Of all his brothers, it is Leonardo who spoils Michelangelo the most.
It seems like the most natural thing really, since Leo is the eldest and Mikey is the baby by designation. All the turtles treat Mikey as their littlest brother, and as much as Mikey complained that he is never taken seriously, he relished in being the baby of the family, taking advantage of Raphael's protectiveness, Donatello's patience and Leonardo's indulging.
Leo doesn't do it blatantly though. They are in small, subtle things, like talking Raph into participating in Mikey's skateboarding-in—the-lair stunt (and trying to wriggle them all out of punishment when Sensei caught them at it) and letting Dr. Prankenstein's water bomb hit his face. Leo is a trained ninja and he sees the prank probably a mile away. But Mikey's gleeful face is worth being pelted by twenty water bombs at the same time, and so he lets it hit him and pretends to be flabbergasted, hiding the smile that threatens to give it all away while Mikey crows triumphantly.
Oh but Leo would never admit to spoiling Mikey. He is the leader and thus he must be stern and strict and adhere to the rules. He does not have time for Mikey's scatterbrained antics, or so he said. But all those who know the turtle brothers could see that of all of Mikey's brothers, Leo denies Mikey his fun the least.
Casey sees it while they are at April's farmhouse. Leo's foot is still healing and he had been vetoed by Donnie, Raph and April to sit down and rest and not move so much. Casey had watched Leo fret over the uselessness of his legs, looking grumpily away when April or Donnie comes to offer him something to eat as a peace-offering. Moments later, Casey sees him sit in the patio, listening to Mikey ramble about banjo-playing spiders with the air and patience of an attentive older brother, all grumpiness wiped away from his face.
April sees it as she watches Mikey turn his huge beseeching eyes at his big brother, begging to tag along with Leo to Coney Island while looking for Karai. She hides a smile when Leo announced that Mikey will come with him for their three-way patrol, knowing full well that deep in his bones Leo is thinking that his youngest is going to be a pain with his uncontainable energy, his noises and short attention span while Leo is trying to save the girl-he-kinda-likes-but-is-technically-his-adopted-sister-and-now-a-mutated-snake-why-does-things-have-to-be-so-complicated in the middle of a Kraang-infested city. But still, Leo turns to the littlest turtle with a small smile as Mikey whoops with delight, his puppy eyes shining.
God, that puppy-dog look. Leo has never been able to resist that. Raph and Donnie have lived long enough with Mikey to somehow repel it when need be, but it seems that Leo never learned to. How many times have Mikey turn that look on Leo, and he just sighs and gives in to whatever mad scheme his littlest brother cooks up? Granted, most of Mikey's schemes turned out for the better – they would never had found out what a great ally Leatherhead is, for example - but the fact that Mikey could get his way around Leo by a simple look is something of an astonishment to their friends.
Raph and Donnie know, of course. He is, after all, the first to agree to Mikey's suggestion to LARP their way around "Mazes and Mutants" and create the maze around the sewers. As much as Leo tries to hide it, they could see it as plainly as the bands on their faces that Leo lets Mikey get his way. He might pretend to resist, but in the end Leo will always give in.
So when Leo splutters his indignation at Mikey's suggestion to bring Leatherhead back to the lair, Donnie silently counts the seconds it take for Leo to concede when Mikey pouts and widens his eyes at him. He doesn't go any further than nine.
And when Leo stubbornly refuses to collaborate with Spike, er, Slash and his team to defeat the Kraang, or at least hear him out, Raph turns to look at Mikey pointedly. He and his littlest brother have friends in the Mutanimals, and while Leo would switch on his bossiness if Raph had asked (without realizing it, Raph is sure), one puppy look from Mikey and Leo sighs and mumbles "fine".
All of Mikey's brothers look out for him in different ways. Raph defends, Donnie teaches.
Leo indulges Mikey the most.
Author's Note: Tweaked for grammar issues! I wrote this story because a lot of people seems to see Raph as Mikey's Big Big brother, but I do think Leo looks out for Mikey too, in his own way.
** I may consider making this into a Mikey four-shot, exploring his relationship with each of his brothers. I love all the turtles equally (although 2012-Donnie annoys me with his April-obsession) but Mikey has a special place in my heart