Those who’ve followed the world of major league baseball for a few years cannot have failed to be drawn into the world of fantasy baseball. In its traditional form, known as “roto”, an auction or draft is held so that each real life player can be owned by only one player in the league. This is substantially different than the salary-cap style game preferred by those who indulge in fantasy premier league soccer. The ability to trade players between teams is just one aspect that makes this type of league more enjoyable, and with trading comes trade deadline day.

The league in question is one of long standing, now in its 12th year of play, with members from California to Toronto to Dublin (me). To add depth and intrigue even for the teams that aren’t in the title hunt, in this kind of league each team can keep seven players from year to year along with a further five prospects (young players who still have “rookie” status in MLB).

From early the 2011 season I reckoned that I’d be in the frame for a run at the title. Paul Konerko, aging White Sox first baseman was rolling back the years and hitting the cover off the ball while James Shields was pitching like the staff ace some thought he always should have been. I made a couple of trades in June to add Matt Holliday, Matt Cain and Andrew Bailey. Hideki Matsui, elderly Oakland DH, was added; he started to hit like Ted Williams and wouldn’t let up. Things were going swimmingly.

Come mid July however and half of my team would conspire to take a sudden dive like a crooked middleweight. The two teams at the top eased away.

The arrival of a third team into the mix, leapfrogging me with depressingly little effort, gave me the feeling that there would be a market for a determined seller at the trade deadline.

The goal of each contender would be to win the league without entirely mortgaging the future. Still, flags fly forever and in a league of such quality and long standing being crowned champ carries no small amount of kudos.

In my locker I had 10 keeper-worthy players, three of which would be useless to me when it would become time to declare our seven keepers for 2012. Alongside these there were also another 8 solidly good players that no team would ideally keep but in the context of the remaining seven weeks of MLB action could be of significant value to one or more of the three contenders.

The rub was that these players would only be assets until 23:59 Pacific Time on August 14th (8am GMT on the 15th). After that, they would be worthless.

Keeper-Quality players (10)
Joe Mauer
Matt Holliday
Josh Hamilton
Tim Lincecum
A-Rod
Matt Cain
James Shields
Jonathan Papelbon
Mike Cuddyer
Danny Espinosa

Other Players of Value to Someone (8)
Paul Konerko
Hideki Matsui
Ichiro Suzuki
Cory Hart
Gaby Sanchez
Andrew Bailey
Ricky Romero
Max Scherzer

My goal was to convert these assets into future draft picks, a quality prospect and, hopefully, to pull back one of the best players in baseball as a major keeper upgrade.

Importantly, I reckoned that the three contenders might have a more than usual amount of motivation:

– Team A had trailed for the season and had only recently gone top of the table by a mere half point. With just 45 days of the season remaining, gaining a key player might keep him there.

– Team B had led from Opening Day, mostly by a long, long way. I knew he’d want to pay in order to get that lead back; being human he would have probably assumed as far back as June that the title was in the bag.

– Team C had made a consistent run over the past two months which, if continued, would definitely put him within a stone’s throw of the title. His team was on fire but an extra piece or two could put him over the top. Overtaking the two guys who’d been ahead for so long would rank as an impressive feat.

This was potentially a healthy market. However, a market can take various forms. Sometimes it’s a small but hectic market stall with multiple buyers haggling over the same asset; the price will rise and rise for that particular asset but can end up sucking the air out of any other negotiations. Other markets are like a large bazaar where prices are lower but more business is done.

As I had so many assets to move – ideally as many as eleven players – having a bidding war over a single player might not do me much good in the long run. Instead I did my best to gently guide each negotiation towards different groups of players in the hope that each wouldn’t settle on a shared all-or-nothing goal of the same shiny object.

Gentle feelers were sent out early in the week. At first glance, only Teams B (Matt Kemp) and C (Andrew McCutcheon; Carlos Gonzalez) could satisfy my primary objective of wrestling free a young hitting stud. Still, I might be able to squeeze some draft picks out of Team A.

The week’s emails rolled along until finally, Sunday morning, the arrival of deadline day.

Sometimes life is serendipidous: on Saturday Team B lost Logan Morrison, outspoken but usually semi-competent Marlins’ outfielder, to a surprise demotion by the Floridian powers that be. This did my cause no harm whatsoever; however badly LoMo had been playing of late, this was now a gaping hole in Team B’s lineup at a time when he simply couldn’t afford it.

