They really don't, though. Statistically, it's more rare for teams in certain circumstances to reach the Finals than it is for other teams, and especially to win.
Here's an example, with Columbus' run specifically in mind, where Kekalainen went all-in on the roster. This was the argument to begin with. They had never even won a playoff series in their existence, but according to you and Leap, they had an equal chance at the Cup with all the teams that made the playoffs that year.
Let's look at teams that, prior to their championship run, had never won a single playoff series in their franchise’s history.
1. 1974 – Philadelphia Flyers
2. 1996 – Colorado Avalanche
That's it, that's the list.
Now, let's expand that a bit further to open it up a little bit more. Here's a list of finalists that, in the two or more seasons prior to their finals appearance, did not make it past the first round of the playoffs -- either losing in the first round or missing the playoffs entirely. This is since the modern era, 1970s and onward.
1. 1991 – Minnesota North Stars (Lost in Final)
1989: Missed playoffs
1990: Missed playoffs
1991: Reached Final
2. 1996 – Florida Panthers (Lost in Final)
1994 & 1995: Missed playoffs (expansion team)
1996: Reached Final in 3rd season
3. 2002 – Carolina Hurricanes (Lost in Final)
2000: Missed playoffs
2001: Missed playoffs
2002: Reached Final
4. 2006 – Edmonton Oilers (Lost in Final)
2002: Lost in 1st round
2003: Missed playoffs
2004: Missed playoffs
2005: Season canceled
2006: Reached Final
5. 2010 – Philadelphia Flyers (Lost in Final)
2008: Lost in 1st round
2009: Lost in 1st round
2010: Reached Final
6. 2012 – Los Angeles Kings (Won the Cup)
2010: Lost in 1st round
2011: Lost in 1st round
2012: Won Cup
So since the 1970s, this has only happened SIX times, and only one of those teams won the Cup.
So despite what you and Leap claim, there are statistical weights to each team, each year, based on previous accomplishments that can define their probability of success that can be used to determine their reasonable chances at winning the Cup or competing for it. Yes, there are always exceptions, like the above teams, but clearly in 2019 the Columbus Blue Jackets, based on precedent, wasn't likely to end up in the Finals competing for the Cup, let alone winning it.