Holmgren successfully extended the life of an asset and then converted that asset (UFA-age, top-end forward), which he had an amazing abundance of, in to another asset (rookie/future).

It's an important distinction though. Looking at Carter/Richards and the frankly bizarre way in which they left the Philadelphia and comparing it to what's happened in Toronto seems unfair if only because that situation is so unique. Holmgren didn't make a risky or hard decision in trying to re-sign two players who weren't yet 26 and having terrific starts to their career. If you have players who are that good and that young you try to re-sign them and, because they weren't yet pending UFA's, they had leverage.

To compare that to a situation like MacArthur, where the team genuinely had to ask themselves if a pending UFA who probably isn't good enough for a top 6 but not really versatile enough to be on a really good third line(which is more or less the same situation Grabo was in after last year) was worth signing with the intention of actually using him on the hockey team seems a little shaky.

It's not a video game. You can't sign guys with the intention of trading them. Holmgren probably did real damage to his ability to negotiate with any good RFA's he has in the future because of his decision to "roll over" Carter and Richards so soon after signing them to long term deals.

Briefly, and I know it has been rehashed ad naseum so I apologize for continuing this somewhat boring line of discourse but, Grabbo played incredibly well for several years before his contract was given out.  Subjective evaluation backs it up.  And I trust the stats guys analysis (which I know you don't) more than my own ad hoc subjective evaluation (or yours) and their stats uniformly point to fabulous performance.  Something went wrong last year -- he was worse in every way.  I can't explain it because I didn't notice a decrease in speed or hands or desire or heart or strength or agility.  However, I don't think a hockey player will just lose all his talent in a year and especially don't trust evaluation in the shortened, weird-start lockout year.

I don't think that a player has to lose his talent, if talent is a quantifiable thing, for him to start playing worse. There are lots of things that can affect how a player plays, including whether or not he can adequately fill the roll his coach is asking him to.

Regardless, it's beside the point. Nonis tried to trade Grabo, he couldn't. The reason he couldn't is because of Grabo's lousy performance. Again, the point there wasn't to rehash whether or not Randy Carlyle giving Grabo 8% fewer Offensive Zone starts than Bozak got was the 21st century sabotage equivalent of Tanya Harding paying someone to hit him in the knee, it was to highlight the difference between the ease in trading a player who is playing well and one who isn't. It's very fine and good to say that if you were the GM you would have just held on to Grabo, fired the cup winning coach who didn't want to play him on the 1st line(and dealt with whatever ensuing mess that might have created) and waited around for him to start playing better but that's like saying that a poker player's strategy was a failure because he didn't go for the nickel slots instead.

As to the central premise though I remain convinced that if holding onto to Grabo, paying him what he was being paid over Bozak(which would make the cap crunch worse, not better) and giving him a big chunk of playing time  was the way to go that someone in the league who ran a team would have seen that value in him and offered up...oh....a 7th round pick for him.

I mean, you could argue that nobody did because his contract was onerous and they knew the Leafs wanted to dump him which would mean they could get him cheaply as a UFA but...well, nobody seems to be rushing over themselves to do that either.

I'm going to ignore the "business standpoint" -- I don't care to speak to that.  I think the Leafs are sufficiently far from competing that they need to make some tough decisions .  Like if they don't want to use Mac going forward (and don't even play him that much ... did he get scratched in the playoffs?  I can't remember) then they should trade him to extend his value in to the future, even if it may mean a shorter term hit.

But as I sort of alluded to I think there's a perception, make of it what you will, that there is actual value in winning hockey games. Not just from some sort of easily dismissed competitive angle but from an actual "this creates a positive atmosphere" or "this helps us attract and retain other players" or "playing in the playoffs, even if you're not a contender gains the players on your team experience which cannot be obtained in any other fashion" sense.

It's nebulous, I know, maybe it might even qualify as the sort of "intangible" that those advanced stats guys will laugh at but I think if you give that even the tiniest bit of weight that the decision of weakening the team for the fairly minimal return Mac could bring....it isn't even so much about right and wrong as it is about making a mountain out of a molehill.

 

[mr grieves]

Briefly, and I know it has been rehashed ad naseum so I apologize for continuing this somewhat boring line of discourse but, Grabbo played incredibly well for several years before his contract was given out.  Subjective evaluation backs it up.  And I trust the stats guys analysis (which I know you don't) more than my own ad hoc subjective evaluation (or yours) and their stats uniformly point to fabulous performance.  Something went wrong last year -- he was worse in every way.  I can't explain it because I didn't notice a decrease in speed or hands or desire or heart or strength or agility.  However, I don't think a hockey player will just lose all his talent in a year and especially don't trust evaluation in the shortened, weird-start lockout year.