Negotiations opened early on Sunday with all three teams. One by one, prospective deals hove into view over the day only to be dashed by some disagreement over a final detail over which there would be no budging.

With a title on the line, however, sooner or later something would have to give.

Fortunately the PGA golf championship was going down the wire so I had ample entertainment available while my three trading partners sweated.

At 17 minutes past midnight (GMT) my email inbox pinged into life. A short note had arrived from Team B, accepting the trade that I’d let him stew over while I’d earlier enjoyed a good meal and a bad film. My prize: Matt Kemp, richly gifted outfielder for the LA Dodgers whose fabulous play this season (.320 batting average, 28 home runs and 31 steals so far) and young age (26) had made him a big target for me.

Also coming my way would be the young Kansas City uber-prospect Bubba Starling. Hell, he might have chosen to reject the Royals’ offer and play football but with his talent ceiling it was a risk worth taking. He and his agent Scott Boras made me sweat though, holding out until the last minute to sign with Kansas City late on Monday night.

In return I would send some significant pieces: slugger Matt Holliday, pitcher Matt Cain, the surprising Paul Konerko and the talented but brittle closer Andrew Bailey.

In isolation I might not have done this deal – Holliday and Cain are very solid keepers in their own right – but in a keeper league players like Kemp simply don’t shake loose from their owners very often; when you see a chance to get them you go for it. Besides, this was not about one deal but instead about maximising all of my assets.

The wheels were now in motion.

12.19am: No sooner had the Kemp trade been announced than Team B announced a second trade; he had acquired the great Albert Pujols, future Hall of Fame first baseman for St. Louis.

This was stunning. Two blockbuster trades, one after the other.

While in real life the ESPN “Trade Deadline Special” studio would have gone nuts, in the parallel universe of this fantasy league the second trade from Team B put a huge squeeze on Teams A and C. Beforehand, they might have chosen to sit tight and trust to luck or a late free agent pickup; now if they wanted to make a serious run at the title they’d definitely have to reload, and fast.

12.23am: Team C wanted a couple of arms with a chance to pick up some wins down the stretch. I agreed to send him Max Scherzer and Ricky Romero, talented but unkeepable pitchers, in return for a 10th round draft pick.

2.05am: Team A needed some steels and an upgrade at his corner infield spot. From my stable he plucked Ichiro Suzuki, underperforming but still speedy Japanese legend, plus the limited Florida first baseman Gaby Sanchez. A 7th round draft pick comes my way.

2.41am: Team C inquired if Milwaukee outfielder Corey Hart might be available for a mid-round pick? Bye bye Corey, I’ll put that 13th round draft pick in the bank.

2.52am: Team A noticed that I’d put a message on the league website saying that pitchers James Shields and Jonathan Papelbon, keeper calibre players both, were available. We agree on a fee of a 4th round pick for Shields.

2.58am: I offered Papelbon to Team A for a 6th round pick; I know that a) he needs to try and make ground in saves to stay ahead of Team B’s new Pujols/Holliday/Cain/Konerko/Bailey juggernaut and b) his third closer, Kyle Farnsworth, is viewed as being notoriously flaky. Even ignoring those factors it’s a good price as Pap is certainly a keepable player. The owner knows this, even though it’s yet another draft pick he’s losing to me, and accepts.

The wires are now cold.

Only Matsui was left; surprisingly as he’d been hitting the best of the lot. In my mind’s eye the venerable Japanese had arrived at the bus station but saw the big Greyhound already easing onto the interstate. He’s stuck here.

The net total of all trading was a nice little haul. Danny Espinosa might not be everybody’s cup of tea as a keeper but I’ll flip him in the offseason for a bigger fish.

1) My Seven Keepers (with offseason trading to come):
Kemp
Mauer
Hamilton
Lincecum
A-Rod
Cuddyer
Espinosa

2) Extra draft picks in the 4th, 6th, 7th, 10th and 13th rounds

3) The rights to Kansas City prospect Bubba Starling.

My deals done, I waved adieu to my guys, wished the three contenders the best of luck in their sprint to the finish and now look forward to an offseason where I’ve got plenty of ammo to set up a run at the 2012 title.

3.05am: I went to bed, mind buzzing. Only one untraded piece out of 11; that’s a job well done.

3.30am: Damn it, I’m still awake.

3.40am: Damn it, why the hell couldn’t I have got even a 15th rounder for Matsui?

3.45am: ZZZZzzzzz….