Milloy was drafted by the Cleveland Indians as a pitching prospect out of high school and lettered three seasons in baseball at Washington.
In 1994, the Huskies advanced to the NCAA regional finals (Sweet 16), one round from the College World Series, but lost two straight in Wichita to Georgia Tech, led by future major leaguers Jason Varitek and Nomar Garciaparra.
[11] Milloy surpassed Terry Ray on the depth chart and earned the starting strong safety position after Week 7.
[10] On November 17, 1996, Milloy collected a season-high 12 combined tackles and made his first career interception during a 34–8 loss to the Denver Broncos in Week 12.
[10] Milloy made his first career interception off a pass by Broncos' quarterback John Elway, that was originally intended for running back Terrell Davis, and returned it for a 14-yard gain in the third quarter.
Milloy made his first career sack on Jets' backup quarterback Glenn Foley for a seven-yard loss in the third quarter.
[13] He finished his rookie season in 1996 with 82 combined tackles, two interceptions, two forced fumbles, and a sack in 16 games and ten starts.
On January 5, 1997, Milloy started in his first career playoff game and made five combined tackles and an interception as the Patriots defeated the Pittsburgh Steelers 28–3 in the AFC Divisional Round.
Milloy intercepted a pass by Steelers' quarterback Mike Tomczak, that was intended for wide receiver Andre Hastings, in the third quarter.
[10] On January 26, 1997, Milloy played in Super Bowl XXXI and recorded eight tackles during the Patriots' 35–21 loss to the Green Bay Packers.
On January 3, 1998, Milloy recorded ten combined tackles in the Patriots' 7–6 loss at the Pittsburgh Steelers in the AFC Divisional Round.
On September 20, 1998, Milloy recorded nine combined tackles and returned an interception for his first career touchdown during a 27–16 win against the Tennessee Oilers in Week 3.
Milloy intercepted a pass by Oilers' quarterback Steve McNair, that was intended for Yancy Thigpen, and returned it for a 30-yard touchdown to seal the Patriots' victory in the fourth quarter.
Head coach Pete Carroll named Milloy and Chris Carter the starting safeties in 1999, alongside cornerbacks Ty Law and Steve Israel.
[26] On January 27, 2000, the New England Patriots announced former New York Jets' defensive coordinator Bill Belichick as their new head coach.
[32] On November 19, 2000, Milloy collected a season-high 13 combined tackles, forced a fumble, and also made an interception during the Patriots' 16–13 win against the Cincinnati Bengals in Week 12.
Milloy recorded five combined tackles as the Patriots began their playoff run by defeating the Oakland Raiders 16–13 in the AFC Divisional Round.
On January 27, 2002, Milloy recorded three solo tackles, deflected a pass and made an interception during a 24–17 win at the Pittsburgh Steelers in the AFC Championship Game.
Milloy intercepted a pass by Steelers' quarterback Kordell Stewart, that was originally intended for wide receiver Plaxico Burress, and sealed the Patriots' victory in the fourth quarter.
[38] On February 3, 2002, Milloy started in Super Bowl XXXVI and recorded seven combined tackles and led the team with three pass deflections as the Patriots defeated the St. Louis Rams 20–17.
[45] He started all 16 games in 2003 NFL season and recorded 104 combined tackles (69 solo), eight pass deflections, three sacks, and two forced fumbles.
[37] On January 23, 2008, the Atlanta Falcons hired Jacksonville Jaguars' defensive coordinator Mike Smith as their new head coach.
[60] On December 14, 2008, Milloy collected a season-high 12 combined tackles (nine solo) during a 13–10 win against the Tampa Bay Buccaneers in Week 15.
[62] Head coach Jim L. Mora named Milloy the backup free safety, behind Jordan Babineaux, to start the regular season.
[63] On December 27, 2009, Milloy collected a season-high six combined tackles in the Seahawks' 48–10 loss at the Green Bay Packers in Week 16.
On October 17, 2010, Milloy recorded three solo tackles and a season-high two sacks during the Seahawks' 29–20 win at the Chicago Bears in Week 6.
[37] The Seattle Seahawks finished first in the NFC West with a 7–9 record and earned home-field advantage in the wild-card round of the playoffs.
[66] Despite interest in returning, Milloy was not re-signed by the Seahawks for the 2011 season, due to the emergence of 2010 draft picks Earl Thomas and Kam Chancellor.
Both his parents struggled with drug addiction during his childhood and his father was arrested for conspiracy to receive a controlled substance and was incarcerated for 2+1⁄2 years when Lawyer was 15.
Milloy moved in with his best friend during high school after a court hearing declared his mother an unfit parent and made Lawyer a ward of the state.