The 10 biggest what-if MLB trades that never happened since 2000

NEW YORK - APRIL 18: Alex Rodriguez #13 of the New York Yankees looks on against the Texas Rangers at Yankee Stadium on April 18, 2010 in the Bronx borough of Manhattan. The Yankees defeated the Rangers 5 - 2. (Photo by Rob Tringali/Sportschrome/Getty Images)
NEW YORK - APRIL 18: Alex Rodriguez #13 of the New York Yankees looks on against the Texas Rangers at Yankee Stadium on April 18, 2010 in the Bronx borough of Manhattan. The Yankees defeated the Rangers 5 - 2. (Photo by Rob Tringali/Sportschrome/Getty Images) /
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BOSTON, MASSACHUSETTS – SEPTEMBER 29: Mookie Betts #50 of the Boston Red Sox looks on after the Red Sox defeat Baltimore Orioles 5-4 at Fenway Park on September 29, 2019 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)
BOSTON, MASSACHUSETTS – SEPTEMBER 29: Mookie Betts #50 of the Boston Red Sox looks on after the Red Sox defeat Baltimore Orioles 5-4 at Fenway Park on September 29, 2019 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images) /

MLB what-if No. 7: 2015 — Mookie Betts to the Philadelphia Phillies

Heading into the 2015 season, it was clear that the Phillies were steering towards a complete rebuild. Team cornerstones Ryan Howard, Chase Utley, and Carlos Ruiz were far from their prime days and each seemed projected to depart in the coming seasons. However, they had 31-year-old Cole Hamels, who still could produce All-Star caliber seasons and had the highest trade value on the team.

Phillies General Manager Ruben Amaro Jr. engaged in trade talks with several teams for Hamels, including the Red Sox. Amaro Jr. — like any other GM would — began talks off by asking for as much possible in the deal. He inquired for both outfielder Mookie Betts and catcher Blake Swihart, but Boston refused to include either in any proposed deal.

Talks did not go very far after that as Boston decided to hold onto their array of coveted prospects and wait until free agency to add an ace, which was the best possible decision they could have made. Boston wound up signing David Price and then brought in Chris Sale a year later — both of whom were crucial in the team’s 2018 World Series title run. Mookie Betts later became a five-tool, franchise superstar who won AL MVP honors in 2018.

While Boston’s patience paid off in the end, the Phillies’ aggressiveness garnered them poor results. They later settled on trading Hamels to the Rangers at the 2015 trade deadline for five players — all of whom have combined to net the Phillies a combined 5.6 bWAR. Had Amaro Jr. decided to take a step back, scour the Red Sox farm system and ask for players like Michael Kopech or possibly Rafael Devers, the Phillies may have received a return far greater than what they actually got.

In the big picture, this deal would have changed the complexion of baseball today. The Red Sox might not have pulled off their 2018 title run. With the Phillies content with Betts’ production, they very likely would have had zero interest in Bryce Harper. And with Boston in need of a right fielder, Harper could have wound up signing with them last year. With Betts locked up in Philly, The Dodgers wouldn’t have been able to trade for him.

Just some of the many what-if domino effect scenarios that come with such a trade like this one.