Why didn't Littlefinger try to have Ned killed before the books started?

[Angel Eyes]

If Catelyn was the prize (for lack of better term) that Littlefinger wanted, why didn't he try to bump off Ned at any point before the books began? A catspaw? A crossbowman with a clean line of sight up to and including one mile from Winterfell (Saving Private Ryan reference)? Bribe a Northern lord (say Roose Bolton) to have Ned poisoned?

[Finley McLeod]

I would risk a guess and say he reasoned it out properly.  The death of Ned is not going to drive Cat in his arms.  Petyr Baelish knows Cat doesn't lust for him.  It would take a chain of events that would put Cat in desperation before she would turn to him for physical comfort.  Like the destruction of Stark and Tully.  Cat will have no money and nowhere to go.  In he comes from the left side of the stage to rescue her from poverty. 

[nyser1]

26 minutes ago, Finley McLeod said:

I would risk a guess and say he reasoned it out properly.  The death of Ned is not going to drive Cat in his arms.  Petyr Baelish knows Cat doesn't lust for him.  It would take a chain of events that would put Cat in desperation before she would turn to him for physical comfort.  Like the destruction of Stark and Tully.  Cat will have no money and nowhere to go.  In he comes from the left side of the stage to rescue her from poverty. 

This. Also, who says he would be able to pull it off?

[James Steller]

20 hours ago, Angel Eyes said:

If Catelyn was the prize (for lack of better term) that Littlefinger wanted, why didn't he try to bump off Ned at any point before the books began? A catspaw? A crossbowman with a clean line of sight up to and including one mile from Winterfell (Saving Private Ryan reference)? Bribe a Northern lord (say Roose Bolton) to have Ned poisoned?

Littlefinger is meant to be a dangerous man, highly intelligent and amoral. The one flaw he has is his obsession with Catelyn Stark. He will do the illogical, recorrect his plans, all for Catelyn or her daughter, Sansa. It’s going to be his undoing.

[Tywin Manderly]

On 10/13/2019 at 8:44 PM, Angel Eyes said:

If Catelyn was the prize (for lack of better term) that Littlefinger wanted, why didn't he try to bump off Ned at any point before the books began? A catspaw? A crossbowman with a clean line of sight up to and including one mile from Winterfell (Saving Private Ryan reference)? Bribe a Northern lord (say Roose Bolton) to have Ned poisoned?

Before the books commenced Littlefinger was way beneath the birth and station of the Lady Catelyn Tully Stark, so even if he would pull off the tremendously difficult feat of killing Ned on his home turf he would never be considered as a prospective spouse for her, if she were to remarry at all. 

Littlefinger could marry Lysa in ASoS only because:

1. Lysa is an infatuated idiot;
2. it was in the interest of the powers-that-be, Tywin Lannister & Co, to let him marry Lysa because they wanted to get the Vale in their fold so they granted him what was societally necessary to so: the Lordship of Harrenhal and the Lord Paramountship of the Trident.

[Lost Melnibonean]

On 10/13/2019 at 2:44 PM, Angel Eyes said:

If Catelyn was the prize (for lack of better term) that Littlefinger wanted, why didn't he try to bump off Ned at any point before the books began? A catspaw? A crossbowman with a clean line of sight up to and including one mile from Winterfell (Saving Private Ryan reference)? Bribe a Northern lord (say Roose Bolton) to have Ned poisoned?

He was playing a long game and relishing it...

https://asoiaf.westeros.org/index.php?/topic/89914-littlefinger-hired-a-faceless-man-to-kill-ned/

[Dreadscythe95]

Littlefinger didn't want Catelyn, he wanted chaos and opportunities. He doesn't even have a complete plan, he has a concept of how he wants to make his moves when the opportunities arrive. So he tries to create the opportunities. The big idea was to start a conflict between Great Houses and he did by murdering Jon Arryn and blaming The Lannisters.

[Jeeves]

He had no reason to.  Catelyn is what, pushing 35 now.  She could choose to stay unmarried. 

[The hairy bear]

Littlelfinger was obsessively infatuated with Catelyn in his youth, but I think it would be incorrect to assume that it was the same later in his life. It seems clear that his passions moved on onto to the nobler pursuits of amassing wealth and power. If he had still been in love with her, he would have tried  to see her. It would have been easy for him to make some excuse for a visit to Winterfell (he could have accompanied Robert in his trip North).

 

[Lord Varys]

Unfortunately, we don't need the contents of the letter he sent Cat which she burned unread. I could see him promising her that they would be together one day, after he had made himself worthy of her (i.e. by climbing to the top of the food chain).

Chances are not that bad that he had Lysa write the letter so he could draw Ned and Cat down to court (he would have expected that Cat, wanting to be with him considering he she loves him in his mind, would accompany Ned) where they could continue as they had left off. Plan B was to marry Lysa to continue his rise to power, plan A was to use Ned as long as he could, and then pull a Lysa & Petyr on Ned with Cat's help.

You have to keep in mind that part of the Sansa obsession honestly is the 'Sansa the daughter he and Cat never had' fantasy - something that would have been even more real if Littlefinger had become Cat's second husband and the stepfather of her children.

There wouldn't have been any Sansa nonsense fantasy, one assumes, if Cat had 'renewed' her affair with Littlefinger early on in AGoT.

In that sense targeting Ned could only come rather late in the plan for advancement - and wouldn't have been that great a priority anyway, since Littlefinger actually never had any issues with Ned.