Ranking the Top-10 Free Agent Signings in Twins History: 6-10

[Cody Christie]

Image courtesy of © Matt Blewett-Imagn Images

The half-century history of MLB free agency has produced plenty of excess but also moments where a single signing reshaped a franchise. The Minnesota Twins have rarely been a team that chased the most prominent names or set the market. Instead, their relationship with free agency has been deliberate, cautious, and occasionally brilliant.

Modern free agency traces back to a turning point in the winter of 1975 when arbitrator Peter Seitz ruled in favor of pitchers Andy Messersmith and Dave McNally. By playing a full season without signed contracts, the two exposed the weakness of the reserve clause and cracked open a system that had bound players to teams indefinitely. The decision completed the work long championed by Marvin Miller and Curt Flood and forever changed the balance of power in Major League Baseball.

Owners warned of chaos and competitive ruin, but what followed was simply a new path for roster building. Teams willing to spend wisely could supplement their cores without waiting years for internal development. For a market like Minnesota, that opportunity mattered even if it was rarely pursued aggressively. Working backward here is a countdown of the best free agent signings in Twins history, judged solely on what those players did after arriving in Minnesota.

10. Shannon Stewart, OF
Contract(s): 3-years, $18 million
2004-2006 Seasons: 2.3 WAR, .287/.347/.405 (.752), 97 OPS+  
Stewart came to the Twins at the 2003 trade deadline as a pending free agent. He was a catalyst for that club’s division title, so Minnesota re-signed him as a free agent and became one of the most reliable hitters of the early 2000s. He hit for average and set the table at the top of the lineup, and provided steady outfield play across multiple seasons.

 

9. Carlos Correa, SS
Contract: 1-year, $35.1 million
2022 Season: 5.3 rWAR, .291/.366/.467 (.834), 138 OPS+
The first Correa contract lands in the top-10 largely because of its brevity. Even so, his lone season in Minnesota featured elite defense at shortstop and middle-of-the-order production when healthy. It was arguably his most productive season in a Twins uniform. The opt-out capped the long-term value, but the short-term impact was undeniable.

8. Phil Hughes, SP
Contract(s): 6-years, $66 million
2014-2018 Seasons: 5.7 rWAR, 4.53 ERA, 1.32 WHIP, 95 ERA+
The Minnesota Twins signed Hughes in December 2013, hoping to revive his career in a pitcher-friendly park. After a record-setting 2014 season (16-10, 3.52 ERA, MLB-best K/BB ratio), they extended him in December 2014 for five years and $42 million, totaling $66 million over six years, though injuries later hampered his performance. The first deal was good, but the extension aged poorly.

7. Juan Berenguer, RP
Contract(s): 4-years, $2.03 million
1987-1990 Seasons: 6.4 rWAR, 3.70 ERA, 1.36 WHIP, 115 ERA+
Berenguer gave the Twins durability and effectiveness out of the bullpen for years. Relievers rarely draw much attention, but his consistency and workload made him a quiet asset during an era when stability mattered. He became a cult hero during the team’s 1987 World Series run, and the Twins continued to invest in him for multiple seasons.

6. Paul Molitor, DH/3B/1B
Contract(s): 3-years, $9.775 million
1996-1998 Seasons: 5.2 rWAR, .312/.362/.432 (.794), 104 OPS+
Molitor arrived at age 39 and immediately authored one of the greatest late-career seasons in franchise history. In 1996, he hit .341/.390/.468 (.858), led the AL in hits, and reached 3,000 hits. The hometown Hall of Famer helped revitalize the Twins in the late 1990s and eventually returned to coach in the organization after his retirement.

The Twins have never built their identity around free agency. Still, these signings show that when timing and opportunity align, the open market can deliver franchise-defining moments. Even in a cold-weather market, sometimes the right bat or arm can change everything.

Do you agree with the rankings above? Which names do you expect to be in the top five? Leave a comment and start the discussion.

 

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[Linus]

That was quite an age 39 season for Molly. 

[mikelink45]

Shannon Stewart should be at the top - what he brought to the Twins was amazing at a time when they really needed him.  He carried us to first place!

[Brandon]

1 hour ago, mikelink45 said:

Shannon Stewart should be at the top - what he brought to the Twins was amazing at a time when they really needed him.  He carried us to first place!

The trade for him did that.  I'm not sure resigning him is a top 10.  I guess the author isn't counting minor league free agents.

[old nurse]

30 minutes ago, Brandon said:

The trade for him did that.  I'm not sure resigning him is a top 10.  I guess the author isn't counting minor league free agents.

There is still room at the top for the other Stewart, Brock

hmm, can’t seem to find the post you responded to. 

[mikelink45]

26 minutes ago, Brandon said:

The trade for him did that.  I'm not sure resigning him is a top 10.  I guess the author isn't counting minor league free agents.

True - I only look at the one year - on his baseball reference page you will see that he accumulated more WAR 3.1 counting his time in Toronto, that year than any other during his Minnesota career, but what a year it was. 

Twinkie town in this posting claimed to be The best in season trade 

[mikelink45]

With nothing else to write about, I look forward to the next list and then the list of the worst signings and trades.  And the best Minnesotans to play in MLB.  Keep us interested. 

[DJL44]

Willi Castro should be an honorable mention

[strumdatjag]

3 minutes ago, DJL44 said:

Willi Castro should be an honorable mention

I’m thinking Willi won’t make the Top. 5 but he added much higher value (he was an All-Star as a Twin) than his market value before signing. 

[sweetmusicviola16]

Chili Davis has to be in the next edition along with Jack Morris and Dave Winfield. My guess is Brian Harper is also top 5. The fifth guy is eluding me at the moment. Going on a limb and guessing Mike Marshall.

I honestly would have put Berenguer ahead of Molitor and Winfield for the impact on the team. Shannon Stewart ahead of them too with an asterisk, since much of his impact could have been gauged from his first season when he was acquired via trade before he resigned with the Twins. 

[Blyleven2011]

Without seeing the whole list of ten not sure i can rank these 5 ...

I will say this , berenguer and molitor we got our monies worth ...

[Parfigliano]

Looking at the salary back then and comparing to now is crazy.  Molitor 3 yr/9.775 mil or roughly $3.25 mil per year.  A crappy utility infielder that can't OPS .715 makes millions more a year now.

[Doc Lenz]

7 hours ago, strumdatjag said:

I’m thinking Willi won’t make the Top. 5 but he added much higher value (he was an All-Star as a Twin) than his market value before signing. 

He was an All Star because the Twins had to have a selection. Best of the bunch is all.

[Doc Lenz]

Bombo Rivera is No. 1

[Twodogs]

Chilli Davis has to be on here.  Also, wasn't Bert Blyleven a free agent signing when he came back from Cleveland?  He helped win a World Series also.