“Former Professional Tennis player” is something that’s been on my resume for the last five years. Is it true?

Kind of.

It was September 2012. After four long years, I was now officially a lawyer.

I just didn’t have a job.

I spent my days job hunting (or at least that’s what I told my girlfriend when she asked).

I did have some free time though. Well, a lot of free time. Enough time to ponder if there were any alternate careers I should be considering.

I had always wondered how a person becomes a pro tennis player. Upon doing some research, I discovered that Futures tournaments were the lowest level of ATP professional tournaments.

If not enough people had signed up, a person with no official ranking (me) might gain entry to the Qualifying Draw of a Futures Tournament.

It turned out that there were three Futures tournaments in Toronto that year. And they happened to be the next three weeks!

It felt like destiny was knocking at my door.

The first one was at the Donalda Club on clay courts. I’d never played on clay before, but I always thought I’d be great on clay.

Could I make it as a professional tennis player? Well, I was the best player in my immediate family. (Only my father played, and he was now 58.) I was even better than most of my friends.

What the hell, I thought. I’ve got nothing to lose.

On Friday, I went to the Donalda Club in Toronto to sign up for my first professional tournament. As it turned out, there were spots left in qualifying. I was going to play!

That night, I went to the official ATP website to check out the qualifying draw. My first round opponent was Josh Graves. Through research, I found a person named Josh Graves online with the following profile:

This Josh Graves had just graduated from Northwestern in April. He was beginning his (real) professional career. I really hope the Josh Graves I’m playing didn’t go to Northwestern, I thought.

I didn’t get much sleep that night. With dreams of tennis glory, I arrived at the Donalda Club the next morning.

I realized pretty quickly that I might be out of my element.

The other players were ripped 18-year-olds with thighs of steel. I was an unshaven 27-year-old with a slight beer belly.

The other players had coaches. I had gotten word from my brother that he’d come watch me play if he was free.

The other players had Nike headbands, official gear and carried multiple racquets.

I had a 2007 Toronto Raptors playoff t-shirt with a couple of holes in it, a plastic bag to carry some of my things, and only one racquet. Oh shit, what if my strings break, I thought.

The other competitors looked at me confused.

Trying to avoid their glances, I found my first-round opponent, Josh Graves.

“Hey, did you go to Northwestern?” I asked him.

“Yup,” he said.

Damn.

“How did you know?” he asked.

“Umm….” I hesitated. I didn’t respond. Usually I can talk my way out of an awkward situation (a skill that comes from being someone who creates a lot of awkward situations). Nothing came to mind.

During the warm-up, I could sort of rally with him. I’m not sure if this was because I was close to his level, or if he was just being kind to me.

When the match started, my dreams of glory were quickly dashed. Graves belted every shot deep on the base line. If I left a ball short, Graves crushed a winner.

I felt badly for Graves. He had just spent the last four years battling on the American college circuit. I don’t think I was what he envisioned when he decided to begin his professional career.

During changeovers, I looked down, too embarrassed to make eye contact with my opponent. I awkwardly explained to Graves that I was a lawyer. In other words, “I know I’m terrible, but this isn’t what I do full-time!” Good thing he didn’t ask me where I worked.

Mercifully, the match ended in about 40 minutes.

6-0, 6-0.

I probably won about 4 points throughout the whole match. I wished Graves good luck, and left the Donalda Club with my tail between my legs.

I didn’t sign up for the Futures tournament the next week. Clearly my aspirations as a tennis player had been slightly absurd.

The following week came along, and my job search was going almost as badly as my tennis career.

There was still one Futures Tournament to be played in Toronto. I had the time. I mean, it couldn’t be any worse.

It was a familiar scene walking into Mayfair Clubs that Saturday morning. Ripped teenagers, coaches. The feeling of being a square peg in a round hole.

There was a middle-aged parent sitting amongst the teenagers. “Whose your son?” I asked him.

“Huh,” he replied.

Then I noticed a tennis bag at his feet. Wait. Was he playing? Was he the older version of me?

“Are you playing today?”

“Yup,” he said with a satisfied grin.

