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On March 6, 2020, Kempin joined USL Championship expansion side San Diego Loyal SC on loan for the 2020 season.

After not making a single appearance through the first two months of the 2019 season, Kempin was sent on loan to USL Championship club Hartford Athletic on April 11, 2019. He was joined in Hartford by Crew teammate Luis Argudo. Kempin made his debut for the club two days later, starting a 3–1 defeat against Pittsburgh Riverhounds SC. After appearing once more for Hartford, Kempin was recalled by the Crew on April 23. He would play five times in Columbus during the remainder of the season, including both of the Crew's matches in the 2019 U.S. Open Cup. At the end of the season, Kempin was named as the winner of the club's Kirk Urso Heart Award as the player that "best exemplified the qualities of a teammate and became 'the heart' of the Black & Gold’s locker room." Although his contract expired following the season, on October 21 it was announced that Kempin had signed a new contract with Columbus and would return to the Crew in 2020.

Kempin was born in Leawood, Kansas and attended Blue Valley North High School, winning a state title as a freshman and being inducted into the school's Athletic Hall of Fame in 2017. He played club soccer in the Kansas City Wizards system, climbing through the club's academy setup before signing for the first team as a homegrown player in August 2010. Kempin made his debut for the renamed Sporting Kansas City in May 2012, going on to appear 12 times for the team in seven seasons. He took part in the iconic "Double Post" game against Portland Timbers in the 2015 MLS Cup Playoffs. Kempin spent four spells on loan while with SKC, winning a USL Pro championship with Orlando City and also spending time with OKC Energy, San Antonio Scorpions, and Swope Park Rangers. After being released by Sporting KC, he spent a year in the LA Galaxy organization before joining Columbus Crew SC ahead of the 2018 season.

Born in Leawood, Kansas, Kempin played club soccer for the KC Legends, Blue Valley Stars, and KCFC Alliance youth teams. He attended Blue Valley North High School in Overland Park, winning a state title and allowing just two goals as a freshman. He was selected to take part in the United States U17 residency program at the IMG Soccer Academy, where he spent his sophomore year. After one season in the residency program, Kempin returned to Kansas and joined the Kansas City Wizards Academy in the U.S. Soccer Development Academy. As a junior at Blue Valley North, he was named as the Kansas State Player of the Year and as a Parade All-American. In 2017, Kempin was inducted into the Blue Valley North Athletic Hall of Fame and the Kansas Soccer Hall of Fame.

After training with the team during preseason, Kempin signed with LA Galaxy on March 3, 2017. He was intended to serve as the club's number three goalkeeper, behind Brian Rowe and Clément Diop. With Rowe injured and Diop on international duty, Kempin was handed his club debut on June 3; he made six saves in a scoreless draw with D.C. United. On August 23, in his second start of the year, he tied an MLS record by saving two penalty kicks in a match, although the Galaxy were defeated 2–0 by Columbus Crew SC. Kempin appeared nine times in all competitions on the season, but the Galaxy declined his contract option on November 27.

In a bid to find playing time, Kempin was loaned to the Galaxy's reserve team, LA Galaxy II, in the United Soccer League. He made his debut for the club on March 25, 2017, keeping a shutout in a 2–0 victory over Whitecaps FC 2. Kempin appeared for Los Dos sporadically throughout the 2017 season, playing his final game while on loan on August 2 against Orange County SC. He played six times on the year with Galaxy II.

On December 13, 2017, Kempin was traded to Columbus Crew SC in exchange for a fourth-round pick in the 2018 MLS SuperDraft. He stepped straight into the backup role behind Zack Steffen, appearing on the bench in each of Crew SC's first three matches. With Steffen off on international duty, Kempin made his debut for the club on March 24, 2018, starting against D.C. United. He made one save, helping Columbus to a 3–1 victory. He went on to appear four more times, finishing his first season in Columbus with five appearances; he was named to the bench an additional 31 times in all competitions. On December 9, Kempin had his contract option picked up by the club.

Although Kempin had been considered to be SKC's goalkeeper of the future for six years, his future with the club was thrown into doubt following the 2016 MLS SuperDraft; both Vermes and co-owner Robb Heineman said that the club wanted to draft Andrew Tarbell, and that they had viewed Tarbell as a "ten-year goalkeeper" for the club. That revelation, coupled with the selection of Alec Kann in the 2015 MLS Re-Entry Draft, meant that Kempin was again the club's number three goalkeeper. He was sent on loan to SKC's United Soccer League affiliate, Swope Park Rangers, on March 25, 2016. Kempin started the inaugural game in Swope Park history, making two saves in a 2–1 victory against Portland Timbers 2 on March 26. He made 12 appearances for the Rangers during the season, splitting time with Zac Lubin for much of the year.

Kempin spent the early part of August moving between Sporting KC and Swope Park, playing in the league while on loan and appearing on the bench for SKC. He played twice in the 2016–17 CONCACAF Champions League, with a start against Vancouver Whitecaps FC on August 23 eventually marking his 12th and final appearance with Sporting KC. Kempin had his contract option declined by the club on November 23, ending his ten-year association with the Sporting Kansas City organization. He went unselected in the 2016 MLS Re-Entry Draft.

Kempin represented the United States from U14 to U23 level. He was a part of the U17 residency program at the IMG Soccer Academy while in high school, and represented the U18, U20, and U23 teams in competitive matches. Kempin earned his only senior call-up in January 2015.

