MLB Free Agency: Who Wins a 'Cheapest Owner in Baseball' Tournament Bracket?

With March Madness in full swing, and baseball season just weeks from kicking off, this is an exciting time of year for sports fans.

As general managers look to put the finishing touches on their teams heading towards Opening Day, some have been put in a better position by their owners than others. While teams like the Yankees and Red Sox seemingly have endlessly deep pockets thanks to their ownership, others are not so fortunate thanks to cheaper ownership.

So in honor of March Madness, here's my 16-team tournament to determine who is the cheapest owner in baseball.

The field was cut to 16 by eliminating the 13 teams with payrolls in excess of $100 million, and then dropping three more teams. That left me with eight teams each from the NL and AL, and those teams were seeded 1-8 based on their projected 2012 payrolls, with the largest payroll receiving a No. 8 seed and the smallest a No. 1 seed.

So here is how my cheapest owners in baseball tournament shakes out.

$100 Million Payroll Club

$100 Million Payroll Club (projected numbers via Yahoo!)

New York Yankees ($204 million) - Hal Steinbrenner
Philadelphia Phillies ($170 million) - David Montgomery
Boston Red Sox ($167 million) - John Henry
Los Angeles Angels ($140 million) - Arturo Moreno
Detroit Tigers ($132 million) - Mike Ilitch
San Francisco Giants ($129 million) - Bill Neukom
Texas Rangers ($118 million) - Chuck Greenberg
St. Louis Cardinals ($111 million) - Bill DeWitt Jr. 
Chicago Cubs ($105 million) - Ricketts family
Los Angeles Dodgers ($103 million) - Frank McCourt (lame duck owner)
Miami Marlins ($100 million) - Jeffrey Loria

Any team with a payroll eclipsing $100 million can hardly be considered to have an owner who is holding too tightly to the purse strings, so the 13 teams with payrolls that high were automatically disqualified from the tournament.

It is most of the teams you would expect, with the notable newcomer to the group being the Marlins, who were all too well known for their fire sales following World Series titles in 1997 and 2003. Now, with a new stadium set to open, the team is spending like never before and no longer ranks among the small market clubs.

Last Three out

Last Three Out

Chicago White Sox ($98 million) - Jerry Reinsdorf
Atlanta Braves ($90 million) - Liberty Media
Washington Nationals ($89 million) - Lerner Enterprises

To cut the field to 16, three teams below the $100 million threshold also had to be left off, and the White Sox, Braves and Nationals were the choices.

While they look to be headed for a rebuild, the White Sox roster is loaded with big contracts and the team has never been afraid to make a big signing or trade for a big contract.

The Braves aren't thought of in the same breath as the big market giants, but that is largely because they are so good at developing homegrown talent. They keep their players around and sign who they need to.

Finally, like the Marlins above, the Nationals are new to the ranks of spenders, but after ponying up for Jayson Werth last season and signing Edwin Jackson along with extending Gio Gonzalez and Ryan Zimmerman this offseason, the team looks ready to spend what it takes to win.

That leaves us with 16 teams, eight from the NL and eight from the AL, so the bracket will be divided by league. Now for a look at the seeds.

NL Round One: No. 1 Pittsburgh Pirates vs. No. 8 Milwaukee Brewers

No. 1 Pittsburgh Pirates ($46 million) - Robert Nutting

Over the last few years, the Pirates have developed some solid talent, only to trade those players off prior to signing them to an extension. That has resulted in a losing record for the team every year since 1992.

However, the team spent some money this offseason in adding veterans to fill out their roster, and signed star center fielder Andrew McCutchen to a six-year extension.

No. 8 Milwaukee Brewers ($98 million) - Matt Attanasio

While the Brewers were unable to re-sign superstar first baseman Prince Fielder this offseason, the team did spend money in bringing in third baseman Aramis Ramirez and shortstop Alex Gonzalez. Also, the team is moving towards re-signing starters Zack Greinke and Shaun Marcum.

Winner: No. 1 Pittsburgh Pirates (but not by as big a margin as in years past)

NL Round One: No. 2 San Diego Padres vs. No. 7 New York Mets

No. 2 San Diego Padres ($53 million) - Jeff Moorad

The Padres were forced to deal slugging first baseman Adrian Gonzalez last offseason prior to him hitting free agency, as they had no chance of re-signing him, and they again lost an All-Star this offseason when closer Heath Bell signed with the Marlins.

The team had a busy offseason, adding a number of prospects while also trading for White Sox slugger Carlos Quentin. Still, with more money to spend in the years to come this is a team that could be great, but it remains to be seen if that will happen.

