LOL. Because I say this is the bleakest offseason ever, it means I love and am proud of the other offseasons?
Looking at each offseason "in the moment" without the benefit of hindsight, there was reason for some sort of optimism or hope nearly every summer. This year it's nothing but gloom. We need a fundamental change in the team and we're not getting it. All we've done is cast off the GM that had the ability to find value players to tinker around the edges, and brought in a guy who's made awful moves so far and has not signalled he's interested in any of the changes the team actually needs.
1993: The team had come out of nowhere to almost make the SCF with a rookie goaltender and we kept literally the entire roster together. Furthermore, we managed to come out of the season with TWO first round picks. Every reason to believe "Next year is our year"
1994: The Clark/Sundin trade was the biggest move, which was obviously polarizing but everyone could at least see how it could be a home run. We also picked up Mike Ridley, an excellent player, for nothing. The Mike Craig pickup was intriguing too. He sucked, but there was reason to believe that was a winning move. and Kenny Jonsson is probably going to step in and make the team. Optimism.
1995: Fletcher made a really compelling case for that young Russian defenseman he picked up, Yushkevich. That kid Warriner that we got in the Sundin trade is probably going to play. Zdenek Nedved looks like he'll make the roster. Mironov for Murphy! How did we pull that off??? Wow, this team is going for it!
1996: This is a contender for a bleak offseason. We thought we had a team built for the playoffs, we had brought in Muller, Gagner, Clark and Schneider. But we had a really disappointing first round. What's next? Are we in the running for Gretzky? Aw, shit, he went to the Rangers. Oh well, the gang's all here, still. Wait, what? Gartner gone for Nothing? Gagner gone for nothing? Gill for Jamie Baker? We've got those two european forwards Berezin and Modin coming in, but there's no doubt about it, this team has taken a step back.
1997: OK, we had an off year, but we got rid of Murphy and still have a good #1 in his prime to anchor the D. Clark had a good year, he's coming back. We got three really good assets for Gilmour, and all of them are going to play. That Mike Johnson kid who came in from college in March looks good. Berezin and Modin another year older. We signed Korolev and 2-time 38 goal scorer Derek King. Our top forward, defenseman and goalie are 26-28. Did we just successfully retool? Maybe! Too bad we couldn't successfully pry that Ohlund kid away from Vancouver, but wasn't that fun?
1998: Well, last year sucked, but there's lots to look forward to! Pat Quinn! And the top free agent jewel, Curtis Joseph. I'm not expecting much from Steve Thomas, but let's see how that goes. And apparently that Kaberle kid we got in the 9th round in 1996 might actually stick. And we have an excellent 2nd goalie now who can't possibly stay as a backup. Can't wait to see what we get for him in a trade.
1999: Wow, what a year that was. We got to the 3rd round and we're a really young team with lots of runway. That alone lends itself to tons of optimism. We get a full year of Bryan Berard this time. Picked up Hoglund as a free agent - maybe he'll mesh well with Sundin? And 70 point scorer Khristich! Sucks that we lost Sullivan but Khristich is better, I'm pretty sure.
2000: Another good year, but we ran into a New Jersey meat grinder. Our young, soft team needs some help. Enter Roberts, Corson, and Manson. Talk about a statement offseason. And then right before the season starts, we somehow turn freaking Karpovtsev into McCabe? You love to see it. Can't wait for the playoffs already.
2001: Well we sure gave New Jersey a run for their money this time. We just need a little something to get us over that hump. How about Alexander Mogilny? And to bolster the middle six, ex-Legion of Doomer Mikael Renberg, two time 88+ point scorer Robert Reichel, and once point-per-gamer now evolved into a checker Travis Green? Wow, can you say DEEP? This team is going for it! I love it.
2002: We got to the conference finals with a severely depleted roster. But still - Not a great offseason for optimism. Curtis Joseph left us and we replaced him with Belfour, who had a bad season and is even older than Cujo. We traded Yushkevich for Svehla! (see avatar). I love this guy! Always have. But basically we are running it back with a team that just ran out of gas. Hard to see it working out. Still, we'll be in the mix, like we always are. Let's see how it goes.
