Smith went on to become the owner of several professional sports teams, including the National Champion and European Champion
Manchester Spartans. In July 1999, he bought financially struggling English League club
Chester City, making him the first American owner, chairman, and chief executive in the history of European football. He declared his belief that the club could reach
Division One (now the
EFL Championship) within three years. The club was in administration when he took over, and close to folding with more than £1 million in debt. He was credited with rescuing Chester from the brink of bankruptcy by supporters at the time, and announced an intention to appoint three supporters to the club board of directors, which he did. At the time of Smith's takeover, most veteran players had been sold and the remaining players were mostly young. He kept these young players and tried to develop them in order to keep the player wages low, so that the club could not only balance the budget for that season, but also so they could try to pay off the £1 million of debt that Smith inherited. Using this low budget strategy, along with increasing revenue through good Cup runs in the
FA Cup and the
Worthington Cup, increased attendance and commercial advertising, and with Smith serving as both manager and general manager for free at no cost to the club, then Smith was able to get all the club's debts paid off within only five months, which was two and a half years earlier than the administration required. As a result, the club was out of debt for the first time in at least many decades. In Smith's four months and 21 league matches in charge of team affairs, Chester managed wins against
Brighton & Hove Albion,
Shrewsbury Town and others, but lost 5–1 and 4–1 to
Leyton Orient and
Carlisle United respectively, and required a replay to overcome non-league minnows
Whyteleafe in the
FA Cup. However, they did find success in the Worthington Cup, beating First Division
Port Vale 6–5 on aggregate; they won 2–1 at the
Deva Stadium in a game which saw both
Marcus Bent and
Martyn Lancaster sent off, and then drew 4–4 in the return leg at
Vale Park. They also had success in the FA Cup, as they made it to the third round for just the third time in the club's 100-year history. Drawn against
Manchester City, they only lost in the final minutes after the score was tied at 1–1 with eleven minutes left. While scouting Man City ahead of the match, Smith, who came up with a very good strategy and team plan for the Man City match, found that when he could watch a match from up in the stands, then he was able to see the necessary tactical adjustments because of his many years of experience coaching American football, where coaches scout opponents by spending hundreds of hours every season watching game footage of their opponents that is filmed from high in the stands. This skill would benefit the team considerably the following season, when Smith would scout all of Chester's impending Cup opponents. His methods included saying aloud the
Lord's Prayer during his pre-match team talk, preparing lengthy written strategic game plans for each match that he went over in his pre-match team talk and gave copies of to each player, always staying positive no matter the current difficulties and circumstances, developing a school program where he went with players to speak with and coach schoolchildren, and to give out free tickets to each child for the upcoming matches, and appointing captains for the defence, midfield and attack. In late December 1999, with Chester out of debt and on firm financial footing for the first time in decades thanks to Smith's tight monetary policies, Smith chose to step down as manager. His decision came only one match after his team had pulled itself off the bottom of the Division following a 2–1 win over
Halifax Town. Smith hired veteran manager
Ian Atkins to the dual role of director of football and manager in a bid to avoid relegation, while Smith himself took on the role of goalkeeper coach for the remainder of the season. With the excellent improvements in the club's financial position, the club was able to sign twelve new players that Atkins wanted and chose, doubling the player wage bill compared with when Smith was manager. The club was also able to afford to pay for team travel by luxury coaches to away matches instead of the regular buses used during Smith's period, and was able to pay for the team to stay at top hotels with excellent pre-match meals for all away matches instead of traveling to matches by bus on match day as had occurred during Smith's time period. The club also paid for a proper training facility with two excellent training pitches for Atkins' team, while Smith's team had endured training on a free piece of unlined grass in the middle of a horse racetrack. However, despite these many financial investments in the team, the team began slowly under Atkins, losing seven of his first nine matches in charge, with only one win and one draw, and falling well adrift at the bottom of the Division table. Atkins' team lost his ninth match in charge by a 7–1 score at home to Brighton & Hove Albion, even though Smith's young team had defeated Brighton 3–2 away at Brighton earlier in the season. Afterwards, however, results began to improve, and a 5–0 home victory over Mansfield Town in April, where Smith signee Angus Eve, Trinidad & Tobago's career leading goal scorer with 43 national team goals, scored two goals, put Chester in a better position. Going into the final game of the season, Chester had pulled themselves up to 23rd in the 24-team division, and faced a three-way battle with Shrewsbury Town and Carlisle United to avoid the drop to the
