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Andrew McCutchen had a difficult season in 2016, but he bounced back to hit .279 with 28 home runs for the Pittsburgh Pirates in 2017. He will replace Denard Span in the outfield for the San Francisco Giants. Credit Ross D. Franklin/Associated Press

The Pittsburgh Pirates chose Andrew McCutchen in the first round of the draft in 2005, when they were deep into a two-decade stretch of losing. McCutchen was in high school then, and as he nurtured his talent in the Pirates’ farm system, the franchise slowly stirred to life. In 2013, when the Pirates returned to the playoffs for the first of three consecutive trips, McCutchen was the National League’s Most Valuable Player. His contract bound him to Pittsburgh for years to come.

Now he is on his way out, as the latest Pirates mainstay to be traded this month. Two days after shipping starter Gerrit Cole to the Houston Astros, the Pirates traded McCutchen to the San Francisco Giants on Monday for reliever Kyle Crick, the outfield prospect Bryan Reynolds and $500,000 in international bonus-pool money.

Early Monday evening, McCutchen said goodbye to Pittsburgh with a message on Twitter: “Pittsburgh. My Home. My Fans. My City. The placed that raised me and helped mold me into the man I am today. You will 4ever be in my heart. A tip of the cap to all who have been on this journey with me. With Love and respect, Cutch.”

McCutchen, 31, is eligible for free agency after this season, in which he will make $14.5 million in the option year of a bargain contract he signed in 2012. He hit .279 with 28 homers and an .849 on-base plus slugging percentage last season and replaces Denard Span in the Giants’ outfield. The Giants, who are reloading after a surprising last-place finish, dealt Span to Tampa Bay last month as part of their trade package for third baseman Evan Longoria.

The Pirates have regressed since winning 98 games and the top N.L. wild card in 2015, falling to 78 wins in 2016 and 75 last season. Along the way, they traded some pillars of their recent playoff teams, including second baseman Neil Walker and closer Mark Melancon. But trading Cole and McCutchen signals a determined emphasis on the future, and the end of an exciting but unfulfilling era.

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The Pirates beat the Cincinnati Reds in the 2013 wild card game, but then lost a five-game division series to St. Louis. They were shut out at home in the next two wild card games, by the Giants’ Madison Bumgarner in 2014 and the Chicago Cubs’ Jake Arrieta in 2015.

Their retreat may not last long. The Pirates control closer Felipe Rivero, left fielder Starling Marte, first baseman Josh Bell and right fielder Gregory Polanco for at least four more seasons each. They have promising young starters in Jameson Taillon and Trevor Williams in their rotation, and will plug Joe Musgrove, acquired from the Astros, into Cole’s spot.

Austin Meadows, the Pirates’ top prospect, could win an outfield job with McCutchen gone, and Colin Moran, a former first-round pick who also arrived via the Houston trade, could challenge the veteran David Freese at third.

But for now, the Pirates are confronting the grim reality of history repeating itself. Though McCutchen is not leaving as a free agent, he is heading to the same team a different homegrown Pirates outfielder and former M.V.P. joined 25 years ago.

That player, of course, was Barry Bonds.

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