No. 7 New York Mets ($93 million) - Fred Wilpon

The Mets failed to re-sign shortstop Jose Reyes this past offseason, and have parted ways with big money veterans Carlos Beltran and Francisco Rodriguez among others, as their payroll has dropped $49 million, down from $142 million last season.

However, that is less an indication of the team's lack of spending and more a sign that the team is beginning to rebuild. Within a few seasons the team will likely be spending once again as they start to build around a solid young core, but for now they won't be looking to spend.

Winner: No. 2 San Diego Padres

NL Round One: No. 3 Houston Astros vs. No. 6 Cincinnati Reds

No. 3 Houston Astros ($61 million) - Jim Crane

The Astros are in the midst of a full-scale rebuild, as they have traded off veteran talents Hunter Pence, Michael Bourn, Lance Berkman and Roy Oswalt over the past few seasons.

They will likely look more like a Triple-A team this coming season, and their cost-cutting was a combination of the team needing to rebuild and the team being up for sale and more attractive with a lower payroll.

They have spent in the past, and time will tell if they become big spenders again down the road, but for now don't expect much in the way of spending.

No. 6 Cincinnati Reds ($85 million) - Robert Castellini 

The Reds have always spent fairly well, and after locking up Jay Bruce last offseason the team is working to bring back Joey Votto and Brandon Phillips on big extensions.

Some free agent signings haven't gone particularly well, as Bronson Arroyo and Francisco Cordero were overpaid, to say the least, but still the Reds are far from a small market team.

Winner: No. 3 Houston Astros

NL Round One: No. 4 Arizona Diamondbacks vs. No. 5 Colorado Rockies

No. 4 Arizona Diamondbacks ($75 million) - Ken Kendrick

The Diamondbacks were the surprise playoff team of the year last year, as what looked like an average team on paper managed to capture the NL West title.

All in all, the team has relied more on homegrown talent, the trade market and bargain hunting to put together their roster. So while the team has not necessarily been big spenders, they have no real need as of late.

No. 5 Colorado Rockies ($80 million) - Charlie Monfort

The Rockies had a busy offseason, adding a number of veterans to fill some of their more obvious roster holes, but they are still lacking in proven starting pitching.

Key players Troy Tulowitzki and Carlos Gonzalez have been locked up on long-term deals, but if the Rockies are to take the next step from competitive team to championship contender, they may need to be willing to spend a little bigger.

Winner: No. 4 Arizona Diamondbacks

AL Round One: No. 1 Oakland Athletics vs. No. 8 Minnesota Twins

No. 1 Oakland Athletics ($51 million) - Lewis Wolff

While Moneyball served as a window into just how cheap the Athletics are for the casual fan, the team has long been watching as veteran stars walk in free agency or are dealt.

This offseason in particular was an indication of just where the franchise is at financially, as the team dealt a pair of young pitchers in Trevor Cahill and Gio Gonzalez for even younger players.

The team looks to be in a consistent state of rebuilding, and there is no let-up in sight.

No. 8 Minnesota Twins ($98 million) - Jim Pohlad

The Twins opened a new stadium prior to the 2010 season and ushered it in by re-signing superstar catcher Joe Mauer to a eight-year, $184 million. However, this past offseason they watched as outfielders Michael Cuddyer and Jason Kubel left in free agency and replaced them with Josh Willingham and Ryan Doumit.

Once an annual contender in the AL Central, the Twins now look to be headed for a rough patch.

Winner: No. 1 Oakland Athletics

AL Round One: No. 2 Kansas City Royals vs. No. 7 Toronto Blue Jays

No. 2 Kansas City Royals ($58 million) - David Glass

The Royals have long been the doormats of the American League, but the team has built a young core that is the envy of teams league-wide. 

They are without a legitimate frontline starting pitcher, but they are heading in the right direction and should be a contender within the next couple seasons. They are by no means big spenders, but they have made the most of their assets and have built their team the right way.

No. 7 Toronto Blue Jays ($82 million) - Rogers Communications

Playing in the AL East, the Blue Jays are a good team that has no chance of making the postseason any time soon. They had a .500 record last season, yet finished fourth in their own division and 16 games out of first place. 

Rumors swirled this offseason that the team would be big players for Prince Fielder and Japanese pitcher Yu Darvish, but in the end they failed to make the big move. The owners have the money to spend, but to this point they have yet to make the moves necessary to contend.

Winner: No. 7 Toronto Blue Jays

AL Round One: No. 3 Tampa Bay Rays vs. No. 6 Seattle Mariners

No. 3 Tampa Bay Rays ($62 million) - Stuart Sternberg

With a payroll that ranks among the lowest in the league, the Rays have managed to compete with the Red Sox and Yankees in recent seasons, thanks almost entirely to some fantastic player development.

