Erik,
Something bizarre is happening. Somehow, the servlet-api jar that is inside your webapp is being considered as being on the container classpath after a redeploy!
1st deploy here:
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///Volumes/CRBS/test-server-1/lib/apache-jstl/org.apache.taglibs.taglibs-standard-impl-1.2.1.jar in 128ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///Volumes/CRBS/test-server-1/lib/servlet-api-3.1.jar in 95ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/WEB-INF/classes/ in 49ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/WEB-INF/lib/commons-codec-1.6.jar in 125ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/WEB-INF/lib/gson-2.2.2.jar in 144ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/WEB-INF/lib/h2-1.4.188.jar in 333ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/WEB-INF/lib/hamcrest-core-1.3.jar in 78ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/WEB-INF/lib/javax.servlet-api-3.1.0.jar in 26ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/WEB-INF/lib/javax.ws.rs-api-2.0-m10.jar in 28ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/WEB-INF/lib/junit-4.12.jar in 167ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/WEB-INF/lib/olingo-odata2-api-2.0.4.jar in 151ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/WEB-INF/lib/olingo-odata2-core-2.0.4.jar in 181ms
2015-10-26 06:15:47.751:DBUG:oeja.AnnotationConfiguration:main: Scanned 2 container path jars, 9 WEB-INF/lib jars, 1 WEB-INF/classes dirs in 336ms for context o.e.j.w.WebAppContext@6d8a00e3{/JUnitRM,file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/,STARTING}{/JUnitRM.war}
then on the redeploy:
2015-10-26 06:16:21.745:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-1985591512874713986.dir/webapp/WEB-INF/lib/javax.servlet-api-3.1.0.jar in 0ms
2015-10-26 06:16:21.745:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///Volumes/CRBS/test-server-1/lib/apache-jstl/org.apache.taglibs.taglibs-standard-impl-1.2.1.jar in 64ms
2015-10-26 06:16:21.745:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///Volumes/CRBS/test-server-1/lib/servlet-api-3.1.jar in 48ms
2015-10-26 06:16:21.745:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-7607105486472461234.dir/webapp/WEB-INF/classes/ in 19ms
2015-10-26 06:16:21.745:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-7607105486472461234.dir/webapp/WEB-INF/lib/commons-codec-1.6.jar in 70ms
2015-10-26 06:16:21.745:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-7607105486472461234.dir/webapp/WEB-INF/lib/gson-2.2.2.jar in 70ms
2015-10-26 06:16:21.745:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-7607105486472461234.dir/webapp/WEB-INF/lib/h2-1.4.188.jar in 234ms
2015-10-26 06:16:21.745:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-7607105486472461234.dir/webapp/WEB-INF/lib/hamcrest-core-1.3.jar in 31ms
2015-10-26 06:16:21.745:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-7607105486472461234.dir/webapp/WEB-INF/lib/javax.servlet-api-3.1.0.jar in 20ms
2015-10-26 06:16:21.745:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-7607105486472461234.dir/webapp/WEB-INF/lib/javax.ws.rs-api-2.0-m10.jar in 19ms
2015-10-26 06:16:21.746:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-7607105486472461234.dir/webapp/WEB-INF/lib/junit-4.12.jar in 136ms
2015-10-26 06:16:21.746:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-7607105486472461234.dir/webapp/WEB-INF/lib/olingo-odata2-api-2.0.4.jar in 119ms
2015-10-26 06:16:21.746:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-7607105486472461234.dir/webapp/WEB-INF/lib/olingo-odata2-core-2.0.4.jar in 140ms
2015-10-26 06:16:21.746:DBUG:oeja.AnnotationConfiguration:Scanner-0: Scanned 3 container path jars, 9 WEB-INF/lib jars, 1 WEB-INF/classes dirs in 236ms for context o.e.j.w.WebAppContext@72ffc175{/JUnitRM,file:///private/var/folders/sj/jyk9h8792tzfgdy2by2p72yr0000gn/T/jetty-0.0.0.0-8080-JUnitRM.war-_JUnitRM-any-7607105486472461234.dir/webapp/,STARTING}{/JUnitRM.war}