On paper it looks awesome, but that '99 team was starting to show some warts:
-Lots of guys banged up and dealing with injuries after 4 consecutive deep playoff runs, and they no longer had the depth they had the previous 2 seasons. And despite what Ken Holland thought, they really didn't have any young guys ready to make any sort of impact at the NHL level...
-Beyond Lidstrom and Murphy, their defense was a mess... Holland let Rouse, Fetisov and Mironov walk while making what he thought was a big splash in signing Uwe Krupp and promoting prospect Yan Golubovksy to the NHL roster. The Krupp signing was a disaster, Macoun played like he was 5 years older without Bob Rouse..., Aaron Ward, Anders Eriksson and Yan Golubovksy were pretty much stuck in Bowman's doghouse, with Ward requesting a trade out of town... To fill some of the gaps, Bowman moved winger Mathieu Dandenault to Defense, which cut into their forward depth, and they would eventually claim Todd Gill off of waivers, only to eventually be lost longterm to injury as well.
The trade deadline acquisitions were more about filling holes that going all in on a 3-peat.
For context, look at the Wings line-up in their last game before the deadline:
Get the latest box score updates on the Detroit Red Wings vs. Philadelphia Flyers game played on March 21, 1999 on Hockey-Reference.com
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Kocur, Larionov and McCarty were injured, while Kirk Maltby was suspended for a slash that broke Valeri Kamensky's wrist (which would haunt the Wings later on). Gilchrist was playing in only his 2nd game of the season, but would re-aggravate his injury and miss the next game, which would've meant they would have to call up another forward to keep Klima and LaPlante company on the bench for 58 minutes had they not acquired Clark.
And this came after the Avs had added a couple of good rookies in Hejduk and Drury and then brought in Fleury and Dale Hunter. Dallas had added Hull and while they didn't get any big names, they had also added some depth to their roster before the deadline.
Then once all was said and done, none of those deadline acquisitions really moved the needle for the Red Wings... Samuelsson was hurt when they acquired him and never really seemed to get going before he got hurt again during the 2nd round... Clark moved like each of his skates weighed 150lbs... The hockey media's over rating of Ranford had finally ended in Tampa and he had that epic meltdown against the Avs in games 3 and 4, and even Chelios had the Detroit media wondering if he was the right move after he went -8 in 6 games against the Avalanche.
Based on all that, I don't see the '99 Wings getting past the Stars, but they likely would've beat the Sabres.