These are the best free-agent SP signings of all time

January 11th, 2024

The big money for free agents, at least most of the time, goes to the hitters, all the way back to when the Yankees signed Reggie Jackson for five years and $3 million after the 1976 season -- it seemed at the time as if George Steinbrenner had not only paid Reggie that money, but he had thrown in parts of the New York City skyline.

But almost every year it is pitchers who feel like the big game -- and big gamble -- at this time of year. The Dodgers signed Yoshinobu Yamamoto for $325 million, and now we all wait to see where Blake Snell, who already has two Cy Young Awards in the books, and Jordan Montgomery, who just helped pitch the Rangers to the World Series, are going to end up.

Because so much of the conversation in baseball right now is about guys like that still being available, we thought we would make up our own Top 10 list of the best all-time free-agent starters.

1. Randy Johnson, D-backs

4-year, $52 million contract before 1999 season

The Big Unit was already 35 years old when the D-backs signed him. What Johnson did for Arizona was pitch like Sandy Koufax across his first four years with the team. He won four straight Cy Young Awards over the course of a four-year deal, had a record of 81-27, pitched the team to what is still its only World Series title, in 2001 against the Yankees. All he did in that one was win Game 6 as a starter and come out of the bullpen in Game 7. The gold standard is what he was.

2. Greg Maddux, Braves

5-year, $28 million contract before 1993 season

The Braves signed Maddux after the 1992 season, for which he won his first career Cy Young Award. Over the next 11 seasons, Maddux won 194 games for Atlanta and four more Cy Young honors. The Braves played in three World Series while Maddux was with them, and won one.

3. Nolan Ryan, Astros

4-year, $4.5 million contract before 1980 season

Ryan signed with the Astros in 1980 after leaving the Angels. Across the 1980s, he continued to strike out the world, broke Walter Johnson’s all-time record for strikeouts and helped pitch the Astros into the postseason for the first two times in the team’s history. He also threw the fifth of a record seven career no-hitters. In his final season with Houston (1988), at the age of 41, he pitched 220 innings and struck out 228 batters.

4. CC Sabathia, Yankees

7-year, $161 million contract before 2009 season

CC got to New York in 2009 and immediately helped the Yankees win what is still the only World Series they’ve won since 2000. He compiled a 134-88 record as a Yankee. Even in 2017, when he clearly wasn’t what he’d been when he was young, he had a 14-5 record, and manager Joe Girardi gave him the ball in Game 7 of the American League Championship Series against the Astros.

5. Max Scherzer, Nationals

7-year, $210 million contract before 2015 season

Max was another pitcher who proved that you can spend big on a free-agent starter after his 30th birthday. Scherzer left the Tigers, with whom he won the 2013 AL Cy Young Award, and he was even better in Washington. He would win two more Cy Young Awards for the Nationals before they traded him to the Dodgers, and he was the starter in Game 7 of the only World Series the Nats have ever won.

6. Gerrit Cole, Yankees

9-year, $324 million contract before 2020 season

Cole has been everything the Yankees hoped he would be, and more, since they signed him for $324 million after he left the Astros. He has a 51-23 record with the Yankees, he’s made 30 or more starts in all of his full seasons with New York, he has struck out 816 batters in 663 innings, and he just won his first Cy Young Award. There is no more valuable pitcher in the sport.

7. Roger Clemens, Blue Jays

4-year, $40 million contract before 1997 season

Another member of the 300-win club on this list, and someone else who was a free agent more than once. Roger didn’t last long in Toronto after leaving the Red Sox, but you have to say the Jays got their money’s worth while he was there: 41-13 record, two straight Cy Young Awards.

8. Mike Mussina, Yankees

6-year, $88 million contract before 2001 season

The Yankees signed Mussina for six years after he left the Orioles, and he was still enough of a star at the end of that deal that they signed him for two more. He went 123-72 with the Yankees, won 20 games for them in his last season at the age of 39 and went home to Pennsylvania before ending up in Cooperstown.

9. David Cone, Yankees

3-year, $19.5 million contract before 1996 season

The Yankees re-signed Cone when he became a free agent after the 1995 season. Even with an aneurysm in his right shoulder in ’96, he came back for September and got the ball from Joe Torre against the Braves in Game 3 of the World Series in Atlanta when the Yankees were down 0-2. In ’98, he went 20-7 for the greatest Yankees team of them all. And oh, by the way, he pitched a perfect game in ’99.

10. Jon Lester, Cubs

6-year, $155 million contract before 2015 season

It wasn’t merely that Lester went 77-44 with a 3.64 ERA over six years for the Cubs. Here is all you really need to know about him: He started and was the winning pitcher for the Cubs in Game 5 of the 2016 World Series, when they were down three games to one against Cleveland and on the verge of losing a chance to win the franchise’s first Series in 108 years. No Cubs pitcher in history ever faced more pressure. Lester pitched six innings that night, giving up four hits and two earned runs while striking out five. We already knew how tough Lester was as a cancer survivor. He was never tougher as a pitcher than he was that night at Wrigley.

Honorable mention: Catfish Hunter was the first star free-agent pitcher a half-century ago. He probably belongs on this list, too.

Now we wait to see which starter might be a difference-maker this time. Starting pitching is always a big gamble, but not as big as the payout can be.