The film was a box office disappointment when it was released, perhaps due in large part to it being given a theatrical release around the same time as The Lion King and Forrest Gump.
Billy Heywood (Luke Edwards), a Little League Baseball player, is a pre-teen son to a widowed single mom, Jenny (Ashley Crow). Billy's grandfather is Thomas Heywood (Jason Robards), owner of the Minnesota Twins.
The Twins are a last-place team, but Billy and his grandfather love each other, the Twins, and the game of baseball. When the grandfather dies, it is revealed that he wants Billy to inherit the franchise. Thomas Heywood specified that if Billy is still a minor at the time of his death, his aides are to help him until Billy is old enough to run the team by himself.
Billy quickly runs afoul of the team's manager, George O'Farrell (Dennis Farina). Billy believes he is too hard on the players. O'Farrell despises the idea of working for a kid and balks at a potential signing of superstar player Rickey Henderson much to Billy's frustration. After O'Farrell insults Billy and tells him to butt out of the team's business, Billy fires him.
There is considerable difficulty finding another manager to replace O'Farrell, since no one particularly wants to work for a kid. Billy therefore decides to name himself the new manager after one of his friends points out, "It's the American League! They got the DH! How hard could it be?" He reaches out to the Commissioner of Baseball, who approves after consulting with Jenny. (In real life, for conflict of interest reasons, MLB does not allow team owners to make themselves their team's manager, though the commissioner can grant an exception.)
The players are very skeptical, but Billy promises that if he does not improve the team's position in the standings within a few weeks, he will resign. The team quickly moves up to division race contention. Unfortunately, not all is going smoothly for Billy, as his friend and star first baseman Lou Collins (Timothy Busfield) takes a romantic interest in Billy's mother.
Billy picks up bad habits on the road, and is even ejected from a game and given a one game "suspension" by his mother for throwing a temper tantrum and swearing at an umpire because of a call he didn't like. He also must release his personal favorite Twins player, Jerry Johnson (Duane Davis), who is clearly in the twilight of his career. He ends up making Jerry feel even worse when Billy immaturely tries to illustrate his own distress by pointing out he owns Jerry's baseball card and wouldn't give it up for a Wade Boggs and a Sammy Sosa.
The pressures of managing the team while also fulfilling his other responsibilities, such as schoolwork, wear him down and consume his free time. Billy's friends do not like how Billy's managerial responsibilities are keeping him away from being with them. Even when he's physically present (as opposed to on the road with the team), he is typically distracted by team business.
Lou goes into a slump and the jealous Billy benches him, sending the Twins into a losing skid. Billy later tells his mom that he's tired of being a "grown-up" and decides to quit as manager after the end of the season, even reinstating Lou to starter on first base.
Down four games in the wild card race with four games left to play, the Twins win all four. In contrast, the first place Seattle Mariners lose four straight, forcing a one-game playoff to determine who advances to the postseason.
The two teams trade three-run home runs during the course of the game, and extra innings is required, however the Mariners eventually retake the lead. Down to their final out, Lou tells Billy while on-deck that he asked his mom to marry him. He says her reply was to ask Billy. With a runner on base, Billy says if Lou hits a homer (which would win the game), he will give his blessing, but quickly relents and gives Lou his consent whether or not he hits a homer. Facing Randy Johnson, Lou hits a long fly ball to center field, but Ken Griffey Jr. makes a leaping catch at the wall to rob Lou of a homer, and the Twins lose.
With their season over, Billy tells the players he is officially stepping down as manager, with pitching coach Mac MacNally (John Ashton) taking his place, as well as bringing back Jerry to be the third base coach and new hitting instructor (thereby, implying that Johnson retired as an active player). The players object, but Billy reassures all the players that he will still be the owner, and says that he might come back as manager if junior high doesn't work out. When being informed that none of the fans have left, Billy, along with the rest of the team, returns to the field to receive a standing ovation from everyone in the Hubert H. Humphrey Metrodome.Luke Edwards as Billy Heywood
Timothy Busfield as Lou Collins, 1B
John Ashton as Mac Macnally
Ashley Crow as Jenny Heywood
Kevin Dunn as Arthur Goslin
Billy L. Sullivan as Chuck
Miles Feulner as Joey
Jonathan Silverman as Jim Bowers
Dennis Farina as George O'Farrell
Jason Robards as Thomas Heywood
Wolfgang Bodison as Spencer Hamilton
Duane Davis as Jerry Johnson
Leon Durham as Leon Alexander, 1B
Kevin Elster as Pat Corning, SS
Eric Gendreau as Himself
Joseph Latimore as Lonnie Ritter, LF
Brad Lesley as John 'Blackout' Gatling, RP
John Minch as Mark Hodges, Catcher
Michael Papajohn as Tucker Kain, CF
Scott Patterson as Mike McGrevey, SP
Troy Startoni as Larry Hilbert, 3B
Antonio Lewis Todd as Mickey Scales, 2B
O'Neal Compton as Major League umpire
John Gordon as Wally Holland
Chris Berman as Himself
Ken Griffey, Jr as Himself
Randy Johnson as Himself
Lou Piniella as Himself
Dave Magadan as Himself
Paul O'Neill as Himself
Rafael Palmeiro as Himself
Iván Rodríguez as Himself
Wally Joyner as Himself
Mickey Tettleton as Himself
Eric Anthony as Himself
Carlos Baerga as Himself
Sandy Alomar Jr. as Himself
Alex Fernandez as Himself
Lenny Webster as Himself
Dean Palmer as Himself
Tim Raines as Himself