I should add that the contemporary evidence you found of Day assigning a shadow to Maurice Richard doesn't seem to jive with the idea of playing a trap. Shadowing and trapping have little to do with one another, and those weren't actually terribly deep Montreal teams. Just shadowing the Rocket would make more sense.
The trap and shadowing are compatable; Jacques Lemaire had Claude Lemieux shadow Cam Neely in the first round of the 1995 playoffs to great success.
I don't think I have fully explained how I see the Ottawa team working. I'll take a post to do so before getting to the specific matchup with Chicago.
As explained before, the basic concept is built around playmaking centres, two-way wingers who can skate and score, and defenders who can provide a threat from the blueline. Ottawa's centres will have a lot of options in distributing the puck on the attack. And of course Patrick Roy gives us an advantage in any playoff series.
On the first line, Toe Blake and Elmer Lach were great players before Maurice Richard ever joined them. Blake, of course, had a scoring title and a Hart trophy in 1938-39, when he dragged his undermanned team to the playoffs with a strong finish to the season. Lach and Blake teamed up in 1942-43, and their RW Joe Benoit (who?) finished second in goals scored that year. Both were skilled scorers and passers as well as hard-working two-way players. Marian Gaborik brings speed and finishing ability to the line. He has been among the best EV scorers in the league for a decade now and he'll get a lot of opportunities from his linemates. If Gaborik isn't getting the job done any of Ottawa's four RWers is capable of taking his place.
The Andreychuk-Cowley-Hossa line follows the classic slot man - puck man - boards man formula. Few if any were better in the slot than Dave Andreychuk, a huge, strong player who could take a ton of abuse and put the puck in the net with his soft hands. Bill Cowley was the outstanding offensive player of his generation and an all-time great when it comes to puck skill and playmaking abilities. And Marian Hossa combines ATD top-6 skill level with a bottom-6 work ethic and excellent board play and checking ability.
Sutter-Watson-Taylor may not win every shift but they'll never get outworked. Fiery Phil Watson leads the line as an outstanding skater, checker, and a skilled playmaker who played with an edge. Both Sutter and Watson were extremely hard-working players who scored in first line roles during their NHL careers but will step down a bit and play more of a checking role here.
On the fourth line, Patrice Bergeron has been an excellent two-way centre for almost a decade. In the past two seasons he has been the best defensive centre in the league and in my opinion he is the best defensive centre I have seen in the past decade*. Georges Mantha and Ken Wharram are a pair of speedy wingers who can work hard, check, and counterattack. Wharram was more of a scorer in his NHL career than Mantha, who spent most of his career in a checking role but scored when asked to do so.
On the blueline, Ottawa has spread out their top defenders to create two very strong pairings. On the top pairing, MacInnis is the better offensive player and will bring a unique offensive weapon to the ice. Both were known as strong defensive players, excellent positionally and with their sticks, with good size.
Doug Wilson and Art Ross on the second pairing were both fine two-way defenders. Ross was arguably the best defender in the world for some time after Hod Stuart died, and was both a skilled puck-rusher and a defensive stalwart at the point position. Wilson was also an excellent skater and skilled player, both offensively and defensively.
Stackhouse-Regehr will play a more limited role. Size and strength defensively. Stackhouse moves the puck and Regehr knocks unsuspecting forwards into next week.
In goal, Patrick Roy is arguably the best playoff performer in hockey history. He was a very skilled goaltender and an incredible competitor. In real life he never won fewer than 3 games in a playoff run. For whatever reason he has not matched that success to date in the ATD, but I am confident that this is the team to break that trend,
Ken Hitchcock is among the most accomplished coaches of the post-dynasty NHL, with a consistent track record of success wherever he goes, especially with the unique and memorable Dallas Stars team of the late 1990s.
On special teams, Ottawa's power play should be formidable with MacInnis and Wilson spreading out and bombing away from the points, Andreychuk parked in front of the net, and Cowley setting everything up. The penalty kill will be more of a team effort, with Patrick Roy as the last line of defence.
Ottawa also has terrific leadership. Starting with the forwards, Toe Blake was a great captain for Montreal, a player who his contemporaries said had an unmatched will to win. Dave Andreychuk made his mark in history by his leadership in Tampa Bay, establishing a culture that allowed them to win the Cup. Brian Sutter was a captain at age 23, spent 9 years as captain, and transitioned directly into the head coaching position at age. Watson, Taylor, and Bergeron were also hard-working team leaders.
On the blueline, MacInnis wore a letter for much of his career and was immensely respected by teammates for his quiet leadership. Art Ross was an on and off ice leader among his peers for most of his career. Lowe wore a letter for a dynasty, and Wilson also wore a letter for many years.
Interesting note about these Senators - many went on to success in hockey after their playing careers. Toe Blake became arguably the greatest coach in hockey history. On the third line, Brian Sutter and Phil Watson both had extensive careers as coaches, and Dave Taylor has done the same in the front office. In fact, Sutter went directly from the ice to a head coaching role. On the blueline, Kevin Lowe and Doug Wilson have both been longtime GMs, and Art Ross was a great and innovative coach for many years. While their post-playing career is separate, it's an indicator of their intelligence, work ethic, and leadership as players.