Major League

Former Las Vegas showgirl Rachel Phelps (Margaret Whitton) has inherited the Cleveland Indians baseball team from her deceased husband. Phelps has received a lucrative deal to move the team to Miami, and she aims to trigger the escape clause in the team's contract with Cleveland if season attendance falls below minimum levels. To do this, she replaces their existing players with aging veterans and inexperienced rookies, hoping a bad team will cause attendance to decline. Phelps hires Lou Brown, a former coach from the Toledo Mud Hens to manage the team.
During spring training in Tucson, Brown and veteran catcher Jake Taylor discover the new team has a number of interpersonal issues as well as their own struggles with the game, such as the prima donna nature of Roger Dorn, the only player on a long-term contract with the Indians, and the weak arm of veteran pitcher Eddie Harris who is forced to doctor his pitches to stay competitive. The team starts the season on a losing streak. Their rookie pitcher, Ricky Vaughn, has an incredible fastball but with little control, leading him to be called "Wild Thing"; however, by chance, Brown discovers Vaughn has eyesight problems, and when they fit him with glasses, his pitching drastically improves, helping the Indians to a series of wins. The team rallies, bringing the Indians higher in the division standings. Phelps tries to demoralize the team by taking away their luxuries such as a private jet, but the team still holds strong, and appears to have a shot at winning the division. Meanwhile, Taylor finds that his ex-girlfriend Lynn is living in Cleveland, and tries to get her to come back to him even after learning she has become engaged to a new beau.
When Phelps' original plan falls through, she decides that she will purposely void the contract, despite the financial penalty, and will move the team to Miami regardless. Donovan relays this to Brown, who informs the team that no matter how well they do, they will be fired after the season. The team succeeds in tying the division with the New York Yankees, leading to a one-game playoff to determine the title. In the playoff in Cleveland, the Yankees take an early lead but Pedro Cerrano is able to overcome his inability to hit a curveball, hitting out a home run to tie the game. In the top of the 9th, with the bases loaded, Vaughn manages to strike out the Yankees best hitter, sending the Indians up to bat.
With the game tied and the Indians with two outs, the speedy Willie "Mays" Hayes manages a single to get on base, and then steals second. Taylor steps up, and after signalling to Brown, calls his shot to center field. With the Yankees prepared for the long play, Taylor instead bunts, allowing Hayes to make it to home safely and win the game. As the team celebrates, Taylor sees Lynn in the stands, no longer wearing her engagement ring. The two rush to hug each other as the city celebrates the victory.
Alternate ending[edit]
The theatrical release's ending includes Rachel Phelps, apparently unable to move the team because of increased attendance, angry and disappointed about the team's success. An alternate ending on the "Wild Thing Edition" DVD shows a very different characterization of Phelps.[3] Lou tenders his resignation and tells Phelps that he can't in good conscience work for her after she sought to sabotage the team for her own personal gain. Phelps then tells him that, in fact, she loves the Indians and never intended to move them. However, when she inherited the club from her late husband, it was on the brink of bankruptcy. Unable to afford top flight players, she decided to take a chance on unproven players from the lower leagues, whom she personally scouted, and talented older players who were generally considered washed up. She tells Lou that she likewise felt that he was the right manager to bring the ragtag group together.
Phelps conceived the Miami scheme and adopted a catty, vindictive persona to unify and motivate the team. As the players believed that she wanted the Indians to fail, she was able to conceal that the team could not afford basic amenities such as chartered jet travel behind a veil of taking them away to spite the players.
Lou does not resign, but Phelps reasserts her authority by saying that if he shares any part of their conversation with anyone, she will fire him.
This alternate ending was actually the original ending and was filmed and shown to test screening audiences before the movie's release. The producers said that although the twist ending worked as a resolution to the plot, they scrapped it after preview audiences responded negatively, preferring the Phelps character as a villain.

Question: Who is trying to win back an ex-girlfriend who is engaged and living in Cleveland?
Answer: Jake Taylor