Manny Machado was one of the two biggest prizes on MLB's free agent market. Only Bryce Harper remains. (Elise Amendola/Associated Press, File)

For more than three months they have circled each other, 26-year-old superstars with the same objective: Sign a massive, industry-standard free agent contract. Manny Machado and Bryce Harper are friends, but this winter they were also competitors, as their respective agents worked the markets with one eye on the other in a high-stakes game of chicken, with the winner the man who emerges with the bigger deal.

Now that Machado has come off the board, having reportedly agreed with the San Diego Padres on Tuesday to a 10-year, $300 million contract — for now, at least, the largest for a free agent in American sports history — the final say will belong to Harper and agent Scott Boras. And there is every reason to think their answer, as teams prepare for their first exhibition games this week, is coming soon.

Machado’s massive deal — which remains unofficial pending a physical — brought to a close half of baseball’s twin offseason dramas: the simultaneous pursuits of two of the most highly coveted free agents in recent history. The Machado contract surpasses Alex Rodriguez’s 2007 deal with the New York Yankees (10 years, $275 million) as the largest for a free agent in history — although the 13-year, $325 million extension Giancarlo Stanton signed with the Miami Marlins in 2014 remains the largest overall deal.

The Padres, who haven’t made the playoffs since 2006 and lost 96 games last season, may have been a surprise suitor at the start of the winter, but they were a steady presence at the front of the market for Machado all offseason.

Boasting the game’s best farm system, with no fewer than 10 of the game’s top 100 prospects, according to MLB Pipeline, the Padres already had a glowing future but saw an opening in both the National League West and their own metropolitan area — where the departure of the NFL’s Chargers left them as the only major sports franchise in town — to strike now.

The $300 million they are set to give Machado more than doubles their previous biggest free agent signing — the $144 million they handed Eric Hosmer a year before, which was also the industry’s largest of the winter — but gives them a superstar cornerstone to surround with their wealth of young talent. Their 2019 payroll was at less than $80 million before the Machado signing.

Machado’s deal reportedly contains a player opt-out clause after five years, which would permit him to return to free agency at the end of 2023, when he would be 31. Machado had expressed a preference to play shortstop in his dealings with prospective teams but probably will be a third baseman in San Diego. Fernando Tatis Jr., ranked by MLB Pipeline as the No. 2 prospect in baseball, is the Padres’ shortstop of the future.

The Chicago White Sox appear to have been the runners-up for Machado, reportedly offering a guaranteed $250 million over eight years, but with options and incentives that could have boosted the overall payout to $350 million by the end of the deal. But Machado and agent Dan Lozano took the higher, record-setting guarantee.

“This morning,” White Sox President Ken Williams told reporters Tuesday, “I honestly believed we had the best offer on the table.”

The Padres had also shown interest in Harper, the former Washington Nationals right fielder, meeting with him and his representatives in January in Harper’s hometown of Las Vegas, but it is not known whether they submitted a firm offer.

With many of baseball’s traditional big spenders — the New York Yankees, Boston Red Sox, Los Angeles Dodgers and Chicago Cubs — largely staying out of the Machado and Harper sweepstakes, their markets were largely confined to the same group of teams: the Padres, White Sox, Philadelphia Phillies and, at least in the case of Harper, the Nationals and San Francisco Giants.


Harper still needs to make a decision. (Nick Wass/Associated Press, File)

As a result, Harper’s ultimate landing spot is likely to come out of that group, and it is the Phillies — whose owner, John Middleton, declared to USA Today in November his willingness to be “a little stupid” with his spending this winter — who have been widely viewed for weeks as Harper’s likeliest destination.

Phillies General Manager Matt Klentak, speaking to reporters Tuesday, said the reported terms of the Machado deal “will exceed our valuations” — adding, “sometimes you have to be willing to walk away” — but did not pull his team out of the Harper sweepstakes.

Machado, drafted by the Baltimore Orioles two spots behind Harper in 2010, has been one of baseball’s best all-around players since debuting at Camden Yards on Aug. 9, 2012, amassing 175 home runs, four all-star appearances and two Gold Gloves (both as a third baseman) in parts of seven seasons while averaging 4.8 wins above replacement (per Baseball-Reference) per season.

Aware they had no chance of retaining him, the Orioles dealt Machado to the Dodgers for prospects at last year’s trade deadline, and he helped Los Angeles advance to the World Series. But he also did his free agency no favors by telling Fox Sports during an interview in October that he was “not the type of player that’s going to be ‘Johnny Hustle’ ” — a self-characterization that, even after he attempted to clarify the remarks, confirmed for many the widespread view that he was not a team player.

Perhaps tellingly, the Dodgers, despite being one of the richest teams in the game in terms of revenue, made almost no effort to retain Machado at the end of 2018.

For weeks, the continued unemployment of Machado and Harper had been a high-profile flash point in the deteriorating relations between Major League Baseball and its players association over the trajectory of free agency, and parties on both sides were anxious to end the drama.

For the second straight winter, the market was slow to develop, and a handful of elite free agents lasted until after the opening of spring training camps. In addition to Harper, the list of those still unsigned as of Tuesday evening includes 2015 AL Cy Young Award winner Dallas Keuchel and seven-time all-star closer Craig Kimbrel.

Interestingly, the deal Machado reached with the Padres was the precise contract offer the Nationals made to Harper in November (although deferrals could have reduced its present-day value), which Boras rejected and the Nationals later withdrew.

Boras has touted Harper, the 2015 MVP, as a generational talent and has floated numbers as big as $400 million as a potential target in the past, but those ambitions have bumped up against an industry largely retreating from long-term deals for veteran players. Some teams may have jumped at the chance to get Harper on a shorter-term deal — perhaps even at a higher average annual salary than Zack Greinke’s record $34.4 million with the Arizona Diamondbacks — but Harper and Boras were thought to be holding out for a longer deal.

Any day now, the rest of baseball will find out whether all that posturing, all that work and all that waiting by Harper and Boras were worth it.

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