I've been sitting on this one for a bit, some of you have heard it in parts, but I've finally consolidated my thoughts into one little thread: The significance of the Army Men in #TedLasso, and who Ted gave them to. 
Rebecca: The figure he gives her is in a defensive pose - and he places it on the desk, purposely between her and the door - it's protective and he says as much. He wants her to feel safe. It also speaks to Ted's instinctual reaction to Rebecca, and his want to support her.
...Also it touches on their soulmates/guardian angels thread, that is just in the early stages at this point. With Rebecca & the Army Man, Ted's motivations are a lot more overt, but the underlying theme is subtle and gives a lovely insight into what's to come for them as a unit.
Sam: Probably the least significant pairing of Army Man to character. The importance here is not the figure he gave Sam, but the fact that he gave it back.
The honest exchange here is what matters and it gives a nice insight into their principals and how Sam and Ted respect each other's cultural differences, but also see a lot of similarities in each other, as well. (the reference to Sam's Dad pinching his earlobes)
Ted: Not a gift, but when he goes to sign his divorce papers, there's an Army Man laying down on the desktop. As he makes the decision to finally sign the papers he's been procrastinating about, he stands it upright.
The figure is lobbing a grenade. Which could be a metaphor for the decision he's made - and he's tossing it out into the unknown. Also, when you hold onto a live grenade too long, you can get severely hurt which is another metaphor for their marriage needing to come to it's end.
Jamie: The figure he gives Jamie doesn't have a weapon, he has binoculars. The metaphor being that Ted can SEE Jamie - probably for the first time in his life, someone is telling Jamie he can see his potential.
He can see not only what he's already capable of as a player, but his potential as a man and it's Jamie's first real conscious step towards choosing to be a better person.
Sharon: The figure he gives Sharon has a backpack - a metaphor for the burdens she carries on behalf of everyone else, on his behalf - and the fact we only saw hinted at the baggage she carries for herself.
He's also got a radio - As their therapist, Sharon is the listener. She listens to their fears, anxieties and issues with a compassionate ear.
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