It's interesting that a lot of the elite players best RS and PO are in different years.
Duncan Keith won the Norris in 2009-10 and looked every bit the best defenseman in the world. Yet, it's his Conn Smythe in 2015 that is his best playoff performance.
Crosby was utterly dominant in the 2008 playoffs and had a tremendous 2009 playoffs. Yet 2007-08 and 2008-09 are his two worst seasons between the ages of 19 and 26. He looked otherworldy in the 2010-11, 2011-12, and 2012-13 RS, yet got embarrassed in 2012 and 2013. Only to win back-to-back Smythes in 2016 and 2017 when he was no longer peak RS Crosby.
Ovechkin won the Smythe in 2018, yet I think we can all agree his peak play was 2007-08 -> 2009-10.
Patrick Kane had three dominant playoff runs in 2010, 2013, and 2015, but his RS dominance really took hold in 2016.
If I'm seeing things correctly, the only people to win the Conn Smythe and a major regular season award in the same season since 2000 are:
- Malkin in 2008-09 (Art Ross)
- Thomas in 2010-11 (Vezina)
- Lidstrom in 2001-02 (Norris)
- Brodeur almost did in 2002-03, as he was the favourite to win the Smythe on the Devils (Vezina)
The following people were on the 1st AS team when they won the Conn Smythe
- Vasilevskiy in 2020-21
- Crosby in 2015-16
- Thomas in 2010-11
- Malkin in 2008-09
- Niedermayer in 2006-07
- Lidstrom in 2001-02
You have to go back all the way to 1986-87 (Ron Hextall) for the next 1st AS and Conn Smythe in the same season.