I don't think that a player has to lose his talent, if talent is a quantifiable thing, for him to start playing worse. There are lots of things that can affect how a player plays, including whether or not he can adequately fill the roll his coach is asking him to.

Regardless, it's beside the point. Nonis tried to trade Grabo, he couldn't. The reason he couldn't is because of Grabo's lousy performance. Again, the point there wasn't to rehash whether or not Randy Carlyle giving Grabo 8% fewer Offensive Zone starts than Bozak got was the 21st century sabotage equivalent of Tanya Harding paying someone to hit him in the knee, it was to highlight the difference between the ease in trading a player who is playing well and one who isn't. It's very fine and good to say that if you were the GM you would have just held on to Grabo, fired the cup winning coach who didn't want to play him on the 1st line(and dealt with whatever ensuing mess that might have created) and waited around for him to start playing better but that's like saying that a poker player's strategy was a failure because he didn't go for the nickel slots instead.

As to the central premise though I remain convinced that if holding onto to Grabo, paying him what he was being paid over Bozak(which would make the cap crunch worse, not better) and giving him a big chunk of playing time  was the way to go that someone in the league who ran a team would have seen that value in him and offered up...oh....a 7th round pick for him.

I mean, you could argue that nobody did because his contract was onerous and they knew the Leafs wanted to dump him which would mean they could get him cheaply as a UFA but...well, nobody seems to be rushing over themselves to do that either.

Apart from what sort of asset Grabovski was before he was re-signed or at the beginning of the season given the Leafs' unsettled management and the lockout, was at the end of this one given his poor performance and/or misuse, is now as a UFA given his parting shots and the cap, or could've been had he been retained, whatever team ends up signing him for $3.5m or $4m or $4.2m (the Tyler Bozak special) is going to get a very good hockey player at a very good price. I think, at the end of the day, why no one offered a 7th round pick or grabbed him off waivers, how long it took him to sign, etc. aren't going to mean much. Grabovski scoring 25 goals and 55 points on a cheap contract is going to be the main thing that people look to when talking about his value.

As for the bolded bit, especially regarding the cap crunch, I think everyone who holds the view of Grabo and the off-season moves that princepw seems to sees the Bozak-over-Grabo move in the context of others Nonis made. Bozak wasn't chosen over Grabo for cap relief but to clear the space needed to sign Clarkson. If the moves were about cap relief, then the cap with Bozak + Clarkson (about $9.5m hit) wouldn't be about $1m closer than with Grabo at $5.5m and some borderline top-6 winger for around ~$3m (say, MacArthur). These were hockey decisions, and maybe the team is a bit better with the two Nonis chose. The fancy stats people seem to think not. I certainly have my doubts. We'll see next season.

 

[princedpw]

I'm not sure I agree. I look at the teams that really have cap space available, and what I see are teams that likely don't have the financial ability to significantly exceed their current payroll - these are teams that are, in their own way, capped out.

But I think the idea that these teams aren't able to spend the extra money is fundamentally flawed. There isn't a team in the NHL that's so Cash poor that they couldn't choose to spend an extra four million dollars this year if they thought it was a good investment. Yes, teams like the Avs, Islanders and Sabres might be choosing to keep to an internal cap but if we even vaguely buy the premise that hockey players get paid the way they do because what they contribute to their teams generates an equal or, ideally, greater amount of revenue by means of making the teams better then Grabo not getting a contract is a pretty firm statement that all of those teams are taking a look at him and saying that what he's looking for in salary make him a bad investment.

Like I said, that's not everything and I'd guess that a fair argument can be made that no mid-tier players like Grabo really generate enough money to be worth their contracts but the fact that the teams with cap space, all of whom could afford Grabo in a nuts and bolts sense, are looking at him and deciding that paying him the salary that he wants would lose them money(or at least not make them money)...that's something.

I will grant you it means something: he's not a super-star.  But we knew that already.  I don't think your argument about investments is one of your better ones.  It can't be easy to estimate the expected revenue generated by any particular player in isolation.  It seems unlikely that GMs approach signing players with that kind of mindset as opposed to "I have a fixed X amount of dollars to build the best team I can."