I introduced myself to him. I discovered that his name was Paul, and he was 50 years old. In his free time, he traveled to places like Rochester and Gatineau to play ATP qualifying matches. He had not fared particularly well.

I went to checkout the draw. I saw that I was playing Paul Woolam.

Please let his last name be Woolam. Please let his last name be Woolam.

“So it looks like I’m playing Paul Woolam,” I said.

“That’s me!” Paul replied.

“Oh nice,” I said calmly while desperately trying to contain my excitement.

We were assigned to Court 4.

We arrived on court, and began stretching. We looked over to the other courts and noticed a slight contrast between ourselves and the other first-round competitors.

On courts One to Three were 19-year-olds with powerful serves and blistering forehands.

On court 4 was a slightly overweight, unemployed ‘lawyer’ and a 50 year old from Pembroke, Ontario.

People in the stands probably looked out on the courts and thought, OK, courts 1 to 3 are the professional courts, and Court 4 is the recreational court.

Nope, all professional courts!

After I grabbed an early 2-0 lead, Paul hammered a couple of serves that I couldn’t grab a hold of. He held serve, and sported an excited grin as we walked to the net to change sides.

“First ATP Game!” Paul exclaimed. We high-fived. This was not going to be a typical match.

Paul was pretty mobile for an ‘old man’, hustling to return every ball.

Throughout our match, Paul and I laughed during changeovers, congratulated each other on winners, and frankly, couldn’t believe our luck that we had gotten to face each other.

The formal nature of our match was also pretty cool. I mean, it wasn’t every tennis match we played that people would bring us new balls every nine games.

After winning the first set 6-4, the second set went to a tiebreak. I had a match point at 6-5. I double-faulted, and Paul went on to win the tie-break 8-6 to even the match at one set apiece.

It was turning into an epic affair.

I’m not sure the tournament officials felt that way though.

Throughout our match, I had noticed eye-rolls, and glaring stares coming our way from the ITF staff. I don’t think we were what they had in mind when they had invited spectators to come watch some professional tennis on a Saturday morning.

After the 2nd set tiebreak, an ITF representative came over to our court.

“Match over?” He asked me.

“No. Paul just won the 2nd set tiebreak. We’re going to a 3rd set.”

He did not look happy.

He walked back to the sidelines, and broke the unfortunate news to the tournament director. I noticed a heated discussion between the two of them. The tournament director glared in our direction.

The third set was full of drama. At 5 all in the 3rd, Paul’s back was cramping up.

He called for an official Medical Time Out. Ok, he didn’t do that.

But he did receive a massage from the tournament medical personnel.

Paul kept fighting, but his movement was clearly hampered. I took the next two games, and took the decisive third set 7-5.

I had done it. I had won an ATP Match.

For the rest of my life, I could declare that yes, I had won a professional tennis match.

Who was my opponent in the 2nd round? Who else? Josh Graves.

This time, I put up more of a fight.

Oh, don’t get me wrong. I still lost 6-0, 6-0.

But I had 3 game points on my serve. To this day, I still rue those missed opportunities. It could’ve been a 6-0, 6-1 loss!

Walking away from the court, despondent after another Josh Graves shellacking, a friend of mine lifted my spirit with some words of encouragement.

“Pete, you gotta stop playing these Futures Tournaments. This is getting embarrassing.”

Soon after that fateful day, I was offered a job as an associate at a law firm.

Against my better judgment, I accepted the job, and decided to retire from professional tennis.

As a lawyer, my colleagues would have fun with my ATP History.

According to them, I had constant nightmares about Josh Graves.

“Graves!” they would exclaim, in the same way that Seinfeld would say “Newman”.

They drew some beautiful artwork on my white board to commemorate my previous career.

When I joined my colleagues for lunch, they would take great joy in my presence and say, “Wow, thanks for coming. It’s such an honour to be joined by an ATP player”.

When the Futures tournaments came to Toronto every year, my tennis friends would ask me if I’d been given a Wild Card into the events.

I may have been the butt of a lot of jokes, but when you do a google search for ‘Peter Mendelsohn tennis’, this is what you find:

Guess I’m not lying on my resume after all.