What type of team typically gives out a mega-deal?

The Winter Meetings are over, and we still don't know where Bryce Harper or Manny Machado are going to end up.
Maybe Harper goes to the Phillies, or the Yankees, or the Cardinals, or the Dodgers or back to the Nationals. Machado fits with the Phillies and Yankees too, and we know that the ever-present "mystery team" looms for both. Players this young and talented simply don't reach the market very often; to be totally honest, you could make an argument for all 30 teams to sign one or both.
That includes the White Sox, who just went 62-100 and haven't had a winning season since Adam Dunn, Paul Konerko, and a 23-year-old Chris Sale led the 2012 crew to a second-place finish. They stand out because they've expressed interest; they've regularly been mentioned as being in the race for Harper and Machado this winter and they apparently attempted to acquire Machado last offseason and at the July Trade Deadline.
The White Sox want one of them despite the fact that they've been unsuccessful. They want them because they've been unsuccessful. Even if it's not likely that Harper or Machado alone would vault Chicago into contention in 2019 (especially since the club is currently projected to be in a three-way tie at the bottom of the American League Central), it certainly makes sense why it is interested. The White Sox haven't been good because they don't have enough good players. Why not start by getting the best available player(s) -- especially ones who are young enough to still be in their primes when Chicago is ready to contend in a year or two or three? 

We're talking about Chicago here because it has shown interest, but this really goes for any sub-.500 team: You don't have to expect to contend for a title in 2019 to want to add an elite young talent. But, the thinking goes, Harper and Machado want to win. Harper has never won a playoff series. Machado hadn't before joining the Dodgers late in 2018. They won't go to a team that didn't win.
Perhaps. But is that really true? Think about all the variables that go into a decision this momentous. Sure, winning is important. So are location, fit with the organization, ballpark, teammates, coaches and so on. But in the end, we all know the most important factor here is money. They're going to go where they can get the largest contract, and they've earned the right to do so. 
In order to test this theory, we decided to look back at the largest free-agent contracts in history to see how many players ended up signing mega-deals with teams coming off losing seasons. (For the purposes of this exercise, we're only looking at players who signed contracts with new teams, not extensions with current teams, like the ones signed by Giancarlo Stanton, Miguel Cabrera, Clayton Kershaw and Joey Votto.)
We found 35 contracts of at least $100 million signed by free agents headed to new teams, over a period spanning December 1998 (when the Dodgers made Kevin Brown the first $100 million player) and last week (when the Nationals signed left-handed starting pitcher Patrick Corbin to a $140 million pact). Let's see how they break down.
The breakdown: Losing teams can and do sign star free agents
Four of the seven largest contracts in baseball history came with clubs that were coming off losing seasons. (Those would be Alex Rodriguez with the Rangers in 2001, Robinson Canó with the Mariners in '14, and Zack Greinke and David Price with the D-backs and Red Sox, respectively, in '16.)
That's four of the top seven, and eight of the top 20. It's 10 of the top 25, and 13 of the entire 35. That is, nearly 40 percent of the time a team has signed a free agent to a contract of $100 million or more, that team is coming off a losing season. Four of the winning teams were 82-80, meaning just under half of these mega-deals went to teams that won no more than 82 games. 
(Not all losing seasons are the same, we understand. Some teams are in the midst of deep rebuilds, and some stumbled to 79-83 seasons. For simplicity, this is where we're drawing the line.) 
Of the 35 contracts, the average winning percentage of teams the previous season was .511, or something like 83-79. Of course, the distribution in there is all over the map. The weakest team to sign a nine-figure player was when the 2007 Cubs, coming off a last-place, 66-96, disaster in 2006, signed Alfonso Soriano to a $136 million contract. The strongest team was also the Cubs, in this case signing Jason Heyward to a $184 million deal after finishing 97-65 in '15. (That's tied with the '11 Phillies, who also went 97-65 in '10 then added Cliff Lee for $120 million.) The most recent was Eric Hosmer, to San Diego last year.

