I would say it sounds like your real boss needs to more clearly define job roles, but it sounds like you should talk to your boss and tell him that you will likely be the primary developer and that you'd like to discuss the non-portlet option more. I think it's important to not make it look like you're just trying to overrule the other guy -- rather you want to open the discussion again. That will show them that you actually care about the decision.

[oracle-rant]
As far as using Oracle stuff vs JSP -- I haven't used portlets, all I can say is that Oracle may have the fastest database in the world, but they suck at writing applications for developers. I get so angry every time I work with Oracle and get a -234091 error with a cryptic error message (i mean really, what year is this? you can't tell me the name of the column that had a problem?). With JSP/Servlet/J2EE, you have many options of deployment platforms, you have many open source options, you have a ton of community tools and IDE integration tools for development, and you don't get vendor lockin like with everything Oracle touches. If you ever decided that perhaps you didn't need or want to be paying $30k a year in Oracle licensing, if you've probably written your application with j2ee, you can switch out your database. If you ever need to deploy your app on someone else's system, you can cut the deployment cost WAY down (you can deploy on Apache + Tomcat + PostgresSQL, or maybe they want to use SQLServer).

In general, the more standard something is, the better, in my mind. If it says Oracle in the title, you can probably count on it screwing you later on.
[/oracle-rant]

That being said, we use Oracle here for our primary database (like I said, it's fast), but we also deploy on pgsql as on option.

ms