2003: So Quinn's going to just coach now, and we got a good, young bright up-and-comer in JFJ. He picked up Ken Klee, a solid veteran D, and Joe Nieuwendyk, a winner through and through. And that Stajan kid we drafted is closer to ready than we thought. Thank goodness Eddie the Eagle is not done yet. And we get a full season of Owen Nolan. Our window is still open, let's throw everything we have at this season before the lockout.
2004: lockout year. Can't get any more bleak when you have an old team and half of them are threats to retire. Have we seen the last of Nolan as a Leaf?
2005: TONS of reason for optimism. The dust from the CBA negotiations has barely settled, and we've just added Ontario boys in their primes - Lindros, O'Neill, Allison! Wow, are we ever going to be deep. And the rest of the gang is still here, other than 40 year old UFAs. Sucks we don't have Nolan, though. We really came out of this looking good. the realities of the new NHL have yet to hit us. Super optimistic.
2006: well if last season proved anything it's that this team is not good enough. we should really be looking to tear it down to the studs. Sundin, Tucker, McCabe, Kaberle could get us a lot back in trades. This Tavares kid is coming up in '09, this is good timing. Oh, we signed Kubina? well, he was a #1 D-man on a cup winner not too long ago. And Peca, well everyone loves Peca, right? and Hal Gill is solid too. I guess we didn't really miss the playoffs by all that much. Who knows what a change in the mix can do. And I really don't like that Rask for Raycroft deal, but we had to move on from Eddie, and besides, we still have Pogge. If you squint really hard, he's as good of a prospect as Rask.
2007: We were so close to the playoffs with a team built on Sundin and 28-31year olds. Raycroft wasn't terrible, I guess, and Maurice got a lot out of a lunchpail bottom-six. We really should be tearing it down, but since we aren't.... damn, we signed Jason Blake? That's a lot of money and term, but I guess he did just score 40 goals and maybe he's just what we need for Sundin. Still..... not feeling good about this core. If it wasn't good enough in 2006 or 2007, why would we think it's good enough in 2008 if you just add Blake to it? This Toskala guy better be good since we paid so much for him. I thought Raycroft was supposed to be the guy?
2008: after three years of just barely failing to make it, finally we can see some real changes. I like it. McCabe gone. Sundin gone. Tucker gone. Kaberle will be a good trade piece. So will Kubina. Jeff Finger? Well, Fletcher seems to be really high on him. This Luke Schenn seems like a winner. This is not a playoff team, and we didn't quite go down to the studs, but it's a start.
2009: Wow, Burke's first offseason sure was interesting. We paid a lot but getting Phil Kessel was a huge coup. We needed an actual needle-moving blue chipper on this team and we got him. a couple of solid free agent defensemen can only help. And I've been waiting for this Kulemin kid for years, let's finally see what we can do. And we got a new goalie out of Europe. I'm cautiously optimistic, but I can't help but feel like this team is trying to go young AND compete at the same time, and could fail at both goals.
2010: I think we are heading in the right direction. Versteeg is coming off a cup win. First full year with Phaneuf. First full year with Bozak. These guys can help. We might turn the corner.
2011: Everyone good on our team is 24-28. First full year with Lupul. This Jake Gardiner guy looks unreal in preseason, can't wait to see him more. I think Kadri makes the team permanently. Wow, did we seriously just get James Van Riemsdyk and all it cost us was Schenn? This kid Tyler Biggs we drafted is going to be the next Lucic!
2012: OK, we've got a young team that's making strides, and Kadri is going to make the team full time, for real this time! Jay McClement is a great under the radar signing, we need a guy like this to help team defense. We're going to turn the corner now.
2013: Well, I sure don't like how it ended, but we made the playoffs, and didn't even have to scratch and claw to get there. With such a young team led by studs Kessel and Phaneuf. Clarkson has scored 30 goals before and can really balance out the top-6, give it the look that it needs. He's a Toronto boy who bleeds blue and white. The term and money really scare me, but I really want to see this pan out. Also, Bernier could be our goalie of the future. Lots to like here.