Unsurprisingly, the Yankees have signed the most $100 million free agents -- five -- ahead of the second-place Cubs and Red Sox, at four each. Since New York simply does not have losing seasons -- it hasn't happened since 1992 -- things are a little skewed. If we remove the Yankees, we're looking at 13 of 31 nine-figure contracts going to losing teams, or just better than 40 percent.
The point is, it can happen. It can happen because it has happened. 
The deals signed with teams coming off losing seasons
OK, so what did those 13 nine-figure deals with teams coming off subpar years look like? In descending order of contract value... 
$252 million, Alex Rodriguez, Rangers, 2001
A-Rod was fantastic in three years with Texas, hitting .305/.395/.615 with 156 homers and three top-six Most Valuable Player Award finishes, but the Rangers never finished above fourth, and he was famously traded to the Yankees prior to the 2004 season.
$240 million, Robinson Cano, Mariners, 2014
The first five years of Cano's contract have been productive (.296/.353/.472), though he was unable to help Seattle break its long stretch of missing the playoffs. The next five years belong to the Mets, who traded for him (but mostly Edwin Díaz) this offseason.
$217 million, David Price, Red Sox, 2016
It's odd to think of the Red Sox as a "losing team," but Boston actually finished in last place in the AL East in 2012, '14, and '15. Of course, the Red Sox won the World Series in '13 and '18, and it's fair to say that Price's contribution to this year's title winners completely turned around the perception of this contract.

$206.5 million, Zack Greinke, D-backs, 2016
Coming off 98- and 83-loss seasons, the D-backs beat out the Dodgers and Giants to sign Greinke, and he's been effective in three years in Arizona. The team's results have been inconsistent, though; they went 69-93 in his first season, then won 93 games and the NL Wild Card Game in 2017. He's reportedly on the trading block this winter.
$155 million, Jon Lester, Cubs, 2015
This is an example where the previous season's record doesn't tell the full truth. The 2014 Cubs went 73-89 but were much better in the second half as Jake Arrieta broke out, and it was clear the young group led by Kris Bryant and Anthony Rizzo was ready to explode. They've won at least 92 games in each of the four years Lester has been there.
$144 million, Eric Hosmer, Padres, 2018
Despite Hosmer's market seemingly dwindling to only the Royals and Padres, San Diego gave Hosmer the richest deal in franchise history, and the first year was disappointing for both player (.253/.322/.398) and team (66-96). There's still plenty of time for this one to turn around, of course.
$136 million, Alfonso Soriano, Cubs, 2007
After a pair of losing seasons, Soriano helped the Cubs return to relevance, as they won back-to-back division titles in 2007 and '08 before fading badly, leading into the current era of dominance. Soriano stuck around until 2013, and he was an above-average hitter every year aside from an injury-plagued '09, clubbing 181 homers for Chicago.
$132.5 million, Justin Upton, Tigers, 2016, and
$110 million, Jordan Zimmermann, Tigers, 2016
Somehow, these ones were only three years ago. The Tigers slipped to 74-87 in 2015 and reloaded for '16, getting back up to 86-75 and second place in the division. Upton performed for Detroit, slugging .500 with 59 homers, but was traded to the Angels midway through '17. Zimmermann, however, has rarely been healthy, and has a 5.24 ERA for Detroit.
$126 million, Jayson Werth, Nationals, 2011
Washington had lost 298 games in the three seasons before Werth arrived, and this is often referred to as the deal that gave the Nationals legitimacy with other free agents. Whether that's true or not, they were 80-81 in 2012 and won four division titles with Werth, who was probably the best free-agent signing in franchise history.

$126 million, Barry Zito, Giants, 2007
After back-to-back third-place finishes, the Giants brought Zito across the bay from Oakland, and he never once had a season as good as he'd had with the A's. So there's that, but he was a big contributor to the 2012 World Series champions, including topping Justin Verlander in Game 1 of the World Series.
$119 million, Carlos Beltran, Mets, 2005
The 2004 Mets had a young José Reyes and David Wright, but they also lost 91 games. Beltran's first year was something of a disappointment, but he slashed a strong .280/.369/.500 in seven years with New York, though he'll likely always be remembered for watching Adam Wainwright's curveball to end Game 7 of the '06 National League Championship Series. It was the only playoff trip he made as a Met, though he's the gift that keeps giving -- when he was traded to the Giants in '11, the return was a young Zack Wheeler.
$106 million, Jose Reyes, Marlins, 2012
This was the big year for Miami, remember -- new uniforms, new ballpark and new players, as the Marlins imported Reyes and Mark Buehrle, and tried to bring in Albert Pujols, too. It didn't work. They lost 93 games, and Reyes and Buehrle were traded to Toronto after a single season.
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The point here isn't that Harper or Machado will guarantee the White Sox, Phillies, Mets, Giants, Twins, or any other team that was below .500 in 2018 a trip to the playoffs. It's that it can happen because it has happened, and quite often. It could happen in 2019, too.