Kawakami interned at the
Philadelphia Daily News, and became their
beat writer for the
Philadelphia Eagles in the late 1980s. He joined the
Los Angeles Times in 1990 and covered the
Los Angeles Rams before moving to
boxing in 1993. While continuing to cover boxing, he began covering
UCLA Bruins men's basketball in their national title season in 1994–95. He became the beat writer for the
Los Angeles Lakers in 1998–99, covering the
basketball team through the
Shaquille O'Neal–
Kobe Bryant era. Kawakami started his "Talking Points" blog in 2006. He began a podcast series, “The TK Show”, in 2015, Kawakami left
The Mercury in July 2017 to become the editor-in-chief of the
San Francisco Bay Area edition of
The Athletic. He joined
The San Francisco Standard on September 13, 2024, together with fellow
Athletic journalist
David Lombardi. Kawakami said his departure stemmed from a desire to prioritize local sports coverage, a focus he felt was shifting at
The Athletic in favor of a broader, national perspective.
SFGate wrote that Bay Area media circles generally considered him to be "credible, fair, and tenacious". ==References==