Conference. With fifteen minutes left in the season, Chester were above both Shrewsbury and Carlisle, but conceded a late goal against
Peterborough United that was enough to see them relegated from the Football League on goal difference. Atkins left, and fan favourite
Graham Barrow returned as manager. He completely rebuilt the team, and in the 2000–01 season, his side managed a respectable ninth place, reached the third round of the FA Cup for the second successive season (in a controversial loss to Blackburn Rovers), made it to the semi-finals of the
FA Trophy, and won the
Conference League Cup, the first silverware for the club in over 70 years. During the season, Smith served as Barrow's scout and set-piece strategist for all Cup opponents, travelling on his own to scout opponents at least once or twice before Chester played them. In this scouting role, Smith utilized his American football background, where every American Football play is planned and choreographed from a set position in intricate detail, to focus on the development of creative set pieces, both corners and free kicks, for all the Cup matches that were based upon the weaknesses he perceived in the opponents' defensive alignment. In addition, Barrow approached Smith at the start of the season, and asked him to watch the first half of every Chester match from up in the stands as a scout would, and then report what he saw to Barrow at halftime while Barrow was walking from the pitch to the dressing room. This good working relationship between them continued throughout the season. In spite of this success, ahead of the
2001–02 season, Smith appointed
Gordon Hill, an ex-Manchester United and ex-England player who was a personal friend, to become the new manager. Chester made a dreadful start to the season under Hill, winning only one of their first twelve matches. Smith finally sold his interest in the club to
Stephen Vaughan and left at the start of October 2001, with the club completely out of debt other than what it owed him. In 2003, a British court ordered Chester City to repay £300,000 in unpaid loans to Smith and his family. However, Smith still wanted to help the club, and so he accepted a settlement of far less than half that amount. In 2004, Chester City FC finished first in their division, and was promoted again into the English League Third Division, thereby at that time fully completing the financial and on-field renovation of the club that had begun when Smith first purchased the club in an effort to rescue it from being closed down in 1999.
AppleMagazine.com wrote in its April 23, 2021 edition that
Ted Lasso "was actually inspired by the story of Terry Smith, an American gridiron football coach who took over the English association football team Chester City F.C. and subsequently installed himself as the first-team coach". The writers and actors of the Ted Lasso series often spoke about Terry Smith before the series began. In this interview and AppleTV+ video, Brendan Hunt, the outstanding co-creator of Ted Lasso, and actor who portrays assistant manager Coach Beard in the Ted Lasso series, discusses a 1999 FourFourTwo soccer magazine article about Terry Smith selling the American dream in a positive way, including a photo in the article of Smith wrapped in an American flag. This 22 year-old magazine article was published in England in September, 1999, when Smith was being the first American to ever manage and coach a professional English soccer team. In March 2025, Smith purchased the
Brantford Red Sox, a legendary 115-year-old professional baseball team in Ontario Canada's
Intercounty Baseball League that has won a record 15 League Championships, but has been struggling in last place and near financial closure for the past several years. With six home games remaining in the 2025 season, the Red Sox were on a ten-game losing streak and had a home record for the entire season of one win and fourteen losses, with a thirteen-game home losing streak. It was at this low point that Smith took over as the team's manager/head coach, and his Red Sox team responded by going undefeated and winning all six of its remaining home games with Smith as manager, the longest home winning streak the Red Sox team has had since 2004. ==Personal life==