Last offseason, the team was forced to watch as Carl Crawford, Carlos Pena and their top seven relief pitchers all departed in free agency. Despite all that, the team made the postseason again last year, and just imagine what the team could do with some money to spend.

No. 6 Seattle Mariners ($80 million) - Nintendo

The Mariners were the worst team in the American League last season, and with a payroll that ranked in the upper half of the league.

The team has begun to incorporate some young talent into their lineup, and they have cut their payroll from over $100 million in 2008 to roughly $80 million. After watching free agents like Chone Figgins, Carlos Silva, Richie Sexson and others flop in recent seasons, the team could be moving towards relying more on player development than on spending.

Winner: No. 3 Tampa Bay Rays

AL Round One: No. 4 Cleveland Indians vs. No. 5 Baltimore Orioles

No. 4 Cleveland Indians ($67 million) - Larry Dolan

The Indians made the questionable decision to bring back Grady Sizemore this offseason on an incentive-laden deal, but for a team that needed a shot in the arm offensively they didn't do nearly enough.

The team has always had a low payroll, and with some talented young players and playing in the AL Central the team could contend given a bigger payroll and the ability to add some much-needed offense. However, the team has not made a significant free agent addition in years.

No. 5 Baltimore Orioles ($73 million) - Peter Angelos

The Orioles have been as active as anyone the past few offseasons, adding Derrek Lee, J.J. Hardy, Mark Reynolds and Vladimir Guerrero last winter and playing the international market in signing Wei-Yin Chen and Tsuyoshi Wada this offseason.

It won't be enough to contend in the ridiculously deep AL East, but the team is doing its best to put a competitive team on the field for its fans and has improved over the past few seasons.

Winner: No. 4 Cleveland Indians

NL Round 2 and 3 Results

No. 1 Pittsburgh Pirates vs. No. 4 Arizona Diamondbacks

While the Pirates should once again be competitive, they are lacking in the starting pitching department, and adding Erik Bedard and A.J. Burnett did not exactly push their rotation to the upper tier.

Winner: No. 1 Pittsburgh Pirates

No. 2 San Diego Padres vs. No. 3 Houston Astros

Given the direction the Astros are heading and the fact that their new ownership has no history of spending to this point makes Houston the pick over a Padres team that has shown a willingness to at least add veteran pieces in the past few seasons.

Winner: No. 3 Houston Astros

No. 1 Pittsburgh Pirates vs. No. 3 Houston Astros 

Owner Robert Nutting has been at the helm in Pittsburgh since 2007, and since then the team's payroll has not changed much. However, they have begun to spend more wisely, and with a good core in place, adding small pieces here and there while waiting for their key prospects to arrive may be their best course of action.

Meanwhile, in Houston, the team was forced to cut payroll and move promising young players like Hunter Pence and Michael Bourn before owner Jim Crane would purchase the team. That stipulation coupled with what will likely be a long next several seasons makes the Astros the pick here.

Winner: No. 3 Houston Astros

AL Round 2 and 3 Results

No. 1 Oakland Athletics vs. No. 4 Cleveland Indians

The Athletics have moved toward relying almost entirely on homegrown talent, which is a move that many small market teams use to be competitive. However, their dealing of pitchers Trevor Cahill and Gio Gonzalez are troubling to say the least, and there is no letup in sight as far as their on-going rebuild effort is concerned, as ownership seems perfectly content continuously flipping players for prospects.

Winner: No. 1 Oakland Athletics

No. 7 Toronto Blue Jays vs. No. 3 Tampa Bay Rays

In a match-up of two teams, it is a question of going with the team that is on the cusp of contention but has not done what's necessary to take the next step (Blue Jays) or the team who has contended over the past few seasons but continues to lose players in free agency (Rays).

I'll go with the Blue Jays here, as the Rays have no reason to spend when they can compete without breaking the bank.

Winner: No. 7 Toronto Blue Jays

No. 1 Oakland Athletics vs. No. 7 Toronto Blue Jays

It was a good run for the Blue Jays, but the dominance of the Athletics' never-ending rebuild is too much for the Cinderella Blue Jays, as the Athletics are the clear choice here as the cheapest ownership in the American League.

Winner: No. 1 Oakland Athletics

Winner (Or Is It Loser?)

No. 3 Houston Astros vs. No. 1 Oakland Athletics

While the future looks bleak in Houston, and the payroll cutting will likely continue into this season with potential trades of Wandy Rodriguez, Brett Myers and Carlos Lee coming up, the clear choice here is the proven entity.

The Athletics are the definition of a small market club, but they take it a step further, as they seemingly put winning on the back burner in favor of cutting costs and saving money at every opportunity.

So there you have it. Lewis Wolff, John Fisher and the Athletics ownership group takes the title for cheapest owners in all of baseball.