This is all actually fairly straightforward if a little weird under boilerplate copyright law.
First, lacking model releases of his own, Jackson cannot use the photos for commercial purposes. He could use them as part of a portfolio but as soon as he puts one on a billboard or in an ad, he needs permission from the individuals who are identifiable in the image, which he doesn't have.
Second, in the absence of a contract Jackson owns the images, full stop. Nobody can put them on a billboard without his permission. He gave permission to put them on Facebook, but the going rate for use on billboards and in ads is much higher. $100K is not unreasonable for the level of use that has been demonstrated.
Third, Color Run almost certainly has a model release embedded in the paperwork the runners sign to enter the race, so they have the right on that count to use the pictures. They would be OK if they compensated Jackson, but they are not OK if they do not compensate Jackson. This is the ONLY way it is OK to put those pictures on billboards -- Jackson has to give permission to do so, for which he deserves much more compensation than he would get for use on Facebook, and Color Run has to do the publishing because they have the model releases.
The Color Run people are way out of line here and probably indulging in a snit because their authoritah was disrespected. But they are very clearly in the wrong.
As for trademark, that's completely irrelevant, since Jackson has no right to publish the pictures commercially without the model releases that Color Run has. However, Jackson DOES have certain Fair Use rights, such as releasing a few examples in the course of presenting his side of this story, as long as there is no danger of the images being misinterpreted as a commercial representation by Color Run themselves and as long as they serve certain alternate purposes, for which "news" qualifies.