Red Sox’s David Ortiz Signing Lands Among Best Free Agent Deals Ever

The Boston Red Sox have had some hits in free agency over the years. Of course there have been some misses, like Pablo Sandoval, but there have been a lot of wins.

When you think about the best moves in free agency in recent memory, there is one that transformed the franchise more than every other one: David Ortiz. Boston brought Big Papi to town ahead of the 2023 season and the rest is history. 10 All-Star nods, three World Series titles, a trip to the Hall of Fame. Let's also not forget that he was integral to potentially the greatest comeback in professional sports history when Boston came back after being down three games to none against the New York Yankees in the 2004 American League Championship Series before moving on to break the Curse of the Bambino in the 2004 World Series against the St. Louis Cardinals.

Ortiz wasn't just one of the greatest additions in free agency in Boston history, but big league history in general. ESPN's Bradford Doolittle shared a column on Friday ranking the greatest move in free agency history and had Ortiz ranked at No. 3 all-time behind just Barry Bonds and Greg Maddux.

The Red Sox made one of the best moves in MLB history

Sep 13, 2025; Boston, Massachusetts, USA; Current FOX Sports analyst and former Boston Red Sox designated hitter David Ortiz throws out the first pitch before a game between the Boston Red Sox and the New York Yankees at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

"No. 3. David Ortiz (818.3 points)," Doolittle wrote. "First year: 2003 | Team: Red Sox. Initial terms: 1 year, $1.3 million | bWAR: 34.2. You can quibble whether this one belongs, but I'm keeping it. Ortiz wasn't a free agent because he reached any service time requirement, but because the Twins released him, at age 26, even though he was coming off his best season (20 homers, 120 OPS+).

"Papi finished fifth in AL MVP voting in his first Boston season and kept re-signing and extending until he finally reentered free agency after the 2011 season. By then, he was a legend. And, of course, he never left the Red Sox."

The Red Sox have had plenty of talented players over the years. There was star power all over the place on those World Series teams but there hasn't been another player who transformed the franchise like Ortiz did.

To this day, Ortiz is always involved with Boston in some way. When he came to Boston, the Red Sox needed a slugger. But he also needed a team to believe in him as well. He hit 20 homers and drove in 75 runs with the Twins in 2002. Those are solid numbers but they moved on. Boston got him on a cheap deal and that's when he went from "David Ortiz" to "Big Papi." He needed Boston and the Red Sox needed him the same. It was a perfect marriage and helped to put the club back on the map.