Leave the bald cypress in a draining pot over the winter. Flood your bald cypress from March to October. I'm getting ready to punch holes in all of my non-draining pots.
In the Spring, I'll be putting my draining pots into larger non-draining ones. I keep small bottles of insecticidal oil on all my benches. A few drops keeps the mosquito population down. I have to use a pet-safe oil because my dogs like bald cypress tea.
That pot looks to be about 10-inches tall. It's time to decide just what do you want to do? I have a few trees with trunks like that, so here's what I'm doing in the Spring:
Cut the roots so that all of my trees will fit inside of a 7-inch bus tub. I want the soil level to be about 1-inch below the rim of the pot. I trim the top-most roots down to a level where I have the beginnings of a nice radial flare. I want that radial flare to be submerged.
I do have access to 9-inch tubs as well. I'll cut the roots so that they fit inside of a 7-inch tub, but I plant them in the 9-inch tubs for added depth of water.
If I've punched holes in the tubs for drainage, I put the tubs into much larger black plastic tubs I get from one of the big-box home improvement stores.
I do ZERO WORK on the trees, just flood and drain, until I get a nice response from the base. The first one I had that gave me a crazy big base went to Zack Smith. I have others that are responding very well.
BUT NONE OF THIS MEANS ANYTHING WITHOUT VISION. You need to come up with a vision for your tree. My vision involves fat bases that taper very quickly and become tall lithe trees.
Good luck!