On March 20, 2015, Kempin was again sent on loan, this time joining North American Soccer League club San Antonio Scorpions for the duration of the 2015 season. SKC manager Peter Vermes said that Kempin was headed to San Antonio, instead of affiliate club OKC Energy, because "[he] has the ability to go in and be the number one right away in San Antonio." He started each of the Scorpions' first two matches on the year, conceding five total goals in defeats against Tampa Bay Rowdies on April 4 and Indy Eleven on April 18.

After Luis Marín terminated his contract with the club, Kempin was recalled to Sporting Kansas City on May 27, 2015. He spent the majority of the season backing up Tim Melia, but did appear three times in a four-match stretch in August. Kempin's only other appearance on the year came in the knockout round of the 2015 MLS Cup Playoffs, in a match that would become known as the "Double Post" game. Against eventual champions Portland Timbers, Melia suffered a head injury and had to exit the match in the 84th minute. Kempin did not concede a goal through extra time, and made three saves in the ensuing penalty shootout, but saw his kick in the 11th round saved as Portland advanced by a 7–6 scoreline. Although his contract expired at the end of the season, Kempin re-signed with Sporting KC on December 9.

In November 2011, Kempin also spent time with the U23 national team, sitting on the bench for the side during the same dual training camp in Duisburg. He made his debut, and his only appearance for the U23s, exactly four years later: against Brazil on November 11, 2015, Kempin replaced Charlie Horton and played 45 minutes in a 2–1 defeat.

Kempin earned his first, and to date only, call-up to the United States national team in January 2015, as head coach Jürgen Klinsmann included the then-21-year-old as one of four goalkeepers in the January camp squad. Kempin did not appear in either match during the camp, with Nick Rimando and Sean Johnson splitting the minutes.

On March 17, 2014, Kempin was loaned to OKC Energy FC for the duration of the 2014 season. The Energy, playing their debut season in the USL Pro, were coached by Kempin's former teammate in Kansas City, Jimmy Nielsen. Kempin made his club debut on April 7, starting in a 4–2 defeat against LA Galaxy II. He appeared 13 times through the front half of the season, with that run of matches including a six-game losing streak and a six-game unbeaten run.

Kempin was recalled by Sporting KC on July 9, 2014, after Eric Kronberg fractured a bone in his left hand. He immediately stepped into the backup role behind Andy Gruenebaum, sitting on the bench in SKC's next five matches. Kempin was selected to take part in the inaugural MLS Homegrown Game, where he played the second half against Portland Timbers U23s and was named as the game's Most Valuable Player. Just five days after the Homegrown Game, Kempin stepped in to make his Major League Soccer debut; Gruenebaum went out injured against Vancouver Whitecaps FC on August 10, leaving Kempin to take over at halftime. He saved a penalty from Darren Mattocks in the 85th minute, but Sporting KC fell by a 2–0 scoreline. Kempin went on to appear in SKC's next four games, including a match against Real Estelí in CONCACAF Champions League play on August 20. Although he returned to the bench following Gruenebaum's return to health, Kempin finished the season with five appearances for Sporting Kansas City.

On March 14, 2013, Kempin was loaned to Sporting KC's USL Pro affiliate Orlando City in a bid to find regular playing time. The loan was for the duration of the 2013 season, with the club able to recall him at any time. Kempin made his Orlando debut, and his professional league debut, on April 7, starting a 3–1 victory against Phoenix FC. He appeared nine times for the Lions on the year, playing for the last time in a scoreless draw with Pittsburgh Riverhounds on July 17. Kempin did not appear in the club's playoff run, with Miguel Gallardo starting in net as Orlando claimed the USL Pro title for the second time in club history.

Kempin returned to Sporting Kansas City with six games remaining in the regular season, but was unable to beat out Jimmy Nielsen or Kronberg to make a matchday squad. He watched on during the club's playoff run as SKC defeated Real Salt Lake on penalties to win MLS Cup 2013, the second league championship in club history.

Kempin spent time with the U20 national team in November 2011, taking part in a dual training camp in Duisburg, Germany without appearing in a game. He earned his only cap at U20 level more than a year later, playing in a friendly against Panama on January 21, 2013. Kempin replaced Kendall McIntosh at halftime and conceded both goals in a 2–1 defeat.

In his third professional season, Kempin finally made his debut for SKC. On May 29, 2012, he started against Orlando City in the U.S. Open Cup, making six saves and helping Sporting KC claim a 3–2 victory. He was named to the bench 13 times in league play, all due to an injury to normal backup goalkeeper Eric Kronberg, but did not play outside of his lone cup appearance.

After previously spending time with the U14 national team, Kempin was called up for the first time by the United States U18s on April 11, 2011. He was one of two professional players called into a training camp in Portland, Oregon, the other being Victor Pineda. Kempin went on to appear three times on the year for the U18s, playing twice in the Lisbon International Tournament and once at the Milk Cup.

On August 31, 2010, Kempin signed with the Kansas City Wizards as the first homegrown player in club history. At 17 years old, he was the youngest player ever signed by the Wizards. Kempin did not make an appearance in his first professional season, although he was named to the bench for the club's season finale against San Jose Earthquakes. In 2011, Kempin again did not play for the Sporting Kansas City first team. He did become the club's primary goalkeeper in the MLS Reserve League, appearing several times in that competition, and was named to the substitutes' bench three times in Major League Soccer play.

Jonathan Kempin (born April 8, 1993) is an American professional soccer player who plays as a goalkeeper for USL Championship club San Diego Loyal, on loan from Columbus Crew SC. He previously appeared for Sporting Kansas City (SKC) and LA Galaxy and spent time on loan with Orlando City, OKC Energy, San Antonio Scorpions, Swope Park Rangers, LA Galaxy II, and Hartford Athletic.