Before enrolling at Western Oregon University, Boss played varsity level football at Philomath High School,[1] becoming a stand-out tight end.

Then as a senior, his team won the state title game (2002), picking up honorable mention All-State and All-League first-team accolades as well.

As a tight end, he started all team games, registering 39 receptions for 506 yards (13.0 average) and five touchdowns on the field earning first-team All-GNAC and All-Region accolades.

[2] He also returned one punt for 13 yards, recorded four solo tackles and recovered one fumble, picking up first-team All-American, All-Region and All-GNAC honors, all in the eleven games he started for the Wolves.

On the basketball court, Boss averaged 3.5 ppg (points per game), pulled down 90 rebounds and led the Wolves with seventeen blocked shots.

[2] Boss graduated as a physical education major, with a minor in business, earning Academic All-District VIII honors with a 3.2 grade point average.

Boss went on to gain two more receptions in the Divisional and Conference rounds of the playoffs against the Dallas Cowboys and the Green Bay Packers respectively.

Boss and his team then went on to Super Bowl XLII in Glendale, Arizona, where they were matched up against the previously undefeated New England Patriots.

Entering Giants mini-camp, Boss arrived weighing 272 pounds,[5] a significant increase in weight compared to the previous year.