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Lola's Scheme
The question is, why would Lola advice the SHs to make Big Mom's acquaintance? In order to explore the motive, we need to understand who Big Mom is, and if it's such a good idea to interact with her.
She's not quite happy with the family she has, but desires a family tailor-made to suit her, therefore, they must be giants and she's on a mission to make this dream come true; we're slowly beginning to peek into what is surely...madness.
In advance, she organises parties, but, do they even want to attend this party? Doesn't look like they do, so they do attend; It's pleases her that they accept the invitations, but it's done out of fear, not love.
Both guests and family are in essence, hostages in an enactment of the perfect family that she so desires. Freedom revolves around herself, therefore, your freedom is her own freedom which is contrary to what freedom is; we see that she's the embodiment of grotesque solipsism (no pun intended) and absolute self-satisfaction.
Run-away Lola
According to Purin, we find out that Big Mom arranges her children's marriages in order to strengthen her crew. Her family are inherently bargaining chips. We find out based on this that Lola actually ran away from home as opposed to vacating carelessly.
No one runs away when there's nothing to run from, and it's deducible that Big Mom's tyrannical and overbearing nature led to Lola's longing to escape. It however begs the question, why did Lola send the SHs to this devil of a woman.
Lola's Observations
We're introduced to Lola at Thriller-bark which is run by Moriah. He was defeated by Luffy; his defeat so shocking because he's an individual who matched Kaido.
Why bring Moriah up? His ability in relation to Luffy is somewhat mitigated; Big Mom's ability seems to require fear to work. This is alluded to by M'ondor advising Moscato to remain calm, composed, fearless perhaps?.
Luffy is a completely fearless character; it's just in his nature to exude such disposition. We've see how this fearlessness, or strength of spirit has fared against some abstractly powered Devil fruit abilities. Moriah and Boa Hancock's power have been victim to his character, their power was somewhat mitigated due to his strong spirit.
Lola also recognised Luffy's willpower was great due to the number of shadows taken in...
They themselves, were only capable of taking 2-3 shadows, and estimated he'd only be able to take 20-30. He exceeded their estimation by absorbing 3x over.
Lola's Plan
We know she's acknowledged the strength of Luffy's spirit or at least, sees the potential in it. Big Mom's ability possibly will have a reduced potency against Luffy being that its efficacy is dependent on the target's fear..
Being that Moriah was defeated by Luffy which is a huge achievement, perhaps, she feels Luffy could cause another upset.
Bonus information: Just to add, Caesar was even working with Joker few years before the Marineford war. Big Mom was funding Caesar before he was under Joker which would tie in with the timing of Lola's captivity.
Based on all that's current known and bare in mind that Purin calls Lola her "dear" sister which suggest they were close, this may suggest that Lola wants Purin and her siblings to be free, so they can make their own decisions and live freely.
Like the image above, it says "we're counting on you, NIGHTMARE LUFFY", there's another NIGHTMARE, and it goes by the name...
GEAR 4TH
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