In 2002, Taylor returned to the U.S. to play for the New England Revolution in Major League Soccer, quickly proving himself to be one of the best players in the league. In his first season, he scored 23 goals and scored his first professional hat trick.

Unfortunately, Taylor suffered a neck injury and a concussion during a 2008 game that proved to be a career ending injury. The soccer player announced his retirement from the MLS in 2010. Due to his multiple concussions throughout his career, Taylor has agreed to donate his brain to science after death to help determine whether multiple concussions cause permanent harm to the brain.

Taylor's retirement didn't end his love of soccer. The soccer player joined ESPN in November 2011 as a soccer analyst. He was the lead color commentator for the MLS until January 2023. During his time there, Taylor hosted a weekly recap show, called several European Championships, and was the USMNT lead color commentator in the World Cup in Brazil.

After leaving ESPN in early 2023, Taylor joined Apple's MLS coverage and started his own podcast, Offside With Taylor Twellman.

In 2003, while Taylor was still playing in the MLS, he married his high school sweetheart Lindsey in a ceremony in St. Louis. But, after just four years together, they filed for divorce. At the time, Sports Illustrated asked the athlete if he would be up for a team transfer, to which Taylor responded: "I went through a horrible divorce and that took its toll. I thought I was strong enough to handle and I wasn't. The last thing on my mind right now is a transfer. I just want to have a beer after the game tonight."

Following his divorce, Taylor has kept his relationship status private.

While he doesn't share much about his love life, Taylor is a proud girl dad. He has two daughters, Rose and Lucy. During a LPGA event in 2023, Taylor shared that his daughters look up to several female professional athletes. 

"I've got two lovely daughters," he told ASAP Sports. "Rose is five and a half and Lucy is two and a half, and so if my daughters are acting the way Céline [Boutier] and Mo [Martin] are the last two days, then I did a good job raising my daughters."