It seems to be the consensus that the Senators are the worst team in the league and have been for nearly a couple years now. They might still be in the conversation for a couple more years, but who do you think will succeed them as the worst team in the league?
Senators definitely for the next couple years. But there are a few strong teams that might drop off sooner rather than later:
Pens: A lot of their core at the end of their current contracts are going to be on the old side (Malkin will be 35 in his last year 21/22, Crosby will be 37 at the end of his contract in 24/25, will be 34 in Malkin's last year, Letang will be 34 in his last year 21/22, Jack Johnson will be 36 in 22/23). That team's best players are starting to get up there. Not saying they won't be good, short of injury Crosby is still going to be Crosby, he just won't be 100 point Crosby. Hell, by 35 he might only be a 65-70 point player (not bad by any means, but not a guy who can drag his team to the playoffs). They've also traded a lot of high picks (1 first round pick in the last 5 years, 3 third round picks, though they did keep a lot of their 2nd rounds). Admittedly, if they keep their firsts and land a couple home runs on a few other picks in the next few years, they might avoid bottom feeder status, but as it stands, their core is definitely aging out, and lacking the talent to really replace it (currently).
Chicago: Basically the same situation as the Pens. Their core is going to age out, and they seemingly lack the talent to replace it (currently). Kane and Toews both have their final seasons on their current contracts in 22/23 (age 33 and 34 respectively), Seabrook will be 38 in his final year (23/24) Keith will be 39 (22/23), Crawford is 34 this year (and it's his last year of his contract).
In both those cases, these are teams who have won a lot recently (3 cups in 5 years for Chicago, and 3 cups in 9 years including back-to-back championships for Pittsburgh). They achieved the pinnacle, and are paying for it now.
San Jose: Again, I feel they'll still be good for a few more years (give or take 3-4 years, depending on how their D ages). But their team is definitely up there in age. Burns is 34 (his contract takes him to 39), Vlasic is 32 (his contract takes him to 38 I believe), Karlsson is likely going to fall off in his 30's (his biggest asset is his speed, and that's not likely to last through his contract which takes him to 36. I figure he still has 4 more good years or so barring injury), Couture is 30 this year, (his contract takes him to 37). Marleau and Thornton are both 30 this year. The upside is, I feel they have at least a bit of replacement talent already in their pool to help replace as these players age out, but the next few years of drafting could make or break them.
Again though, all it's going to take is one or two good trades, or a couple good drafts and this doesn't happen to any of these teams. I'd also say the wild, but I really feel they never totally bottom out, they remain just... average, somehow.