"In a gym on bleachers" is trouble. Gym lighting generally doesn't emit the full spectrum of color, so white balance is going to be tough. Additionally, it probably flickers with the AC current, so using a fast shutter speed is going to give erratic results.
How I would likely approach it:
Get as high as possible - e.g. on a ladder - and shoot down, so that the faces are somewhat closer to being in a plane that's parallel to the camera sensor. This allows you to keep everyone in focus using a somewhat wider aperture, and also reduces the chance that a person will be hidden behind the head of the person in front of them.
Set the camera to approximately the correct exposure for the gym lighting. Use a shutter speed of 1/60 - this is the absolute bottom edge of what I like for portraits, but I'd rather try to avoid capturing a partial cycle of the flickering gym lights. Set the aperture for the appropriate depth of field based on distance, focal length and crowd depth. Set the ISO for the correct exposure.
Clamp the camera (or tripod) to the ladder so I can take multiple shots, swapping faces in post if necessary.
Use bare flashes, each one a bit above and to each side of the camera, zoomed relatively wide. Set the power relatively low so that they supplement the ambient light for a little bit of fill, especially in the eyes; don't try to replace the ambient. Probably use a gel that's as close to the ambient color as possible.
On the umbrella: Maybe use an umbrella directly over the lens axis, maybe not. If I have plenty of power in the flashes then probably. If the umbrella is close enough to the subjects that its size makes a significant difference compared to bare flash, then it's also going to be close enough that the middle of the group will be way hotter than the outer edges of the group. To avoid objectionable light fall-off, you're gonna need to put your light source far away, which means more power, plus an additional couple of stops because the umbrella wastes/spills so much.
Additionally, I'd probably shoot a couple of test shots of a calibration tool such as the X-Rite Color Checker, which might help compensate for the ugly gym lighting. At an absolute minimum, a neutral gray reference is a must-have. White balance in gym lighting is gross.