 

[princedpw]

It's not a video game. You can't sign guys with the intention of trading them. Holmgren probably did real damage to his ability to negotiate with any good RFA's he has in the future because of his decision to "roll over" Carter and Richards so soon after signing them to long term deals.

People bring up the "damage to reputation" from time to time (we seen it before with "don't send him to the minors" or "don't buy him out even though he sucks") but it's pretty hard to quantify.  There seem to be many significantly bigger factors in where a player signs (money, location, team prospects).

If the Leafs were contenders then signing guys at the deadline and letting them go, which slowly drains your longer-term assets would be the way to go.  I don't think they are and should be doing the opposite.  Trade those guys you don't want to keep for futures, especially those guys like Mac that could have more value elsewhere than with you.

Briefly, and I know it has been rehashed ad naseum so I apologize for continuing this somewhat boring line of discourse but, Grabbo played incredibly well for several years before his contract was given out.  Subjective evaluation backs it up.  And I trust the stats guys analysis (which I know you don't) more than my own ad hoc subjective evaluation (or yours) and their stats uniformly point to fabulous performance.  Something went wrong last year -- he was worse in every way.  I can't explain it because I didn't notice a decrease in speed or hands or desire or heart or strength or agility.  However, I don't think a hockey player will just lose all his talent in a year and especially don't trust evaluation in the shortened, weird-start lockout year.

I don't think that a player has to lose his talent, if talent is a quantifiable thing, for him to start playing worse. There are lots of things that can affect how a player plays, including whether or not he can adequately fill the roll his coach is asking him to.

Regardless, it's beside the point. Nonis tried to trade Grabo, he couldn't. The reason he couldn't is because of Grabo's lousy performance. Again, the point there wasn't to rehash whether or not Randy Carlyle giving Grabo 8% fewer Offensive Zone starts than Bozak got was the 21st century sabotage equivalent of Tanya Harding paying someone to hit him in the knee, it was to highlight the difference between the ease in trading a player who is playing well and one who isn't. It's very fine and good to say that if you were the GM you would have just held on to Grabo, fired the cup winning coach who didn't want to play him on the 1st line(and dealt with whatever ensuing mess that might have created) and waited around for him to start playing better but that's like saying that a poker player's strategy was a failure because he didn't go for the nickel slots instead.

As to the central premise though I remain convinced that if holding onto to Grabo, paying him what he was being paid over Bozak(which would make the cap crunch worse, not better) and giving him a big chunk of playing time  was the way to go that someone in the league who ran a team would have seen that value in him and offered up...oh....a 7th round pick for him.

I mean, you could argue that nobody did because his contract was onerous and they knew the Leafs wanted to dump him which would mean they could get him cheaply as a UFA but...well, nobody seems to be rushing over themselves to do that either.

I'd be happy to fire the cup-winning coach and to snub my nose at the other GMs by retaining Grabbo. 

I'm going to ignore the "business standpoint" -- I don't care to speak to that.  I think the Leafs are sufficiently far from competing that they need to make some tough decisions .  Like if they don't want to use Mac going forward (and don't even play him that much ... did he get scratched in the playoffs?  I can't remember) then they should trade him to extend his value in to the future, even if it may mean a shorter term hit.

But as I sort of alluded to I think there's a perception, make of it what you will, that there is actual value in winning hockey games. Not just from some sort of easily dismissed competitive angle but from an actual "this creates a positive atmosphere" or "this helps us attract and retain other players" or "playing in the playoffs, even if you're not a contender gains the players on your team experience which cannot be obtained in any other fashion" sense.

It's nebulous, I know, maybe it might even qualify as the sort of "intangible" that those advanced stats guys will laugh at but I think if you give that even the tiniest bit of weight that the decision of weakening the team for the fairly minimal return Mac could bring....it isn't even so much about right and wrong as it is about making a mountain out of a molehill.
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I think this is your best argument.  I can believe there is value in having a winning team -- people want to go there.  And what happens to Mac is more molehill than mountain.  We'll see if Clarkson's and Bozak's contracts become more mountain than molehill in a few years.

One stats blogger has us finishing in the bottom 3 next year.  I myself am trying to prepare for a bottom-5-to-10 finish, which is kind of the worst spot:  Not bad enough to (have a good chance at) drafting a superstar that improves your team substantially in the long term; not good enough to get much fun out of the season.  We'll see.

I'm in full-on pessimism mode again.  Can you tell?