Revisions to the playoff seeding system in 1993-94 awarded division winners with the top spots in each conference. In the 15 seasons since, a division champ has made the Stanley Cup Finals every year, winning it 12 of the 15 times.
Year: Stanley Cup Finalists
2009: (4) PIT over (2) DET
2008: (1) DET over (2) PIT
2007: (2) ANA over (4) OTT
2006: (2) CAR over (8) EDM
2004: (1) TBL over (6) CGY
2003: (2) NJD over (7) ANA
2002: (1) DET over (3) CAR
2001: (1) COL over (1) NJD
2000: (4) NJD over (2) DAL
1999: (1) DAL over (7) BUF
1998: (2) DET over (4) WAS
1997: (3) DET over (2) PHI
1996: (2) COL over (4) FLA
1995: (5) NJD over (1) DET
1994: (1) NYR over (7) VAN
The only non-division winners to hoist the hardware since the new seeding scenario are New Jersey (5th seed in 1995, 4th seed in 2000) and Pittsburgh (4th seed in 2009). Interestingly, both failed to win as division champions (NJD 2001, PIT 2008).
The Presidents' Trophy winner has made it to the Finals six times in this span (NYR 1994, DET 1995, DAL 1999, COL 2001, DET 2002, DET 2008), claiming the Cup in each appearance. Amazingly, only once have the top seeded teams in each conference met in the Finals (2001). At the other end of the spectrum, Cinderellas' seeded 6th or worse have found themselves there five times (VAN 1994, BUF 1999, ANA 2003, CGY 2004, EDM 2006). None have won.
In short, unless you're the Devils or Penguins, your best bet to sip from Lord Stanley's mug begins with clinching your division. That way, at least, you have history on your side.