2014: Really bad offseason. So much for our playoff team. Back in the dumpster. Clarkson was a dud. I hate to say it, but it's time to admit that this core isn't nearly good enough and what started as Burke's retool has failed. Tear it down to the studs please. What's that, you're going to run it back with the exact same core? GREAT.....
2015: YES! We traded Kessel. We are not trying to ice a competitive team this year. Look at all these ragtag misfit veterans we're signing. What is this, even? After a decade, is tank nation finally getting their wish? I love it, sign me up. Babcock is the biggest name in the business, and could be the guy to see us through a rebuild and come out the other side. And we just drafted Mitch Marner who might be the 3rd best player in the draft, at 5th overall. Things are really looking up.
2016: First overall pick! Auston Matthews! Now this is a guy you win with. I nearly hit my head on the ceiling when they won the lottery. We got a guy who is probably a legit #1 goalie. Babcock still here. And Nylander coming in along with Marner, wow, this is going to be a really interesting year!
2017: Back to the playoffs, and we're there to stay. This young team is only getting better and better. Window is officially open. Bring it on. that Marleau contract is scary, but he will help.
2018: OMG! Tavares! For nothing but the cap space. I love it. Bring on next season. With a one-two punch at center like this, how can we possibly lose? What a great first offseason for our young, bright, up-and-coming GM! We won't even miss Bozak and JVR.
2019: Kadri had to go, and I guess Kyle did the best he could with that one. Kerfoot might replace Kadri, and Barrie is at least a warm body. Spezza at leage minimum is good. This Mikheyev guy is promising. Ceci is a huge question mark but we got out from under Zaitsev and Hainsey. Gardiner and Marleau won't be missed. Thank goodness Marner is locked up now.
2020: As is becoming routine, we did not like how that season ended. But with the right tinkering around the edges and the core getting a year more mature, there's lots to like. Thornton coming in at league minimum. Brodie was a huge add. Good asset management with Johnsson and Kapanen.
2021: again, we didn't like the result. But this offseason was dubas going full Dubas. So many value signings and almost all of them paid off: Bunting, Ritchie, Kampf, Kase, Amadio. We have Campbell for another year at next to nothing and he's our guy, he's clearly proven he's better than Andersen, and this gives us room to have a better lineup.
2022: Definitely a "meh" offseason. Tinkering around the edges. Added checkers: Gaudette, ZAR, Jarnkrok, NAK. Big changes were in net. Goodbye Campbell, you couldn't get the job done and still became too expensive. Murray at retained salary is intriguing. Samsonov possibly a huge add. Good call letting Spezza go. Time for a new look bottom six. Let's run it back and hope we get the bounces this time.
2023: Getting really concerned here. We learned beyond a shadow of a doubt this spring, that this core just can't get it done in the playoffs. It's too much money to just four too-similar forwards. Something's gotta give. Dubas can figure it out. He admitted in his press conference that it's maybe the way to go. Oops, we fired him and hired the most vanilla GM we could get. And he wants to keep Keefe. And the core four. And is so attached to Kampf that he had to give him 9.6M over 4 years before free agency opened. And thinks Ryan Reaves is the answer to our toughness woes. And Nylander's NMC kicks in. And I'm like the only person in all of Leafs nation who believes trading Tavares is possible if you just make him uncomfortable. And Matthews is a UFA in one year and I can't decide if it's worse to lose him for nothing, or pay him $15M for 8 more years in which he'll probably score about 14 playoff goals and win one round in one of those 8 years. Yes, this is bleak. We have a very talented team in its prime with a wide open window and we are completely unwilling to make the big, bold moves necessary to take the next step. We stubbornly believe we already have everything we need. It's disgusting.
So in conclusion, I haven't been this disheartened by a Leafs offseason in my life, but 1996, 2007 and 2014 came really close.
Sorry, I didn't realize they had both. All good 
