In a very large skillet heat 1 tablespoon of the olive oil over medium high heat. Season the chicken on both sides with salt and pepper. Sear the chicken for about 3 minutes on each side or until browned and just barely pink in the center. Do this in batches if needed, and remove the chicken to a plate and set aside.
Return the skillet to medium heat, add the remaining tablespoon of olive oil, and when it’s hot add the shallots, and sauté for 2 minutes until they start to become tender. Add the orzo and stir for another minute until the orzo is nicely coated with the oil and shallots. Add the chicken broth and bring to a simmer, scraping up any browned bits from the bottom. Stir in the half-and half and return to a simmer. Cover the pan, lower the heat and simmer gently for 8 or so minutes, stirring occasionally, until the orzo is almost - but not quite - tender and much of the liquid has been absorbed - it should still be very runny though, with actual liquid still left in the pan.
Sprinkle in the Gouda and Butterkase cheeses in batches, stirring after each addition until the cheese is all melted. Stir in the oregano and baby kale, then tuck the browned chicken into the orzo mixture, and drizzle over any juices that have accumulated from the chicken. Cover the pan and simmer for another 3 minutes or so, until the chicken is cooked and the orzo is tender. The orzo will still be saucy and loose.
Serve the chicken and orzo hot from the pan. It's going to thicken and firm up as it cools, so don't be worried if it seems saucy at first.
This post has been sponsored by Roth cheese. All the opinions expressed are my very own.